Windstar Cruises has unveiled its 2026-27 winter itineraries, which prominently feature the Caribbean and Latin America. A standout offering is a unique cruise tour that combines the iconic Machu Picchu experience with a luxurious seven-night voyage through Costa Rica and the Panama Canal.
The cruise offers an optional five-night pre- or post-cruise land package that includes a guided half-day tour of Machu Picchu, a roundtrip Vistadome train ride, and a visit to the historic UNESCO World Heritage Site of Cusco.
Expanded Itineraries in the Caribbean and Latin America
With these newly announced voyages, Windstar Cruises claims to provide the most extensive selection of Caribbean and Latin America itineraries in its history. This expansion also marks the Caribbean debut of the luxurious Star Seeker, which is set to enter service in Europe this December.
From November through March, Windstar will offer a week-long small-ship Caribbean itinerary available from either San Juan or St. Maarten. The brand’s flagship vessel, the Wind Surf, will alternate between two exciting itineraries: the Beach Fun & Sun: A Remote Caribbean Getaway and the Classic Caribbean voyages.
Unique Experiences and Activities
Highlights of these itineraries include exhilarating activities such as snorkeling off the yacht’s marina in Prickly Pear, ziplining through the lush rainforests of St. Kitts, and enjoying sunset rum toasts in Guadeloupe. To enhance guest experience, Windstar is rolling out the AquaBana inflatable dock fleetwide, ensuring easy access to water activities.
From October to January, the Star Pride will offer weekly departures from San Juan, alternating between the San Juan & the Virgin Islands and Windward Islands Surf & Sunsets itineraries.
Latin American Shore Excursions
Before heading to Latin America, the Star Legend will host two sailings from Barbados in November and December 2026. New shore excursion options in the Dominican Republic will include rum tasting experiences in Puerto Plata and a scenic boat tour through the caves and mangroves of Los Haitises National Park in Samana. Guests can also enjoy snorkeling at Horseshoe Reef in the Tobago Cays, along with a French Creole cooking and mixology class led by a local chef in Marigot, St. Martin.
Windstar’s Latin American itineraries will be operated by three of its ships: the Star Legend, Wind Star, and Star Pride, featuring daylight transits of the Panama Canal with engaging narration by onboard experts.
