Windstar Unveils Biggest Caribbean Latin America Season 2026 27

Windstar Cruises has announced an expanded program for winter 2026-27, offering the most extensive deployment of Caribbean and Latin America itineraries in the company's history. Featuring 35 sailings across 10 itineraries on four yacht-style ships, the season includes exclusive journeys, daylight Panama Canal transits, first-time excursions, and immersive Cruise Tours to destinations such as Machu Picchu. The debut of the new ship Star Seeker in the Caribbean, along with innovative land and sea experiences, underscores Windstar’s commitment to redefining small-ship cruising.

Overview of the Winter 2026-27 Program

The expanded season runs from October 2026 through March 2027, emphasizing access to lesser-visited islands, scenic coastal gems, and small-ship marina facilities. Core itineraries combine seven-night voyages with extended options, catering to travelers seeking unique cultural and nature-focused experiences. Highlights include stops at iconic Caribbean destinations like Virgin Gorda and Mayreau for the exclusive Signature Beach Barbecue, and calls to Anguilla and Jost Van Dyke.

Ships and Itineraries

• Wind Surf: The flagship sailing yacht will alternate between two seven-night itineraries, Beach Fun & Sun: A Remote Caribbean Getaway and Classic Caribbean, from December 2026 through March 2027. Featured activities include snorkeling at Prickly Pear, zip-lining through St. Kitts rainforest, and sunset toasts in Guadeloupe.
• Star Pride: From October 2026 through January 2027, this vessel will offer weekly itineraries from San Juan, alternating between San Juan & the Virgin Islands and Windward Islands Surf & Sunsets.
• Star Legend: Available for select Barbados-based sailings in November and December 2026 before transitioning to Latin America for nature-rich itineraries that include Panama Canal transits.
• Star Seeker: Making its debut in the Caribbean for winter 2026-27, bringing new choices for small-ship explorations in peak season.

Exciting New Shore Excursions

Windstar is expanding its repertoire of shore excursions across the Caribbean and Latin America, blending cultural immersion, cuisine, and nature adventures:

• Rum tasting experiences in Puerto Plata.
• Boat explorations of Haitises National Park’s caves and mangroves in Samaná.
• Snorkeling at Horseshoe Reef.
• French Creole cooking classes in Marigot.

Guests in Costa Rica will have opportunities to hike through cloud forests, enjoy natural hot springs near Arenal Volcano, sail along Playa Flamingo's Gold Coast, and explore the wildlife-rich environments of Manuel Antonio National Park.

Cruise Tours: Machu Picchu and Beyond

The season also introduces a new Machu Picchu Cruise Tour, combining a seven-night Costa Rica & Panama Canal sailing with a land-based adventure to Peru’s famous Incan ruins. The tour includes guided exploration of Machu Picchu, round-trip Vistadome train rides, and visits to UNESCO World Heritage sites such as Cusco. This unique offering captures mountain landscapes, Andean heritage, and vibrant coastal experiences in one seamless journey.

Panama Canal and Expanded Collector Voyages

Latin America itineraries offer narrated daylight transits of the Panama Canal onboard Star Legend, Wind Surf, and Star Pride. Signature voyages such as Panama Canal, Cartagena, San Blas Islands & More integrate scenic canal crossings with wildlife encounters, beach barbecues, snorkeling, and other eco-friendly activities.

For travelers seeking extended adventures, Windstar’s 22 Star Collector itineraries combine routes into back-to-back journeys. Standout options include the 16-night Latin American Explorer and the 70-night Grand Star Collector voyage from Istanbul to Costa Rica.

Booking Incentives and Promotions

Windstar is offering travelers opportunities to save and enjoy additional perks:

• Guests using booking code PIF can save 5% on fares by paying in full at the time of booking.
• Reservations made by October 31, 2023, will receive up to $200 in onboard credit.
• An optional all-inclusive package, priced at $99 per person per day, offers added convenience with bundled dining, beverages, and Wi-Fi.

Travelers are encouraged to book early to secure preferred stateroom categories and excursion spots, as availability may vary by sailing.

Frequently Asked Questions (FAQs)

What new shore excursions are available in the Caribbean and Latin America?

In addition to classic outings, Windstar’s winter 2026-27 season introduces rum tasting in Puerto Plata, cave and mangrove tours in Haitises National Park (Samaná), snorkeling at Horseshoe Reef, and French Creole cooking classes in Marigot.

What makes the Machu Picchu Cruise Tour distinctive?

The Cruise Tour combines land and sea experiences, featuring a seven-night Costa Rica & Panama Canal sailing paired with guided visits to Machu Picchu. It includes roundtrip rides on the Vistadome train and time in Cusco to explore UNESCO World Heritage landmarks and Incan historic sites.

Do Windstar’s Latin America sailings include daylight Panama Canal transits?

Yes, select itineraries feature narrated daytime Panama Canal crossings. Onboard experts provide commentary to enhance guests’ understanding of the canal’s history, engineering, and ecosystem.

What ships are part of Windstar’s winter 2026-27 program?

The program will feature four yacht-style ships, Wind Surf, Star Pride, Star Legend, and Star Seeker, with the latter making its Caribbean debut during this season.

What booking incentives are available for these sailings?

Guests paying in full at booking with code PIF can enjoy a 5% discount. Reservations made by October 31, 2023, are eligible for up to $200 in onboard credit, while an all-inclusive package priced at $99 per person per day can also be added.