The Wind & Stars know the Way! Caribbean Escape 2025

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Get away from the crowd and journey to unique destinations aboard Windstar’s intimate small ships. Sail away to the sun-soaked islands of the Caribbean for a unique tropical retreat with Windstar Cruises.

Sail away on Windstar Cruises, 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep.

Go off the beaten path and visit less frequented spots like Les Saintes and Roseau Walk the grounds where pirates and Spanish explorers once roamed with dreams of gold and treasure. Shower in a cool crystal-clear waterfall in the heart of a dense rainforest.
 

Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.

Itinerary

  1. Caribbean Escape 2025

    Experience Philipsburg, St. Maarten, Roseau, Dominica, Pigeon Island, St. Lucia, Les Saintes, Guadeloupe,Port of Basseterre, St. Kitts from $3,349!

    Caribbean Escape 2025

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