14 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 2nd 2025

ReturnsSun, Nov 16th 2025

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. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, 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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Balcony

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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

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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

ShipStar Pride

DepartsSun, Nov 9th 2025

ReturnsSun, Nov 23rd 2025

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, 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…

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

ShipStar Pride

DepartsSun, Nov 9th 2025

ReturnsSun, Nov 16th 2025

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, 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…

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.

14 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Nov 16th 2025

ReturnsSun, Nov 30th 2025

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. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, 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…

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.

18 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsTue, Nov 18th 2025

ReturnsSat, Dec 6th 2025

Nights18

Departing PortBridgetown

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

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.

11 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsTue, Nov 18th 2025

ReturnsSat, Nov 29th 2025

Nights11

Departing PortBridgetown

Ports of CallBridgetown, 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

Call for pricing

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

ShipStar Pride

DepartsSun, Nov 23rd 2025

ReturnsSun, Dec 7th 2025

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, 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…

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

ShipStar Pride

DepartsSun, Nov 23rd 2025

ReturnsSun, Nov 30th 2025

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, 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…

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.