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10 Night Canary Islands Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsWed, Feb 18th 2026

ReturnsSat, Feb 28th 2026

Nights10

Departing PortSanta Cruz de Tenerife

Ports of CallSanta Cruz de Tenerife, San Sebastian, La Gomera, Santa Cruz de la Palma, Funchal, Madeira (2 Days), Lanzarote, Las Palmas, Gran Canaria (2 Days), Santa Cruz de Tenerife

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 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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Ocean View

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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, 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,…

Inside Cabin

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Ocean View

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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 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…

Inside Cabin

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Ocean View

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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, Mar 21st 2026

ReturnsSat, Mar 28th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charleston, 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

Call for pricing

Ocean View

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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 - Extended Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 21st 2026

ReturnsSat, Apr 4th 2026

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Charleston, 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,…

Inside Cabin

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Ocean View

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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.

19 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsTue, Nov 18th 2025

ReturnsSun, Dec 7th 2025

Nights19

Departing PortLisbon

Ports of CallLisbon, Philipsburg, 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

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Ocean View

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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

DepartsSun, Dec 14th 2025

ReturnsSun, Dec 28th 2025

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, Charleston, 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

Ocean View

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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.

21 Night Trans-Atlantic Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Mar 28th 2026

ReturnsSat, Apr 18th 2026

Nights21

Departing PortPhilipsburg

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

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

Ocean View

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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 Trans-Atlantic Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Mar 28th 2026

ReturnsSun, Apr 12th 2026

Nights15

Departing PortBridgetown

Ports of CallBridgetown, Lisbon

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…

Inside Cabin

Call for pricing

Ocean View

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.

25 Night Trans-Atlantic Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsSat, Mar 28th 2026

ReturnsWed, Apr 22nd 2026

Nights25

Departing PortBridgetown

Ports of CallBridgetown, Lisbon, Tangier, Malaga (2 Days), Cartagena, Valencia, Palma de Mallorca, Spanish Isle, Tarragona, Barcelona

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…

Inside Cabin

Call for pricing

Ocean View

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 Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Jul 4th 2026

ReturnsSat, Jul 11th 2026

Nights7

Departing PortAthens (Piraeus)

Ports of CallAthens (Piraeus), Mykonos, Kusadasi, Patmos, Santorini, Monemvasia, Nafplion, Athens (Piraeus)

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…

Inside Cabin

Call for pricing

Ocean View

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.

17 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsTue, Jul 7th 2026

ReturnsFri, Jul 24th 2026

Nights17

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Amalfi, Vibo Valentina, Reggio Calabria, Taranto, Otranto, Rab, Venice, Rovinj, Zadar, Hvar, Dubrovnik (2 Days), Kotor, Koper, Venice

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

Ocean View

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.

8 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsTue, Jul 7th 2026

ReturnsWed, Jul 15th 2026

Nights8

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Amalfi, Vibo Valentina, Reggio Calabria, Taranto, Otranto, Rab, Venice

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

Ocean View

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 Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Jul 11th 2026

ReturnsSat, Jul 18th 2026

Nights7

Departing PortAthens (Piraeus)

Ports of CallAthens (Piraeus), Mykonos, Kusadasi, Patmos, Santorini, Monemvasia, Nafplion, Athens (Piraeus)

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…

Inside Cabin

Call for pricing

Ocean View

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.

9 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsWed, Jul 15th 2026

ReturnsFri, Jul 24th 2026

Nights9

Departing PortVenice

Ports of CallVenice, Rovinj, Zadar, Hvar, Dubrovnik (2 Days), Kotor, Koper, Venice

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

Ocean View

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 Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsThu, Jul 16th 2026

ReturnsThu, Jul 23rd 2026

Nights7

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Ponza Island, Amalfi, Lipari, Scenic cruising Stromboli, Porto Rotondo, Sardinia, Porto Vecchio, Corsica, Civitavecchia (Rome)

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…

Inside Cabin

Call for pricing

Ocean View

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.

8 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsFri, Jul 24th 2026

ReturnsSat, Aug 1st 2026

Nights8

Departing PortVenice

Ports of CallVenice, Rovinj, Split, Dubrovnik, Kotor, Giardini Di Naxos, Sorrento, Civitavecchia (Rome)

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

Ocean View

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 European Coast Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsFri, Jul 24th 2026

ReturnsSun, Aug 9th 2026

Nights16

Departing PortVenice

Ports of CallVenice, Rovinj, Split, Dubrovnik, Kotor, Giardini Di Naxos, Sorrento, Civitavecchia (Rome), Amalfi, Vibo Valentina, Reggio Calabria, Taranto, Otranto, Rab, Venice

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

Ocean View

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 Mediterranean Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Jul 25th 2026

ReturnsSat, Aug 1st 2026

Nights7

Departing PortAthens (Piraeus)

Ports of CallAthens (Piraeus), Mykonos, Kusadasi, Patmos, Santorini, Monemvasia, Nafplion, Athens (Piraeus)

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…

Inside Cabin

Call for pricing

Ocean View

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.