Windstar Cruises has the surefire cure for the seasonal blues: a tropical cruise. The small ship line has announced 13 different itineraries across the Caribbean and Latin America for the 2026/2027 sailing season. Because the next best thing to being on a trip filled with gorgeous sandy beaches is planning one and looking forward to it.
Windstar’s 26/27 Tropical Season includes the return of many of the line’s most popular itineraries taking place on the 148-guest sailing yacht Wind Star and 312-guest all-suite yacht Star Pride. In addition to returning guest-favorites like the 18-day Star Collector: Reefs & Rainforests and 7-day Costa Rica & Panama Canal, Wind Star also sails a 25-night Southern Caribbean Thanksgiving Jubilee sailing departing November 10, 2026 from Lisbon for an ocean transit to Barbados and cruising among the islands before heading to Colombia and Panama.
Sun lovers are encouraged to book now for the best values and staterooms/suites. Those booking before May 31 receive a complimentary upgrade to All-Inclusive fares, which include Wi-Fi, gratuities, and unlimited select beer, wine, and cocktails, plus $200 onboard credit per stateroom. Additionally, Windstar Cruises’ valued Yacht Club members receive an additional 5 percent off their bookings.
“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.”
Windstar’s Watersports Platform (located on the stern of the ships) is in action on nearly every itinerary in the region (weather/ports allowing) with various complimentary water toys and included gear from kayaks to paddle boards and floating mats for lounging and enjoying the scenery. The tropical cruises also feature Windstar Cruises’ 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 – an UNESCO World Heritage Site, and rum master classes in Martinique.
Contact us for additional information and to plan a small ship cruise with Windstar Cruises.