Windstar Unveils 2026/2027 Caribbean and Latin America Voyages

August 27, 2025 at 09:00 AM EDT

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

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.

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Wind Surf sails in the Caribbean, near Jost van Dyke

“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 travelers more yachts, more choices, and more opportunities for winter getaways.

Caribbean Your Way

Think you know the Caribbean? Think again. Any week November through March, Windstar has a weeklong 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 through March, Wind Surf, the brand's flagship sailing ship, will alternate between the 7-night Beach Fun & Sun: A Remote Caribbean Getaway and 7-night Classic Caribbean itineraries to reveal just how diverse and dazzling the region can be. Imagine snorkeling 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 itineraries departing from San Juan, alternating between the 7-night San Juan & the Virgin Islands and 7-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, snorkeling 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 7-night Costa Rica & Panama Canal itinerary. The 5-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-favorite onboard Star Pride that unfolds with vivid contrasts: the remote & 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 colorful 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 colorful 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 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 in Peru, 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. Learn more about our Star Collector series here.

Need to Know

New! Pay Now, Save More: Save 5% with booking code PIF when you pay in full at the time of booking.
Early Booking Offer: Reserve by October 31 to take advantage of the best fares we will ever offer for these voyages — and enjoy up to $200 in onboard credit and an All-Inclusive experience (ALL In package with comp gratuities, Wi-fi, select alcohol) worth $99/day per person.
Best Suite Selection: Booking early ensures access to the most desirable suites.
Contact: To plan a small ship cruise with Windstar book online here, contact a travel advisor, reach out to Windstar Cruises by phone at 866-258-7245, or request a call by a Windstar vacation planner.

Images Here with credit to Windstar Cruises.

About Windstar Cruises:

For four decades, Windstar Cruises has been reimagining small-ship cruising with a distinctive blend of relaxed luxury and genuine connection to the world’s most captivating destinations. From its origins with motor sailing yachts tailored for upscale yet casual travel, Windstar has grown into a diverse fleet of three Star Class all-suite yachts and three Wind Class sailing yachts, offering voyages that are both intimate and inspiring. Two highly anticipated new yachts, Star Seeker and Star Explorer, set to debut in December 2025 and 2026, expand the fleet to eight yachts accommodating 150-350 guests. Windstar’s legendary Wind Class sailing yachts are also undergoing a meticulous two-phase redesign to be completed by 2027. Windstar yachts sail to more than 330 ports across Europe, the Caribbean, Costa Rica and the Panama Canal, Alaska, Canada and New England, Japan, the South Pacific, and Asia. Unlike most cruise lines, Windstar sails year-round in the Mediterranean and Tahiti, offering different destination experiences seasonally. Each Windstar voyage is designed to immerse guests in authentic cultural experiences, all while delivering the comfort, service, and style that define the Windstar difference.

Windstar Cruises is proud to be part of the Xanterra Travel Collection®, a distinguished group of global hospitality and travel companies with a legacy spanning over a hundred years. Xanterra operates iconic national parks, including Grand Canyon, Yellowstone, Glacier, and Death Valley. The Xanterra Travel Collection® is owned by The Anschutz Corporation, the ultimate owner of the Broadmoor, Sea Island, and entertainment giant AEG, Anschutz Entertainment Group.