Windstar Cruises has unveiled its most extensive schedule to date in the Caribbean and Latin America, announcing 35 sailings across ten itineraries for the 2026–2027 winter season. The program will be operated by four of the line’s small-ship yachts and includes daylight transits of the Panama Canal, first-time excursions, and new land-based extensions such as tours to Machu Picchu.
The deployment coincides with the arrival of Star Seeker, which will debut in the Caribbean in late 2026. The addition provides the company with increased capacity and a broader range of options for winter cruising.
From November through March, Windstar vessels will sail weeklong itineraries from San Juan and St. Maarten, visiting smaller ports typically inaccessible to larger ships. The flagship Wind Surf will alternate between two seven-night routes, one focused on remote islands and beaches, the other highlighting classic Caribbean destinations. Star Pride will operate alternating weeklong itineraries from San Juan, while Star Legend will offer departures from Barbados in late 2026 before repositioning to Latin America.
The new program introduces additional Caribbean excursions, including rum tastings in Puerto Plata, guided boat tours through the mangroves and caves of Haitises National Park in Samaná, snorkeling at Horseshoe Reef in the Tobago Cays, and a Creole cooking and mixology class in Marigot.
In Latin America, Windstar will expand its presence with itineraries aboard Star Legend, Wind Star, and Star Pride. The line will continue to feature daylight transits of the Panama Canal with commentary from onboard experts. Guest-favorite sailings include itineraries combining Cartagena and the San Blas Islands with Bocas del Toro, while Costa Rica-focused voyages highlight national parks, mangrove tours, and coastal catamaran sailing.
The company has also introduced a land program linking Machu Picchu with its Costa Rica and Panama Canal sailings. The pre- or post-cruise package includes guided exploration of the archaeological site, a Vistadome train journey, and a visit to Cusco. Additional overland options include excursions in Costa Rica’s cloud forests, hot springs near Arenal Volcano, and jungle waterfall hikes.
For extended travel, Windstar will offer 22 Star Collector voyages across eight itineraries, combining multiple routes into longer sailings. Among these is a 16-night Latin American Explorer and a 70-night Grand Star Collector voyage from Istanbul to Costa Rica, both designed to provide deeper immersion and extended time at sea.
With this deployment, Windstar positions itself to deliver its broadest collection of warm-weather voyages to date, balancing small-port accessibility in the Caribbean with expanded offerings in Latin America.