Windstar Cruises has announced 35 sailings across 10 different itineraries for winter 2026/2027, marking the cruise line's most extensive collection of Caribbean and Latin America itineraries to date. The program will deploy four yacht-style ships across the regions and introduce new shore excursions and cruise tour packages.
The expansion includes the debut of Star Seeker in the Caribbean during winter 2026, providing additional capacity for the cruise line's small-ship Caribbean offerings. From November through March, Windstar will operate weekly Caribbean itineraries departing from San Juan, Puerto Rico, and San Maarten, or both ports.
"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," said Michele Hanson, product development manager at Windstar Cruises. "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."
The Caribbean program features varied deployment across the fleet. Wind Surf will alternate between seven-night "Beach Fun & Sun: A Remote Caribbean Getaway" and seven-night "Classic Caribbean" itineraries from December 2026 through March 2027. Star Pride will offer weekly departures from San Juan, alternating between seven-night "San Juan & the Virgin Islands" and seven-night "Windward Islands Surf & Sunsets" itineraries from October 2026 to January 2027. Star Legend will operate two Barbados departures in November and December 2026 before transitioning to Latin America.
New Caribbean shore excursions include rum tasting in Puerto Plata, Dominican Republic; boat excursions to caves and mangroves in Haitises National Park in Samana, Dominican Republic; snorkeling at Horseshoe Reef in the Tobago Cays in the Grenadines; and French Creole cooking and mixology classes with local chefs in Marigot, Saint Martin.
The Latin America program introduces the significant addition of a new cruise tour combining Machu Picchu, Peru, with the seven-night "Costa Rica & Panama Canal" itinerary. The nine-night pre- or post-cruise package includes a half-day guided tour of Machu Picchu, roundtrip Vistadome train transportation and visits to the UNESCO World Heritage Site of Cusco.
Latin American itineraries will operate across three ships: Star Legend, Wind Star and Star Pride. The program features daylight Panama Canal transits with onboard expert narration. Returning itineraries include "Panama Canal, Cartagena, San Blas Islands & More" onboard Star Pride and "Naturally Costa Rica" voyages on Star Legend or Star Pride.
Additional pre- and post-cruise land packages are available for Costa Rica, featuring activities such as hiking through cloud forests, visiting natural hot springs near Arenal Volcano and wildlife spotting excursions.
The 2026/2027 season also includes 22 Star Collector voyages across eight different itineraries, combining multiple itineraries into longer seamless journeys. These include a new 16-night "Latin American Explorer" itinerary and a 70-night "Grand Star Collector" trip from Istanbul to Costa Rica; the latter features additional sea days, complimentary laundry service and extended cultural immersion opportunities.
Editor’s Note: This article was generated by AI, based on a press release distributed by Windstar Cruises. It was fact-checked and reviewed by a TravelAge West editor.
