Windstar Cruises has announced its most extensive collection of Caribbean and Latin America itineraries for the 2026/2027 season, which includes 35 sailings across 10 different itineraries on four yacht-style ships. This growth is partly due to the debut of Star Seeker in the Caribbean during winter 2026.
“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, in a press statement. “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.”
Windstar Weeks
The Caribbean offers weeklong itineraries available from November through March, departing from San Juan or St. Maarten. These voyages showcase both popular destinations and lesser-known ports that larger ships can’t access, such as Anguilla and Jost Van Dyke. Of note are Windstar’s signature beach barbecue experiences in Virgin Gorda and Mayreau.
Wind Surf, the company’s flagship sailing vessel, will alternate between two 7-night itineraries from December to March. The Beach Fun & Sun: A Remote Caribbean Getaway and Classic Caribbean routes offer contrasting experiences, from snorkeling off the yacht’s marina in Prickly Pear to zip-lining through St. Kitts’ rainforest.
Star Pride will operate weekly departures from San Juan between October and January, alternating between the San Juan & the Virgin Islands and Windward Islands Surf & Sunsets itineraries. Star Legend joins the Caribbean lineup with two sailings from Barbados in November and December 2026 before transitioning to Latin American routes.
Your clients will enjoy new shore excursions that enhance these Caribbean voyages, including rum tasting in Puerto Plata, exploring Haitises National Park in Samana, snorkeling at Horseshoe Reef in the Tobago Cays and participating in a French Creole cooking class in Marigot.
In Latin America, Windstar introduces a cruise tour combining Machu Picchu with its 7-night Costa Rica & Panama Canal itinerary. This 5-night pre- or post-cruise package features guided tours of Machu Picchu and Cusco, including a Vistadome train ride to the ancient Incan site.
The Panama Canal remains a highlight, with daylight transits narrated by onboard experts. The Panama Canal, Cartagena, San Blas Islands & More itinerary on Star Pride offers a blend of experiences, from the pristine beaches of San Blas Islands to the historic streets of Cartagena.
Costa Rica-focused voyages aboard Star Legend or Star Pride allow guests to explore Manuel Antonio National Park’s diverse ecosystems and enjoy catamaran sails along the Gold Coast’s Playa Flamingo.
For those seeking extended journeys, Windstar offers 22 Star Collector voyages on eight different itineraries. These longer sailings, such as the new 16-night Latin American Explorer and the 70-night Grand Star Collector from Istanbul to Costa Rica, provide more sea days and deeper cultural immersion.
Savings Available
Windstar is offering early booking incentives, including a 5 percent discount with the Pay Now, Save More option using the booking code PIF. Reservations made by Oct. 31 will receive up to $200 in onboard credit and an All-Inclusive package worth $99 per person per day. Early bookings also ensure access to the most desirable suites.
For more information, visit windstarcruises.com.
