Windstar Cruises unveils Caribbean and Latin America voyages for winter 2026-27

Windstar Cruises has launched a collection of 35 sailings across 10 different itineraries in the Caribbean and Latin America for the winter 2026-2027 season.

In its most extensive collection in the region, the luxury line will have four yacht-style ships, including the debut of Star Seeker, offering a range of voyages.

Every week between November 2026 and March 2027, the small-ship operator will offer a seven-night Caribbean itinerary from San Juan, Sint Maarten or both.

Wind Surf, the flagship of the fleet, will alternate between a seven-night Beach Fun & Sun: A Remote Caribbean Getaway and a seven-night Classic Caribbean itinerary, between December 2026 and March 2027.

Star Pride will operate weekly sailings from San Juan, either the San Juan & the Virgin Islands or the seven-night Windwards Islands Surf & Sunsets itineraries, between October 2026 and January 2027.

Star Legend will sail two voyages from Barbados in November and December 2026, before transitioning to Latin America.

In a first for the line, Windstar Cruises is offering the option for a five-night pre or post-cruise package featuring a half-day guided tour to Machu Picchu, roundtrip Vistadome train ride and visit to Cusco for selected Latin American cruises.

Star Pride will operate the returning itinerary of Panama Canal, Cartagena, San Blas Islands & More, while Star Legend and Star Pride will sail Naturally Costa Rica voyages.

There will be 22 Star Collector voyages on eight different itineraries in the new season which combine multiple itineraries into one journey, such as the 16-night Latin American Explorer and the 70-night Grand Star Collector from Istanbul to Costa Rica.

Prices for Caribbean voyages start from £1,977 per person for a seven-night Classic Caribbean voyage on Wind Surf sailing on January 23, 2027.

Fares for Latin America voyages lead in at £1,761 per person for the eight-night Naturally Costa Rica voyage on Star Legend departing on December 20, 2026.

Agents can save their clients 5% using the booking code “PIF” when paying in full at the time of booking.

There is also an early booking offer in place until October 31 offering up to $200 in onboard credit and a package with complimentary gratuities, Wi-Fi and select alcohol worth £74 per person per day.

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.

“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.”