Windstar Cruises has announced 35 sailings on 10 different itineraries across four yacht-style ships in the Caribbean and Latin America for winter 2026/27, including daylight Panama Canal transits, first-time shore excursions and new cruise tours to Machu Picchu.
With the release of new 2026 and 2027 voyages, Windstar now offers the most extensive collection of Caribbean and Latin America itineraries in its history. The expansion includes the debut of Star Seeker, sailing in the Caribbean during winter 2026, giving travelers more yachts, more choices, and more opportunities for winter getaways.
From November through March, Windstar offers a weeklong small-ship Caribbean itinerary from San Juan, San Maarten, or both. Guests can indulge in extensive use of Windstar’s Marina platform in the BVIs, sail into tiny ports that big ships skip—like Anguilla and Jost Van Dyke—and enjoy Windstar’s Signature Beach Barbecue in Virgin Gorda and Mayreau in the Grenadines.
From December through March, 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 to reveal just how diverse and dazzling the region can be. Imagine snorkeling off the yacht’s marina in Prickly Pear, zip-lining through St. Kitts’ rainforest or enjoying rum-soaked sunset toasts in Guadeloupe.
From October to January, Star Pride offers 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, Star Legend will offer two sailings from Barbados in November and December 2026.
Windstar has also added new Caribbean shore excursions. Guests can enjoy rum tasting in Puerto Plata, explore the caves and mangroves of Haitises National Park in Samana by boat, go snorkeling at Horseshoe Reef in the Tobago Cays and cook like a local with a French Creole cooking and mixology class led by a local chef in Marigot.
Windstar’s Latin American itineraries span three of the line’s ships: Star Legend, Wind Star and Star Pride. The Panama Canal is brought to life with daylight transits narrated by onboard experts in what feels like a river cruise for the day. Returning this season is “Panama Canal, Cartagena, San Blas Islands & More,” a guest-favorite onboard Star Pride. Guests can snorkel in crystal-clear waters with giant manta rays, paddle alongside dolphins or relax at a Signature Beach Barbecue on a secluded stretch of sand.
Windstar offers a cruise tour package that combines Machu Picchu with its seven-night “Costa Rica & Panama Canal” itinerary. The five-night pre- or post-cruise package features a half-day guided tour of the ancient, terraced landscape, roundtrip Vistadome train ride and visit to the UNESCO World Heritage Site of Cusco.
On “Naturally Costa Rica” voyages aboard Star Legend or Star Pride, guests can explore Manuel Antonio National Park, where the jungle is alive with colorful birds, sloths and playful capuchin monkeys. They can glide through winding mangroves on a guided boat tour, and set sail on a catamaran along the Gold Coast’s Playa Flamingo.
Within the new 2026/27 season, there are also 22 Star Collector voyages on eight different itineraries. These voyages combine multiple itineraries into one seamless journey—like the new 16-night “Latin American Explorer” itinerary and 70-night “Grand Star Collector” from Istanbul to Costa Rica. These longer sailings offer more days at sea, complimentary laundry and deeper cultural immersion.
Travelers can save 5 percent with booking code “PIF” when they pay in full at the time of booking. Reserve by October 31 to take advantage of the best fares and enjoy up to $200 in onboard credit and an All-Inclusive experience (ALL In package with comp gratuities, Wi-fi, select alcohol) worth $99/day per person.
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