Small Ship Caribbean Cruises

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.

With its protected shoreline, calm surf, spectacular coral reefs, and sugar-soft beaches, Road Bay has become a destination for boaters, eager to visit its delightful restaurants, bars, and shops.

Visit ports reserved for small ships and private yachts like Mayreau, Bequia, Jost Van Dyke, and Virgin Gorda.

Kayak, paddleboard or swim directly off the complimentary Marina Platform located at the back of the yacht, and enjoy your own set of personalized snorkel gear to use throughout your cruise.

Enjoy Windstar’s Signature Beach Party and a Signature Onboard Barbecue on every itinerary — events that are always a highlight for our guests.

Experience the Caribbean in Windstar Style

Select your perfect voyage from over a dozen Star Collectors, or explore Windstar's over 20 unique Caribbean itineraries ranging from Puerto Rico to Antigua, Cartagena to Barbados. Then again, why choose just one? You can see it all on our month-long Grand Caribbean & Panamanian Adventure.

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.

With its protected shoreline, calm surf, spectacular coral reefs, and sugar-soft beaches, Road Bay has become a destination for boaters, eager to visit its delightful restaurants, bars, and shops.

Visit ports reserved for small ships and private yachts like Mayreau, Bequia, Jost Van Dyke, and Virgin Gorda.

Kayak, paddleboard or swim directly off the complimentary Marina Platform located at the back of the yacht, and enjoy your own set of personalized snorkel gear to use throughout your cruise.

Enjoy Windstar’s Signature Beach Party and a Signature Onboard Barbecue on every itinerary — events that are always a highlight for our guests.

Get Closer to the Caribbean

The perfect island itinerary would look a lot like these. Ports of call would include tiny towns and hidden harbors known only to small ships and private yachts like ours. Schedules would allow for dropping the Marina Platform in cerulean seas and raising sails on the way to your next island rendezvous. And the laid-back island vibe continues on board with a mouthwatering Signature Onboard Barbecue. Best of all, every sailing includes a landing on a secluded beach for Windstar’s Signature Beach Party, elaborate buffet, and watersports included.

Yachtsman's Secrets

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.

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