special offer
 

Cruise Planners® Exclusive:
5% discount on most sailings
+ Up to $300 shipboard credit per stateroom on select sailings

 

 

Dreams of Tahiti

7 Nights | Star Breeze | September 10, 2026 | Roundtrip Papeete

Moorea, Raiatea (overnight), Motu Mahaea, Bora Bora (overnight), Huahine

Balcony Suite from $7,471

 

Connect to the World

Now with even more late-night departures, overnights in ports, and Concierge Collection shore excursions, Windstar guests can connect to the wonder, authenticity, and majesty of a world discovered by small yacht.

Jump in for Fun

A cruise to Tahiti, the Mediterranean or the Caribbean isn’t just about the land. It’s about the sea. That warm, turquoise water is more than willing to answer your question about what to do today, and the phenomenal Watersports Platform on the stern of your Windstar yacht is more than willing to provide the means.

Immerse Yourself in Regional Culture

Local guides share insight into their everyday world, as well as insider highlights that you don’t want to miss. As part of a smaller group, you’re able to bypass long lines, visit places off the beaten path, and get all of your questions personally answered.

 

8 Night European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Explorer

DepartsFri, Jan 22nd 2027

ReturnsSat, Jan 30th 2027

Nights8

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Naples, Messina, Dubrovnik (2 Days), Zadar, Venice (2 Days)

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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, Jan 23rd 2027

ReturnsSat, Feb 6th 2027

Nights14

Departing PortPhilipsburg

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

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Balcony

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Suite

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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 European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Explorer

DepartsSat, Jan 30th 2027

ReturnsSun, Feb 7th 2027

Nights8

Departing PortVenice

Ports of CallVenice (2 Days), Zadar, Dubrovnik (2 Days), Messina, Naples, Civitavecchia (Rome)

Inside Cabin

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Outside

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Balcony

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Suite

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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 European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Explorer

DepartsSat, Jan 30th 2027

ReturnsSun, Feb 14th 2027

Nights15

Departing PortVenice

Ports of CallVenice (2 Days), Zadar, Dubrovnik (2 Days), Messina, Naples, Civitavecchia (Rome), Livorno (Florence,Pisa) (2 Days), Genoa, Nice (2 Days), Barcelona (2 Days)

Inside Cabin

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Outside

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Balcony

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Suite

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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, Jan 30th 2027

ReturnsSat, Feb 13th 2027

Nights14

Departing PortPhilipsburg

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

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

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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, Jan 30th 2027

ReturnsSat, Feb 6th 2027

Nights7

Departing PortPhilipsburg

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

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 6th 2027

ReturnsSat, Feb 13th 2027

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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,…

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 6th 2027

ReturnsSat, Feb 20th 2027

Nights14

Departing PortPhilipsburg

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

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Explorer

DepartsSun, Feb 7th 2027

ReturnsSun, Feb 14th 2027

Nights7

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Livorno (Florence,Pisa) (2 Days), Genoa, Nice (2 Days), Barcelona (2 Days)

Inside Cabin

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Outside

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Balcony

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Suite

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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 Explorer

DepartsSun, Feb 7th 2027

ReturnsTue, Feb 23rd 2027

Nights16

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Livorno (Florence,Pisa) (2 Days), Genoa, Nice (2 Days), Barcelona (2 Days), Valencia, Cartagena, Gibraltar, Malaga (2 Days), Palma de Mallorca, Spanish Isle, Barcelona

Inside Cabin

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Outside

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Balcony

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Suite

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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 Explorer

DepartsSun, Feb 14th 2027

ReturnsTue, Feb 23rd 2027

Nights9

Departing PortBarcelona

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

Inside Cabin

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Outside

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Balcony

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Suite

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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 20th 2027

ReturnsSat, Feb 27th 2027

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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,…

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

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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 20th 2027

ReturnsSat, Mar 6th 2027

Nights14

Departing PortPhilipsburg

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

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 Explorer

DepartsTue, Feb 23rd 2027

ReturnsThu, Mar 11th 2027

Nights16

Departing PortBarcelona

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

Inside Cabin

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Outside

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Balcony

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Suite

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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 Explorer

DepartsTue, Feb 23rd 2027

ReturnsThu, Mar 4th 2027

Nights9

Departing PortBarcelona

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

Inside Cabin

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Outside

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Balcony

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Suite

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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 27th 2027

ReturnsSat, Mar 6th 2027

Nights7

Departing PortPhilipsburg

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

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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, Feb 27th 2027

ReturnsSat, Mar 13th 2027

Nights14

Departing PortPhilipsburg

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

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 6th 2027

ReturnsSat, Mar 13th 2027

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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,…

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 6th 2027

ReturnsSat, Mar 20th 2027

Nights14

Departing PortPhilipsburg

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

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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 13th 2027

ReturnsSat, Mar 20th 2027

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,…

Inside Cabin

Call for pricing

Outside

Call for pricing

Balcony

Call for pricing

Suite

Call for pricing

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