Windstar Cruises has revealed a wave of new Caribbean and Latin America itineraries for the 2026/27 season ahead of the launch of Star Seeker later this year

The release of the new voyages sees Windstar offer its largest-ever collection of Caribbean and Latin America experiences, offering 35 sailings across ten itineraries, operated across four yacht-style ships.

New highlights include daylight Panama Canal transits, first-time shore excursions, and new tours to Machu Picchu.

Michele Hanson, product development manager at Windstar Cruises, said: ““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.”

Hanson added that guests can also enjoy unspoiled beaches in the Grenadines, and the French and Creole culture of Guadeloupe. Their watersports marina also gives clients the chance to kayak, paddle-board, swim, or simply relax.

Earlier this year, Windstar announced plans to expand its UK footprint by appointing a global commercial director to oversee a new dedicated London office.

Explore the Caribbean

Between November and March, Windstar will offer week-long Caribbean itineraries from San Juan and San Maarten. Clients can enjoy extensive use of the line’s marina platform in the British Virgin Islands, visit smaller ports like Anguilla and Jost Van Dyke, and participate in a beach barbecue in Virgin Gorda and Mayreau in the Grenadines.

From December 2026 through March 2027, Wind Surf, the brand’s flagship sailing ship, will alternate between two seven-night itineraries. New shore excursions include rum tasting in Puerto Plata, boat trips to Haitises National Park’s mangroves in Samana, snorkelling in the Tobago Cays, and a French Creole cooking class in Marigot.

Meanwhile, Windstar Cruises’ Latin American itineraries will offer a new blend of both sea and land experiences. Some of the pre and post cruise packages include includes guided tours of Machu Picchu, a Vistadome train ride, and a visit to Cusco.

Windstar’s Latin American voyages will be offered on three ships: Star Legend, Wind Star, and Star Pride. On the Naturally Costa Rica voyage, clients can also experience close encounters with wildlife – colourful endemic birds, sloths, and unique flora. Additionally, the 2026/2027 season introduces 22 Star Collector voyages across eight itineraries.

These longer sailings, such as the 16-night Latin American Explorer and the 70-night Grand Star Collector from Istanbul to Costa Rica, combine multiple itineraries, more sea days into one journey.