Windstar Cruises revealed its 2026-27 winter itineraries in the Caribbean and Latin America, featuring a cruise tour that combines Machu Picchu with a seven-night Costa Rica and Panama Canal voyage.
A five-night pre- or post-cruise land package features a half-day guided tour of Machu Picchu, a roundtrip Vistadome train ride and visit to the UNESCO World Heritage Site of Cusco.
With the release of its 2026-27 voyages, Windstar says it now offers the most extensive collection of Caribbean and Latin America itineraries in its history. The expansion includes the Caribbean debut of Star Seeker, a ship entering service in Europe this December.
Any week November through March, Windstar says it will have a weeklong small-ship Caribbean itinerary available from San Juan, St. Maarten or both. The Wind Surf, the brand's flagship sailing ship, will alternate between the seven-night Beach Fun & Sun: A Remote Caribbean Getaway and seven-night Classic Caribbean itineraries.
Highlights are snorkeling off the yacht's marina in Prickly Pear, ziplining through St. Kitts' rainforest and sunset rum toasts in Guadeloupe.
Windstar is rolling out the AquaBana inflatable dock fleetwide. Photo Credit: Windstar Cruises
From October to January, the Star Pride will offer weekly itineraries departing from San Juan, alternating between the seven-night San Juan & the Virgin Islands and seven-night Windward Islands Surf & Sunsets.
Before transitioning to Latin America, the Star Legend will offer two sailings from Barbados in November and December 2026.
New Dominican Republic shore excursions include rum tasting in Puerto Plata and a boat tour to the caves and mangroves of Los Haitises National Park in Samana. Also new: snorkeling at Horseshoe Reef in the Tobago Cays and a French Creole cooking and mixology class led by a local chef in Marigot, St. Martin.
Windstar's Latin American itineraries span three of the line's ships: Star Legend, Wind Star and Star Pride. Daylight transits of the Panama Canal will be narrated by onboard experts.