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Plus, complimentary all-inclusive package + One pre-cruise hotel night + Up to $1,000 onboard credit per guest

 

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Feb 2nd 2026

ReturnsMon, Feb 9th 2026

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Jimenez, Costa Rica, Puerto Quepos, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Feb 6th 2026

ReturnsThu, Feb 12th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 6th 2026

ReturnsFri, Feb 13th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 6th 2026

ReturnsFri, Feb 20th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Admiralty Bay, Bequia, Mayreau, Soufriere Bay, Pointe a Pitre, St Maarten, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 7th 2026

ReturnsSat, Feb 21st 2026

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, Falmouth, Philipsburg

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 7th 2026

ReturnsSat, Feb 14th 2026

Nights7

Departing PortPhilpsburg

Ports of CallPhilpsburg, Charlestown, Roseau, Mayreau, Martinique, Basseterre, Gustavia, Philpsburg

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsMon, Feb 9th 2026

ReturnsTue, Feb 17th 2026

Nights8

Departing PortColon

Ports of CallColon, Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

19 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsMon, Feb 9th 2026

ReturnsSat, Feb 28th 2026

Nights19

Departing PortColon

Ports of CallColon, Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Feb 9th 2026

ReturnsMon, Feb 16th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night South American Coast Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsMon, Feb 9th 2026

ReturnsTue, Feb 17th 2026

Nights8

Departing PortColón, Panama

Ports of CallColón, Panama, Bocas Del Toro, San Andres Island, Roatan Bay Island, Belize City, Costa Maya, Cozumel

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 13th 2026

ReturnsFri, Feb 20th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, Admiralty Bay, Bequia, Mayreau, Soufriere Bay, Pointe a Pitre, St Maarten, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 13th 2026

ReturnsFri, Feb 27th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, Admiralty Bay, Bequia, Mayreau, Soufriere Bay, Pointe a Pitre, St Maarten, San Juan, St. John Island, Basseterre, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 14th 2026

ReturnsSat, Feb 21st 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Feb 16th 2026

ReturnsMon, Feb 23rd 2026

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Jimenez, Costa Rica, Puerto Quepos, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night South American Coast Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Feb 16th 2026

ReturnsMon, Feb 23rd 2026

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Quepos, Golfo Dulce, Isla Parida, Fuerte Amador, Colón, Panama

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

11 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsTue, Feb 17th 2026

ReturnsSat, Feb 28th 2026

Nights11

Departing PortCozumel

Ports of CallCozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

18 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsTue, Feb 17th 2026

ReturnsSat, Mar 7th 2026

Nights18

Departing PortCozumel

Ports of CallCozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

Inside Cabin

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 20th 2026

ReturnsFri, Feb 27th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 20th 2026

ReturnsFri, Mar 6th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Philipsburg, Pointe a Pitre, Soufriere Bay, Admiralty Bay, Bequia, Mayreau, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

28 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 21st 2026

ReturnsSat, Mar 21st 2026

Nights28

Departing PortPhilipsburg

Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg, Basseterre, Gustavia, St. John's, Pointe a Pitre, Roseau, Mayreau, Bridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown, Tobago Cays, Pigeon Island (2 Days), Castries, Cruising Pitons, Mayreau, Admiralty Bay, Bequia, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

22 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 21st 2026

ReturnsSun, Mar 15th 2026

Nights22

Departing PortPhilipsburg

Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg, Basseterre, Gustavia, St. John's, Pointe a Pitre, Roseau, Mayreau, Bridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 21st 2026

ReturnsSat, Mar 7th 2026

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg, Basseterre, Gustavia, St. John's, Pointe a Pitre, Roseau, Mayreau, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 21st 2026

ReturnsSat, Feb 28th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Feb 23rd 2026

ReturnsMon, Mar 2nd 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

9 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Feb 27th 2026

ReturnsSun, Mar 8th 2026

Nights9

Departing PortBarcelona

Ports of CallBarcelona (2 Days), Valencia, Cartagena, Gibraltar, Malaga (2 Days), Palma de Mallorca, Spanish Isle, Barcelona

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

24 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Feb 27th 2026

ReturnsMon, Mar 23rd 2026

Nights24

Departing PortBarcelona

Ports of CallBarcelona (2 Days), Valencia, Cartagena, Gibraltar, Malaga (2 Days), Palma de Mallorca, Barcelona (2 Days), Nice (2 Days), Genova, Livorno (Florence,Pisa) (2 Days), Rome, Naples, Messina, Dubrovnik (2 Days), Zadar, Venice (2 Days)

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

16 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Feb 27th 2026

ReturnsSun, Mar 15th 2026

Nights16

Departing PortBarcelona

Ports of CallBarcelona (2 Days), Valencia, Cartagena, Gibraltar, Malaga (2 Days), Palma de Mallorca, Barcelona (2 Days), Nice (2 Days), Genova, Livorno (Florence,Pisa) (2 Days), Rome

