Windstar Unveils 2026/2027 Caribbean & Latin America Voyages

With fleet expansion, Windstar now has more sailings open to book in the Caribbean & Latin America than ever before.

Windstar Cruises today announced 35 sailings on 10 different itineraries across four yacht-style ships in the Caribbean and Latin America for Winter 2026/2027, including daylight Panama Canal transits, first-time shore excursions and new Cruise Tours to Machu Picchu.

“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. “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.”

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 travellers more yachts, more choices and more opportunities for winter getaways.

Caribbean Your Way
Any week November through March, Windstar has a week-long small-ship Caribbean itinerary available from San Juan, San Maarten or both. Guests can indulge in extensive use of Windstar’s iconic marina platform in the BVIs, sail into tiny ports that big ships skip – like Anguilla and Jost Van Dyke – and experience a taste of Windstar’s signature beach barbecue in Virgin Gorda and Mayreau in the Grenadines.

And with Windstar, no two sailings are alike:

• From December 2026 through March 2027,Wind Surf, the brand’s flagship sailing ship, will alternate between the seven-night Beach Fun & Sun: A Remote Caribbean Getaway and a seven-night Classic Caribbean itineraries to reveal just how diverse and dazzling the region can be. Imagine snorkelling 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 sailings 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.

New Caribbean shore excursions take you rum tasting in Puerto Plata, by boat to the caves and mangroves of Haitises National Park in Samana, snorkelling at Horseshoe Reef in the Tobago Cays and cooking like a local with a French Creole cooking and mixology class led by a local chef in Marigot.

Latin America Unlocked
Perhaps the biggest news in Windstar’s Latin America itineraries lies beyond the sea with a cruise tour that combines Machu Picchu with its classic 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.

Back on the water, 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 favourite onboard Star Pride that unfolds with vivid contrasts: the remote and pristine beaches and rich indigenous culture of San Blas Islands; Cartagena, a UNESCO World Heritage Site surrounded by 400-year-old walls; and Bocas del Toro, where colourful seaside villages open into coral reefs, mangroves and a rainforest alive with red frogs and sloths. 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.

On Naturally Costa Rica voyages aboard Star Legend or Star Pride, guests wander among the Jurassic landscapes of Manuel Antonio National Park, where dense jungle is alive with flashes of colourful birds, sloths and playful capuchin monkeys; glide through winding mangroves on a guided boat tour and set sail on a catamaran along the Gold Coast’s Playa Flamingo – each moment offering an intimate look at Costa Rica’s untamed beauty.

Diving in on Land
Pre and post-cruise land tours let guests make the most of their time. Before or after their voyage, guests can deepen the adventure by hiking through Costa Rica’s emerald-green cloud forests, soaking in natural hot springs near Arenal Volcano or spotting toucans and monkeys among cascading jungle waterfalls. At Machu Picchu, guests can stand in the shadows of Incan temples and watch morning mist rise over the Andes. Each pre- or post-cruise experience offers a rich, cinematic backdrop to Windstar’s tropical escapes

A Taste of Both
Within the new 2026/2027 season, there are also 22 Star Collector voyages on eight different itineraries. For those who want to experience it all, Star Collector 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.

Need to Know

• 2026/2027 Caribbean prices start from £1,977 per person for the seven-night Classic Caribbean voyage on Wind Surf departing 23^rd January 2027.
• 2027/2027 Latin America prices start from £1,761 per person for the eight-night Naturally Costa Rica voyage on Star Legend departing 20^th December 2026.
• New! Pay Now, Save More: Save 5% with booking code PIF when you pay in full at the time of booking.
• Early Booking Offer: Book by 31^st October 2025 to take advantage of the best fares for these voyages and enjoy up to $200 in onboard credit and an All-In package with complimentary gratuities, Wi-fi and select alcohol worth £74 per person per day.
• Best Suite Selection: Booking early ensures access to the most desirable suites.

To plan a small ship cruise with Windstar, book through Windstar Cruises’ UK General Sales Agent on 0800 008 6682. For more details https://www.windstarcruises.co.uk/booking-in-the-uk/.  For more information visit www.windstarcruises.co.uk