Windstar Cruises Unveils 2026-27 Winter Itineraries in the Caribbean, Latin America

Windstar Cruises will offer 10 different itineraries in the Caribbean and Latin America during the winter of 2026-27—the most extensive collection of itineraries in the region in the company’s history.

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

In total, guests will be able to choose between 35 sailings on four ships, including Windstar’s new ship Star Seeker. The company will offer a variety of week-long sailings in the Caribbean, with stops at destinations like Anguilla, Jost Van Dyke, Virgin Gorda, Mayreau, St. Kitt, Guadeloupe and beyond.

New Caribbean shore excursions include rum-tastings in Puerto Plata, boat tours of the caves and mangroves of Haitises National Park in Samana, snorkeling at Horseshoe Reef in the Tobago Cays and French Creole cooking and mixology classes led by a local chef in Marigot.   

In Latin America, guests can explore the Panama Canal during daylight transits narrated by onboard experts, as well as visits to destinations like the San Blas Islands, Manuel Antonio National Park and Bocas del Toro.

Windstar will also offer a cruise tour that combines Machu Picchu with its 7-night “Costa Rica & Panama Canal” itinerary. The 5-night pre- or post-cruise package features a half-day guided tour of Machu Picchu, a roundtrip Vistadome train ride and visit to the UNESCO World Heritage Site of Cusco. 

Guests can also book one of 22 Star Collector voyages, which combine multiple itineraries into one seamless journey. 

Guests who book by October 31 can take advantage of Windstar’s early booking offer, which includes discounted fares, up to $200 in onboard credits and the line’s all-inclusive package. Travelers can also save 5 percent when they pay in full at the time of booking using the code PIF.

This article, describing some of Windstar Cruises’ 2026-27 Itineraries, originally appeared in TravelPulse.

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