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 27th 2026

ReturnsFri, Mar 6th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, Philipsburg, Pointe a Pitre, Soufriere Bay, Admiralty Bay, Bequia, Mayreau, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

Inside Cabin

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Feb 27th 2026

ReturnsFri, Mar 13th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, Philipsburg, Pointe a Pitre, Soufriere Bay, Admiralty Bay, Bequia, Mayreau, San Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Feb 28th 2026

ReturnsSat, Mar 7th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

Inside Cabin

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

15 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 28th 2026

ReturnsSun, Mar 15th 2026

Nights15

Departing PortPhilipsburg

Ports of CallPhilipsburg, Basseterre, Gustavia, Falmouth, Pointe a Pitre, Roseau, Mayreau, Bridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Feb 28th 2026

ReturnsSat, Mar 7th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Basseterre, Gustavia, Little Bay, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Feb 28th 2026

ReturnsSat, Mar 14th 2026

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Mar 2nd 2026

ReturnsMon, Mar 9th 2026

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Mar 6th 2026

ReturnsThu, Mar 12th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 6th 2026

ReturnsFri, Mar 13th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 6th 2026

ReturnsFri, Mar 20th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St Maarten, Pointe a Pitre, Mayreau, Admiralty Bay, Bequia, Pigeon Island, Cruising Pitons, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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8 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Mar 7th 2026

ReturnsSun, Mar 15th 2026

Nights8

Departing PortBridgetown

Ports of CallBridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 7th 2026

ReturnsSat, Mar 14th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Mar 7th 2026

ReturnsSat, Mar 21st 2026

Nights14

Departing PortBridgetown

Ports of CallBridgetown, Little Bay, Pointe a Pitre, Roseau, Grande Anse, Pigeon Island, Bridgetown, Pigeon Island (2 Days), Castries, Cruising Pitons, Port Elizabeth, Bequia, Mayreau, St. Georges, Admiralty Bay, Bequia, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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15 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSun, Mar 8th 2026

ReturnsMon, Mar 23rd 2026

Nights15

Departing PortBarcelona

Ports of CallBarcelona (2 Days), Nice (2 Days), Genova, Livorno (Florence,Pisa) (2 Days), Rome, Naples, Messina, Dubrovnik (2 Days), Zadar, Venice (2 Days)

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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7 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSun, Mar 8th 2026

ReturnsSun, Mar 15th 2026

Nights7

Departing PortBarcelona

Ports of CallBarcelona (2 Days), Nice (2 Days), Genova, Livorno (Florence,Pisa) (2 Days), Rome

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Mar 9th 2026

ReturnsMon, Mar 16th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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6 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsMon, Mar 9th 2026

ReturnsSun, Mar 15th 2026

Nights6

Departing PortColon

Ports of CallColon, Bocas Del Toro, San Blas, Cartagena (2 Days), Oranjestad

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Mar 13th 2026

ReturnsThu, Mar 19th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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8 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 13th 2026

ReturnsSat, Mar 21st 2026

Nights8

Departing PortSan Juan

Ports of CallSan Juan, St Maarten, Pointe a Pitre, Mayreau, Admiralty Bay, Bequia, Pigeon Island, Cruising Pitons, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 13th 2026

ReturnsFri, Mar 20th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, Marigot, Terre-de-Haut, Mayreau, Port Elizabeth, Bequia, Pigeon Island, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 14th 2026

ReturnsSat, Mar 28th 2026

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 14th 2026

ReturnsSat, Mar 21st 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Mar 15th 2026

ReturnsSun, Mar 22nd 2026

Nights7

Departing PortOranjestad

Ports of CallOranjestad, Kralendijk, Bonaire, Pigeon Island, Cruising Pitons, Admiralty Bay, Bequia, Mayreau, Man-O-War, Tobago, Bridgetown

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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13 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSun, Mar 15th 2026

ReturnsSat, Mar 28th 2026

Nights13

Departing PortBridgetown

Ports of CallBridgetown, Tobago Cays, Pigeon Island (2 Days), Castries, Cruising Pitons, Mayreau, Admiralty Bay, Bequia, Bridgetown, Basseterre, Pointe a Pitre, Roseau, Fort de France, Mayreau, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSun, Mar 15th 2026

ReturnsSat, Mar 21st 2026

Nights6

Departing PortBridgetown

Ports of CallBridgetown, Tobago Cays, Pigeon Island (2 Days), Castries, Cruising Pitons, Mayreau, Admiralty Bay, Bequia, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Mar 20th 2026

ReturnsThu, Mar 26th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Mar 21st 2026

