Windstar unveils 2026/2027 Caribbean and Latin America Voyages 

Windstar Cruises will be offering 35 sailings on 10 different itineraries across four yacht-style ships in the Caribbean and Latin America for Winter 2026-2027, including daylight Panama Canal transits, first-time shore excursions and new Cruise Tours to Machu Picchu.

Michele Hanson, product development manager at Windstar Cruises, said: “Windstar offers a quieter, more intimate take on the Caribbean, visiting smaller islands that larger ships can’t access — from the unspoiled beaches and coral reefs of the Grenadines to the French flair and Creole culture of Guadeloupe.”

And Hanson added: “Guests also love our Watersports Marina, which opens frequently in the Caribbean and lets you dive right in—whether it’s kayaking, paddleboarding, swimming, or just relaxing on a float.”

With the release of new 2026 and 2027 voyages, Windstar now offers the most extensive collection of Caribbean and Latin America itineraries in its history. The expansion includes the debut of Star Seeker, sailing in the Caribbean during winter 2026, giving travellers more yachts, more choices, and more opportunities for winter getaways.

From November through March, Windstar has a weeklong small-ship Caribbean itinerary available from San Juan, San Maarten, or both. Guests can indulge in extensive use of Windstar’s iconic Marina platform in the BVIs, sail into tiny ports that big ships skip — like Anguilla and Jost Van Dyke and experience a taste of Windstar’s Signature Beach Barbecue in Virgin Gorda and Mayreau in the Grenadines.

And with Windstar, no two sailings are alike:

• From December through March, Wind Surf, the brand’s flagship sailing ship, will alternate between the 7-night Beach Fun & Sun: A Remote Caribbean Getaway and 7-night Classic Caribbean itineraries to reveal just how diverse and dazzling the region can be. Imagine snorkeling off the yacht’s marina in Prickly Pear, zip-lining through St. Kitts’ rainforest, or enjoying rum-soaked sunset toasts in Guadeloupe.
• From October to January, Star Pride offers weekly itineraries departing from San Juan, alternating between the 7-night San Juan & the Virgin Islands and 7-night Windward Islands Surf & Sunsets
• Before transitioning to Latin America, Star Legend will offer two sailings from Barbados in November and December 2026.

Sail on over to www.windstarcruises.com for more.