Windstar Cruises Is Bringing More Ships, New Itineraries, and “AquaBanas” to the Caribbean

There’s a different kind of Caribbean waiting for you—one that’s quieter, more intimate, and defined by the romance of small-ship sailing. On Windstar’s sleek, yacht-style vessels, you don’t just cruise past the islands—you slip into hidden harbors, swim off the back of the ship, and find yourself on beaches where the only footprints in the sand might be your own.

This is Windstar’s take on the Caribbean: a collection of journeys designed around places the big ships can’t reach, paired with the kind of experiences that transform a vacation into a memory you’ll never forget.

More Yachts, More Choices

For winter 2026/2027, Windstar is rolling out its most extensive season yet—35 sailings across 10 itineraries aboard four ships. The highlight: the debut of Star Seeker, a new yacht joining the fleet in the Caribbean. It means more options for travelers, more departures from San Juan and St. Maarten, and more ways to make the Caribbean your own.

Whether you’re sailing on the flagship Wind Surf, alternating between “Beach Fun & Sun” and “Classic Caribbean” itineraries, or stepping onto Star Pride for a voyage through the Virgin Islands or Windward Islands, every itinerary is curated to reveal the diversity of the region.

The Windstar Way

Think you know the Caribbean? Windstar has a way of surprising you. One week you might be snorkeling at Prickly Pear, another zip-lining through St. Kitts’ rainforest, then sipping rum punch at sunset in Guadeloupe. On shore, new excursions range from rum tasting in Puerto Plata to snorkeling Tobago Cays’ Horseshoe Reef to cooking with a local chef in Marigot.

And then there’s Windstar’s Signature Beach Barbecue—set on idyllic stretches in Virgin Gorda or Mayreau—where the sand, the sea, and a sizzling grill become the centerpiece of an unforgettable day.

Life Onboard

Windstar’s ships are built for intimacy: fewer guests, more personal space, and a connection to the water that defines the experience. The Watersports Marina opens directly into the sea, so you can kayak, paddleboard, or swim right off the ship. The newest addition? AquaBanas, private floating platforms that turn the ocean into your own floating lounge.

Every detail feels tailored. There’s no rushing, no long lines, just the ease of traveling as if you’re on a friend’s yacht—if your friend happened to know the best harbors, the hidden reefs, and the islands where authentic culture still thrives.

Beyond the Caribbean

Windstar’s expansion doesn’t stop with island-hopping. Select itineraries include daylight Panama Canal transits, where you can combine sailing with the magic of one of the world’s most iconic landmarks. It’s an invitation to see not only the Caribbean, but also Latin America, in a way that few travelers ever do.