ReturnsSat, Mar 28th 2026

Nights7

Departing PortBridgetown

Ports of CallBridgetown, Little Bay, Pointe a Pitre, Roseau, Grande Anse, Pigeon Island, Bridgetown

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 21st 2026

ReturnsSat, Mar 28th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 21st 2026

ReturnsSat, Apr 4th 2026

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

10 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 27th 2026

ReturnsMon, Apr 6th 2026

Nights10

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, St. John's, Pointe a Pitre, Pigeon Island, St. George's, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

17 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 27th 2026

ReturnsMon, Apr 13th 2026

Nights17

Departing PortSan Juan

Ports of CallSan Juan, St. John Island (2 Days), Pointe a Pitre, Pigeon Island, St. George's, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Casa de Campo, Santo Domingo, Cartagena (2 Days), San Blas, Colon

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

24 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsFri, Mar 27th 2026

ReturnsMon, Apr 20th 2026

Nights24

Departing PortSan Juan

Ports of CallSan Juan, St. John Island (2 Days), Pointe a Pitre, Pigeon Island, St. George's, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Casa de Campo, Santo Domingo, Cartagena (2 Days), San Blas, Colon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Olbia, Sardinia, Puerto Quepos, Puerto Caldera

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 28th 2026

ReturnsSat, Apr 4th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 28th 2026

ReturnsSat, Apr 4th 2026

Nights7

Departing PortPhilpsburg

Ports of CallPhilpsburg, Road Bay, Sopers Hole, Great Harbour, Jost Van Dyke BVI (2 Days), Gustavia, Philpsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsMon, Apr 6th 2026

ReturnsMon, Apr 20th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, Casa de Campo, Santo Domingo, Cartagena (2 Days), San Blas, Colon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsMon, Apr 6th 2026

ReturnsMon, Apr 13th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, Casa de Campo, Santo Domingo, Cartagena (2 Days), San Blas, Colon

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

22 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsMon, Apr 6th 2026

ReturnsTue, Apr 28th 2026

Nights22

Departing PortSan Juan

Ports of CallSan Juan, Casa de Campo, Santo Domingo, Cartagena (2 Days), San Blas, Colon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Madero, Huatulco, Manzanillo, Puerto Vallarta

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsMon, Apr 13th 2026

ReturnsMon, Apr 20th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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15 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsMon, Apr 13th 2026

ReturnsTue, Apr 28th 2026

Nights15

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Madero, Huatulco, Manzanillo, Puerto Vallarta

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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8 Night Central America Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsMon, Apr 20th 2026

ReturnsTue, Apr 28th 2026

Nights8

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Madero, Huatulco, Manzanillo, Puerto Vallarta

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Seeker

DepartsThu, Apr 23rd 2026

ReturnsThu, Apr 30th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Apr 24th 2026

ReturnsThu, Apr 30th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, May 22nd 2026

ReturnsThu, May 28th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, May 29th 2026

ReturnsThu, Jun 4th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Jun 5th 2026

ReturnsThu, Jun 11th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Jun 12th 2026

ReturnsThu, Jun 18th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Jul 17th 2026

ReturnsThu, Jul 23rd 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Jul 24th 2026

ReturnsThu, Jul 30th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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7 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Aug 20th 2026

ReturnsThu, Aug 27th 2026

Nights7

Departing PortPapeete

Ports of CallPapeete, Moorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Aug 28th 2026

ReturnsThu, Sep 3rd 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Sep 3rd 2026

ReturnsThu, Sep 10th 2026

Nights7

Departing PortPapeete

Ports of CallPapeete, Moorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Sep 11th 2026

ReturnsThu, Sep 17th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Sep 18th 2026

ReturnsThu, Sep 24th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Sep 25th 2026

ReturnsThu, Oct 1st 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Oct 2nd 2026

ReturnsThu, Oct 8th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Oct 9th 2026

ReturnsThu, Oct 15th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Oct 23rd 2026

ReturnsThu, Oct 29th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

11 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsWed, Oct 28th 2026

ReturnsSun, Nov 8th 2026

Nights11

Departing PortSan Juan

Ports of CallSan Juan, Gustavia, Basseterre, Falmouth, Terre-de-Haut, Pigeon Island, Saint George's, Great Harbour, Jost Van Dyke BVI, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

10 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsWed, Oct 28th 2026

ReturnsSat, Nov 7th 2026

Nights10

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Falmouth, Pointe a Pitre, Pigeon Island, St. Georges, Great Harbour, Jost Van Dyke BVI, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Oct 30th 2026

ReturnsThu, Nov 5th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Nov 5th 2026

ReturnsThu, Nov 12th 2026

Nights7

Departing PortPapeete

Ports of CallPapeete, Moorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Nov 6th 2026

ReturnsThu, Nov 12th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 8th 2026

