Windstar unveils 2026/2027 Caribbean season
Windstar Cruises just unveiled its Caribbean and Latin America program for winter 2026/27.
It features 35 sailings on 10 different itineraries across four yacht-style ships, including daylight Panama Canal transits, plus first-time shore excursions and new Cruise Tours to Machu Picchu.
“Windstar offers a more intimate take on the Caribbean, visiting smaller islands 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.
The new 2026 and 2027 voyages offers the most extensive collection of Caribbean and Latin America itineraries in the line’s history.
The expansion includes the debut of Star Seeker, sailing in the Caribbean during winter 2026.
Any week November through March, Windstar has a week-long small-ship Caribbean itinerary available from San Juan, San Maarten or both.
It includes small ports like Anguilla and Jost Van Dyke plus Windstar’s signature beach barbecue in Virgin Gorda and Mayreau in the Grenadines.
From December 2026 through March 2027, Wind Surf, the brand’s flagship sailing ship, will alternate between the seven-night Beach Fun & Sun: A Remote Caribbean Getaway and seven-night Classic Caribbean itineraries.
From October to January, Star Pride offers weekly sailings departing from San Juan, alternating between the seven-night San Juan & the Virgin Islands and seven-night Windward Islands Surf & Sunsets itineraries.
Before transitioning to Latin America, Star Legend will offer two sailings from Barbados in November and December 2026.
The big highlight in Windstar’s Latin America itineraries is a cruise tour that combines Machu Picchu with its classic seven-night Costa Rica & Panama Canal itinerary.
The five-night pre- or post-cruise package features a half-day guided tour and roundtrip Vistadome train ride and visit to the UNESCO World Heritage Site of Cusco.
Windstar’s Latin American itineraries span three of the line’s ships: Star Legend, Wind Star and Star Pride.
There are transits of the Panama Canal with the Panama Canal, Cartagena, San Blas Islands & More itinerary onboard Star Pride.
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Learn more about : Windstar Cruises ( N. America )
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Editor for TravelMole North America and Asia pacific regions. Ray is a highly experienced (15+ years) skilled journalist and editor predominantly in travel, hospitality and lifestyle working with a huge number of major market-leading brands. He has also cover in-depth news, interviews and features in general business, finance, tech and geopolitical issues for a select few major news outlets and publishers.
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