Sarah Bretz, ContributorWindstar Cruises has announced its 2026-2027 Caribbean and Latin America schedule, which includes 13 different itineraries.
Many popular itineraries will return for the 2026-2027 season, taking place aboard the sailing yacht Wind Star and the all-suite yacht Star Pride. In addition to returning guest-favorites like the 18-day Star Collector: Reefs & Rainforests and seven-day Costa Rica & Panama Canal sailings, Wind Star will also operate a 25-night Southern Caribbean Thanksgiving Jubilee voyage departing November 10, 2026 from Lisbon. The cruise will be a transatlantic itinerary to Barbados and other Caribbean islands before heading to Colombia and Panama.
“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,” says Jess Peterson, Windstar’s director of destination experience and itinerary planning. “A small-ship Caribbean cruise is a totally different experience.”
The Watersports Platform, located on the stern of Windstar’s ships, will be in action on nearly every itinerary in the region — weather and ports permitting. It offers guests free access to various water toys and gear including kayaks, paddle boards, and floating mats. These sailings also include Windstar’s signature deck and beach barbecue experiences.
All Caribbean and Latin American cruises offer an array of curated shore excursions that range from lounging at iconic beach clubs (like the Le Barthélemy Resort and Spa) to a more active selection of snorkeling adventures, deep sea fishing, jungle hikes to waterfalls, and even sailing America’s Cup Race sailboats in St. Maarten.
Cultural outings, such as visiting the Embera Indigenous Tribe in Panama allow cruisers to immerse more deeply in the region with a special connection to local life. Additional guest favorites include foodie walking tours in Bequia, cruising to the Pitons in St. Lucia, and rum master classes in Martinique.
Early Booking Offer
Those who book one of these newly-announced sailings before May 31, 2025 will receive a complimentary upgrade to All-Inclusive fares. This includes wifi; gratuities; unlimited beer, wine, and cocktails; and a $200 onboard credit per stateroom. Windstar’s Yacht Club members will also receive a five percent savings on their bookings.
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