Windstar Cruises has announced its 2026-27 Caribbean and Latin America sailing season, featuring 13 itineraries.

Sailings include returning favorites like the 18-day Star Collector: Reefs and Rainforests and the seven-day Costa Rica and Panama Canal on the Wind Star and Star Pride yachts.

The season also features a 25-night Southern Caribbean Thanksgiving Jubilee cruise, departing November 10, 2026, from Lisbon to Barbados, with stops in Colombia and Panama.

Guests booking by May 31 can enjoy a complimentary upgrade to All-Inclusive fares, which cover Wi-Fi, gratuities, select drinks, and a $200 onboard credit. Yacht Club members will receive an additional 5 percent discount.

“Windstar embraces a laid-back, yachting vibe in the Caribbean. We focus on relaxing beaches and the more exclusive islands like Jost Van Dyke, St. Barths, and Virgin Gorda. We layer on our signature experiences like a beach barbeque on a remote island and swimming from the ship’s stern platform,” said Jess Peterson, Windstar’s director of destination experience and itinerary planning. “A small-ship Caribbean cruise is a totally different experience.”  

Windstar’s Watersports Platform will be available on nearly every itinerary in the region with various complimentary water toys and gear, from kayaks to paddle boards and floating mats. The tropical cruises also feature Windstar Cruises’ signature deck and beach barbecue experiences. 

Travelers can also look forward to a range of shore excursions, from lounging at beach clubs (like the Le Barthélemy Resort and Spa) to snorkeling adventures, deep sea fishing, jungle hikes to waterfalls and sailing America’s Cup Race sailboats in St. Maarten. Guests can also enjoy cultural outings like visiting the Embera Indigenous Tribe in Panama, food tours in Bequia, exploring the Pitons in St. Lucia and attending rum master classes in Martinique.