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10 Night Canary Islands Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsThu, Jan 29th 2026

ReturnsSun, Feb 8th 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.

10 Night Canary Islands Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSun, Feb 8th 2026

ReturnsWed, Feb 18th 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…

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.

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…

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 - Extended Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSun, Dec 14th 2025

ReturnsSun, Dec 28th 2025

Nights14

Departing PortPhilpsburg

Ports of CallPhilpsburg, Falmouth, Road Bay, Sopers Hole, Great Harbour, Jost Van Dyke BVI (2 Days), Gustavia, Philpsburg, Roseau, Mayreau, Terre-de-Haut, Basseterre, 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,…

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.

8 Night European Coast Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsWed, Nov 12th 2025

ReturnsThu, Nov 20th 2025

Nights8

Departing PortLisbon

Ports of CallLisbon, Funchal, Madeira, Santa Cruz de la Palma, San Sebastian, La Gomera, Las Palmas, Gran Canaria, 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…

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, Jan 31st 2026

ReturnsSat, Feb 7th 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…

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 European Coast Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsThu, Aug 13th 2026

ReturnsThu, Aug 20th 2026

Nights7

Departing PortBarcelona

Ports of CallBarcelona, Palma de Mallorca, Spanish Isle, Mahon, Minorca, Calvi, Bastia, Porto Ferraio, 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

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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

DepartsSun, Dec 14th 2025

ReturnsSun, Dec 21st 2025

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

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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 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,…

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 Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSun, Dec 28th 2025

ReturnsSun, Jan 4th 2026

Nights7

Departing PortPhilpsburg

Ports of CallPhilpsburg, Falmouth, 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,…

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 Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSun, Dec 14th 2025

ReturnsSun, Dec 21st 2025

Nights7

Departing PortPhilpsburg

Ports of CallPhilpsburg, Falmouth, 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,…

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 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…

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 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,…

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 Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSun, Dec 28th 2025

ReturnsSun, Jan 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,…

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.

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…

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 Trans-Atlantic Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsTue, Nov 18th 2025

ReturnsTue, Dec 2nd 2025

Nights14

Departing PortLisbon

Ports of CallLisbon, St. John's, 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

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.

13 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 7th 2025

ReturnsSat, Dec 20th 2025

Nights13

Departing PortSan Juan

Ports of CallSan Juan, 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

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…

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.

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…

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.

25 Night Trans-Atlantic Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsTue, Nov 4th 2025

ReturnsSat, Nov 29th 2025

Nights25

Departing PortLisbon

Ports of CallLisbon, Bridgetown, Admiralty Bay, Bequia, Mayreau, St. George's, Kralendijk, Bonaire, Willemstad, Oranjestad, Cartagena, Colon

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

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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 Baltic Sea Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsWed, Jul 15th 2026

ReturnsWed, Jul 22nd 2026

Nights7

Departing PortStockholm

Ports of CallStockholm, Tallinn, Helsinki (2 Days), Ventspils, Gdansk, Ronne + Bornholm, Copenhagen

 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…

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.