Windstar expands Caribbean ’26/’27 season

A record number of sailings are featured in Windstar Cruises’ Caribbean and Latin America deployment for northern hemisphere winter 2026/2027, with the season to mark the debut of Star Seeker.

The cruise line revealed 35 new sailings across 10 itineraries on four yacht-style ships, with the milestone expansion including first-time shore excursions and a new Cruise Tour that will visit Machu Picchu.

“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,” Product Development Manager Michele Hanson said. 

“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.”

Windstar’s “Caribbean Your Way” program offers weekly seven-night sailings between November and March from San Juan and St. Maarten. Highlights include exclusive access to ports like Anguilla and Jost Van Dyke, plus Windstar’s Signature Beach Barbecue on Virgin Gorda and Mayreau in the Grenadines.

From December through March, flagship Wind Surf alternates between two unique itineraries: Beach Fun & Sun: A Remote Caribbean Getaway and Classic Caribbean. Meanwhile, Star Pride departs weekly from San Juan with itineraries such as San Juan & the Virgin Islands and Windward Islands Surf & Sunsets.

In Latin America, a new Cruise Tour will launch combining a seven-night Costa Rica & Panama Canal sailing with a five-night land package to Machu Picchu, including a guided tour, Vistadome train ride and visit to Cusco.

Meanwhile, Star Legend, Wind Star, and Star Pride will offer daylight Panama Canal transits narrated by onboard experts “in what feels like a river cruise for the day.”

Windstar also introduces 22 Star Collector voyages – longer, immersive journeys such as the 70-night Grand Star Collector from Istanbul to Costa Rica. These include complimentary laundry and added sea days for deeper cultural experiences.

Guests booking by 31 October will receive up to US$200 onboard credit and Windstar’s ‘ALL In’ package.