ReturnsSun, Nov 15th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 8th 2026

ReturnsSun, Nov 22nd 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 15th 2026

ReturnsSun, Nov 22nd 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 22nd 2026

ReturnsSun, Nov 29th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 22nd 2026

ReturnsSun, Dec 6th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

18 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsTue, Nov 24th 2026

ReturnsSat, Dec 12th 2026

Nights18

Departing PortBridgetown

Ports of CallBridgetown, Admiralty Bay, Bequia, St. George's, Kralendijk, Bonaire, Willemstad, Oranjestad, Cartagena, San Blas, Colon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

15 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Nov 27th 2026

ReturnsSat, Dec 12th 2026

Nights15

Departing PortBridgetown

Ports of CallBridgetown, Grande Anse, Pigeon Island (2 Days), Castries, Cruising Pitons, Mayreau, St. George's, Admiralty Bay, Bequia, Bridgetown, Road Bay, Anguilla, Cruising Pitons, Buccoo Reef (Scarborough), Admiralty Bay, Bequia, Mayreau, Kralendijk, Bonaire, Willemstad, Oranjestad

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Nov 27th 2026

ReturnsFri, Dec 4th 2026

Nights7

Departing PortBridgetown

Ports of CallBridgetown, Grande Anse, Pigeon Island (2 Days), Castries, Cruising Pitons, Mayreau, St. George's, Admiralty Bay, Bequia, Bridgetown

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 29th 2026

ReturnsSun, Dec 6th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 29th 2026

ReturnsSun, Dec 13th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Dec 3rd 2026

ReturnsThu, Dec 10th 2026

Nights7

Departing PortPapeete

Ports of CallPapeete, Moorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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16 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Dec 4th 2026

ReturnsSun, Dec 20th 2026

Nights16

Departing PortBridgetown

Ports of CallBridgetown, Road Bay, Anguilla, Cruising Pitons, Buccoo Reef (Scarborough), Admiralty Bay, Bequia, Mayreau, Kralendijk, Bonaire, Willemstad, Oranjestad, Cartagena (2 Days), Bocas Del Toro, San Blas, Panama Canal Daylight Transit, Panama, Balboa

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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8 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsFri, Dec 4th 2026

ReturnsSat, Dec 12th 2026

Nights8

Departing PortBridgetown

Ports of CallBridgetown, Road Bay, Anguilla, Cruising Pitons, Buccoo Reef (Scarborough), Admiralty Bay, Bequia, Mayreau, Kralendijk, Bonaire, Willemstad, Oranjestad

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Dec 4th 2026

ReturnsThu, Dec 10th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 5th 2026

ReturnsSat, Dec 12th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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7 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 6th 2026

ReturnsSun, Dec 13th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 6th 2026

ReturnsSun, Dec 20th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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7 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Dec 10th 2026

ReturnsThu, Dec 17th 2026

Nights7

Departing PortPapeete

Ports of CallPapeete, Moorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Dec 11th 2026

ReturnsThu, Dec 17th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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16 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSat, Dec 12th 2026

ReturnsMon, Dec 28th 2026

Nights16

Departing PortOranjestad

Ports of CallOranjestad, Cartagena (2 Days), Bocas Del Toro, San Blas, Panama Canal Daylight Transit, Panama, Balboa, Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Caldera

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 12th 2026

ReturnsSat, Dec 19th 2026

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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8 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSat, Dec 12th 2026

ReturnsSun, Dec 20th 2026

Nights8

Departing PortOranjestad

Ports of CallOranjestad, Cartagena (2 Days), Bocas Del Toro, San Blas, Panama Canal Daylight Transit, Panama, Balboa

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 13th 2026

ReturnsSun, Dec 20th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 13th 2026

ReturnsSun, Dec 27th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 19th 2026

ReturnsSat, Dec 26th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 19th 2026

ReturnsSat, Jan 2nd 2027

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Philipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 19th 2026

ReturnsSat, Dec 26th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 20th 2026

ReturnsSun, Jan 3rd 2027

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 20th 2026

ReturnsSun, Dec 27th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSun, Dec 20th 2026

ReturnsMon, Dec 28th 2026

Nights8

Departing PortBalboa

Ports of CallBalboa, Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Caldera

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 26th 2026

ReturnsSat, Jan 9th 2027

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 26th 2026

ReturnsSat, Jan 2nd 2027

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 26th 2026

ReturnsSat, Jan 2nd 2027

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Philipsburg

On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 27th 2026

ReturnsSun, Jan 3rd 2027

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 27th 2026

ReturnsSun, Jan 10th 2027

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsMon, Dec 28th 2026

ReturnsTue, Jan 5th 2027

Nights8

Departing PortPuerto Caldera

Ports of CallPuerto Caldera (2 Days), Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.