Small Ship Caribbean Cruises
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.
WINDSTAR VOYAGES TO THE CARIBBEAN
Pick your perfect Caribbean itinerary — and get ready to absorb picturesque beaches stretching into the sunset.
Star Collector: Caribbean Explorations
James Beard Foundation: Beach Fun & Sun: A Remote Caribbean Getaway
Star Collector: Wind Spirit Grand Caribbean Adventure 2026
Classic Caribbean
Star Collector: Costa Rica, Panama & Aruba
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Classic Caribbean
Star Collector: Caribbean Collection: ABC, BVI & the Windwards
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Star Collector: Antilles Adventures
Star Collector: Blue Seas of the Windward Islands
Beach Fun & Sun: A Remote Caribbean Getaway
Star Collector: Caribbean Islands & Colombian Coast Discovery
Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal
Star Collector: Central American Explorations via the Panama Canal
Star Collector: Deep Dive into the Blue: Underwater Worlds of the Caribbean
Star Collector: Blue Seas of the Windward Islands
Star Collector: Rainforest Refuges of Panama & Costa Rica via the Panama Canal
Star Collector: Leeward & Windward Caribbean Havens
Star Collector: Windward Islands & Spanish New World
Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores
Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama
Lush & Lovely Islands of the Lesser Antilles
Star Collector: A Lesser Antilles Odyssey
Star Collector: Windward Islands, Spanish Cities & Costa Rica
Star Collector: Windward Islands, ABC Islands & the Virgin Island
Star Collector: Coffee, Canal & Callaloo: Central America, Columbia & the Caribbean
Star Collector: Captivating Caribbean
