Caribbean - Windstar Cruises

Small Ship Caribbean Cruises

Let Your Soul Dance

If you could design the perfect island itinerary it would look a lot like these. Ports of call would include tiny towns and hidden harbors known only to private yachts and small ships like ours. Schedules would allow for dropping the Watersports Platform in turquoise bays and raising sails on the way to your next island rendezvous. And the laid-back island vibe would continue on board with a mouthwatering Signature Onboard Barbecue by the pool.

Best of all, on every cruise there would be one day that was even more special than the rest, when you land on a secluded beach for Windstar’s Signature Beach Party, elaborate buffet and watersports included.

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Windstar Knows the Way to the Caribbean

Shh. There are still secret places here that the big ships pass by. Places where there’s only one beach bar in sight, closed if the proprietor decides to go spear fishing. Your Windstar yacht has an uncanny ability to find places like this. Places where your day’s activities are timed by the rumble of your stomach, the drowsiness following a good swim, an iridescent sunset that heralds “sailor’s delight” on the morrow. But then, one glance at your itinerary already told you that.

Find Your Perfect Island Choose from 24 unique Caribbean itineraries ranging from Puerto Rico to Antigua, Cartagena to Barbados. Or, see it all on our 35-day Grand Caribbean & Panamanian Adventure itinerary

Yachtsman's Secrets Visit ports reserved for small ships and private yachts like Mayreau, Bequia, Jost Van Dyke, and Virgin Gorda

Our Specialties Enjoy Windstar’s Signature Beach Party and a Signature Onboard Barbecue on every itinerary - events that are a highlight for our guests. Kayak, paddleboard or enjoy other water toys directly off the complimentary Watersports Platform located at the back of the yacht and your own set of personalized snorkel gear to use throughout your cruise.

Featured Port: Road Bay/Anguilla With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.

Shore Excursion Must-Do: Cooking Caribbean Flavors & Lifestyles (Roseau, Dominica) Today is your opportunity to learn about Dominican cuisine, traditions, and lifestyles at a private home nestled in Roseau’s tropical rainforest. Your hostess will introduce you to the herbs and fresh ingredients on the day’s menu. Then, you can either choose to help prepare a local delicacy, spend your time viewing the mountains or the Caribbean Sea, or stroll the property learning about fruits and spices. End the day by feasting on traditional Caribbean dishes and fruit cocktail blends.