Windstar Cruises Unveils 2026/27 Caribbean & Latin America Voyages

Windstar Cruises has revealed its 2026/27 Caribbean and Latin America lineup, comprising 35 sailings on 10 different itineraries across four ships, including the Star Seeker’s Caribbean debut, daylight Panama Canal transits, first-time shore excursions, and new cruise/tours to Machu Picchu.

The collection of sailings is the line’s most extensive ever in the region.

“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,” said Michele Hanson, product development manager at Windstar Cruises.

Caribbean Windstar’s Way

From November through March, Windstar will offer weeklong itineraries from San Juan, St. Maarten, or both. Highlights will include stops at islands such as Anguilla and Jost Van Dyke, along with Windstar’s Signature beach barbecue in Virgin Gorda and Mayreau, in the Grenadines.

From December through March, Wind Surf will alternate between the seven-night Beach Fun & Sun and seven-day Classic Caribbean itineraries. Alternatively, from October to January, Star Pride will sail weekly from San Juan, alternating between the seven-night San Juan & the Virgin Islands and seven-night Windward Islands Surf & Sunsets itineraries.

Before re-positioning to Latin America, Star Legend will offer two sailings from Barbados in November and December, 2026, as well.

New Caribbean shore excursions take clients rum tasting in Puerto Plata, by boat to the caves and mangroves of Haitises National Park in Samana, snorkeling at Horseshoe Reef in the Tobago Cays, and cooking like a local with a French Creole cooking and mixology class led by a local chef in Marigot.   

Windstar in Latin America

For the first time, Windstar will offer a cruise/tour that combines Machu Picchu with its classic seven-night Costa Rica & Panama Canal itinerary. The five-might pre- or post-package features a half-day guided tour of the site, roundtrip Vistadome train ride, and a visit to the UNESCO World Heritage Site of Cusco.

On the water, Windstar’s Latin America lineup spans three of the line’s ships and several itineraries including the popular Panama Canal, Cartagena, San Blas Islands & More itinerary onboard Star Pride. Both Star Pride and Star Legend also offer the Naturally Costa Rica itinerary.

Star Collector Voyages

Within the 2026/27 season, there are also 22 Star Collector voyages on eight different itineraries. Each Star Collector Voyage combines multiple itineraries into one journey—like the new 16-night Latin American Explorer itinerary and 70-night Grand Star Collector from Istanbul to Costa Rica.