This winter, escape it or embrace it; Either way, a small ship can get you there. Think warm-water classics like the Caribbean, the Panama Canal and Costa Rica, or island-hopping through Southeast Asia and the Canary Islands. Then there are the outliers: French Polynesia and Tahiti, where Windstar sails year-round through tropical waters, and the Mediterranean, our new favorite way to spend the season, minus the summer crowds.
Here’s where you can go and what you can see in winter with Windstar:
Caribbean
When it’s best: Late October through mid-Mar
Our ships: Star Pride, Star Legend, Wind Surf, Wind Star (operates just one Caribbean sailing before repositioning to Costa Rica and the Panama Canal).
What we love: The variety. Every island is different — an experience in Aruba is light years from St. Barts, and they’re both fabulous. With three ships in the region this winter, you can choose a quick seven-night getaway focused on the British Virgin Islands; a cosmopolitan, French-influenced route with calls at Martinique, St. Barts and St. Martin; or a fun-in-the-sun itinerary through southern islands like Bequia, Curaçao and Barbados. One often-overlooked draw of the region: local cuisine blending fresh-caught seafood with African, Amerindian, European, Chinese and East Asian influences.
Details: Explore Windstar’s 20-plus Caribbean cruise options for winter travel.
Costa Rica and the Panama Canal
When it’s best: Late November–late January
Our ships: Wind Star and Star Legend
What we love: Stories of the Panama Canal’s construction and operation are legendary, and it remains a marvel of engineering. Voyages typically spend one day transiting the canal and the rest of the voyage in tropical Panama and Costa Rica, experiencing beaches, watersports, jungle adventures, horseback riding and small villages.
What isn’t as well known, as Windstar contributing writer Melinda Crow reports, is how much time is spent in Costa Rica itself: “I loved that on our Panama Canal cruise, the majority of our active days would be in Costa Rica, with rainforest tours, dolphin-watching boat rides and even an afternoon on Windstar’s floating marina set up at the stern of the ship.
“We continued south into Panama for a relaxing day on the beach with Windstar’s Signature Beach Barbecue, before our final excursion, an educational visit to the Emberá, an Indigenous Panamanian tribe critical to protecting the environment and the rivers feeding into the canal.”
Among the highlights: volcanoes (and the coffee plantations that thrive in volcanic soil), biodiversity ranging from marine life to butterflies, and ziplines — particularly at the Monteverde Cloud Forest Reserve.
Details: Itineraries focused on Panama, the Panama Canal and Costa Rica range from standard week-long voyages to Star Collector trips that combine multiple routes. You can even add a Monteverde Cloud Forest and Arenal Volcano land excursion. Some Caribbean itineraries also incorporate Panama and Costa Rica.
French Polynesia
When it’s best: Windstar sails from its Tahiti homeport year-round, but the region has real seasonality. Northern Hemisphere travelers visiting during their winter will find it warmer and drier, with tropical downpours rather than all-day rain — and landscapes at their lushest and most spectacular. Snorkelers will appreciate the warm waters, and since November–March is low season, the islands see fewer visitors.
Our ships: Star Breeze is based in Tahiti year-round; Wind Star joins it there beginning in March 2027, also year-round.
What we love: It’s always comfortably tropical in French Polynesia, making it an easy escape from winter weather — and what a place to escape to. Black- and white-sand beaches, serene blue-green lagoons, tropical fish and colorful coral beds define the coastline, while mountain trails offer hikes with views over volcanic valleys. The appeal extends beyond natural beauty to a vibrant culture and warm local hospitality. And Windstar’s exclusive Destination Discovery Event — a sunset barbecue with fire dancing on a motu off Bora Bora — is a highlight of every voyage.
Details: Learn more about cruising French Polynesia year-round here.
Southeast Asia
When it’s best: Windstar’s first Southeast Asia season in several years — focused on Vietnam, Thailand, Malaysia, Cambodia and Singapore — runs November through March.
Our ship: Star Seeker
What we love: Step into a watercolor scene: longtail boats drifting past the karst pillars of Halong Bay, water buffalo tilling verdant rice paddies, and Thai islands hand-picked from more than 1,400 to choose from — the ones worth the detour. Other itineraries move on to glimmering neon cities. Southeast Asia is a region where the food tells its own story: Peranakan fusion in Malaysia and Singapore, Khmer noodles in Cambodia. Overnight stays in Hong Kong, Hanoi, Ho Chi Minh City and Singapore mean real time in the night markets — not just a rushed shore excursion. And history anchors it all: Hoi An’s Ancient Town, where 18th-century merchant houses still stand.
Details: In Southeast Asia, travel options are built around core voyages, with extended Star Collector trips and land-based adventures also available.
Canary Islands
When it’s best: The Canary Islands are an archipelago of seven islands that are part of Spain (cruises also call at Portugal’s Madeira). A subtropical region just off the coast of Africa, the Canaries are delightful year-round, but Windstar’s November–January itineraries offer a great escape from winter.
Our ship: Wind Spirit
What we love: “There’s a reason they call these islands Europe’s Hawaii,” says Windstar president Chris Prelog. “From black-sand beaches to cities with Spanish and Portuguese influences, it always felt to me like it was everything you could want in a vacation destination.”
Most voyages homeport from lush Tenerife, with ports of call including the stark, almost moon-like Lanzarote; the volcanic San Sebastián de La Gomera; and Santa Cruz, on the island of La Palma, with its Spanish colonial history. On Fuerteventura, Puerto del Rosario is known for Corralejo Natural Park, a massive golden dune field meeting crystal-clear water. Madeira is the only Portuguese island on these itineraries.
A new addition to Windstar’s ports of call this winter is El Hierro. A UNESCO Biosphere Reserve with more than 100 plant and animal species, it’s considered Europe’s Galápagos.
Details: Windstar operates itineraries in the region from November through January.
The Mediterranean’s Locals Season
When it’s best: It’s not necessarily best in winter or summer — it depends on your preferences. In winter, summer stalwarts like Santorini, St. Tropez, Portofino, Split and Kotor step back, and cosmopolitan cities such as Florence, Nice and Genoa — typically more crowded in warm weather — step in. Some cities, like Venice, Dubrovnik, Athens, Rome and Barcelona, are fabulous year-round. “Sunshine in the Mediterranean doesn’t take a holiday in the winter,” says Janet Bava, Windstar’s chief commercial officer, who first proposed the line’s year-round Mediterranean cruises three years ago. She’s right.
These itineraries run January–March (2026) and November–March (2027).
Our ships: Windstar’s new Star Explorer debuts in late December this year and stays in the region through winter 2027–2028, when it will be joined by Star Legend.
What we love: Ships spend more time in port during winter’s “locals” itineraries, including overnights and later departures. Weather can be unexpectedly pleasant, with temperatures in the 60s (read our guide on tips for enjoying a winter cruise in the Mediterranean). Itineraries focus on larger cosmopolitan cities like Nice, Naples, Genoa and Dubrovnik during locals season, a time when they belong not to tourists but to the people who live there — an energy that’s quieter and stiller, yet still bustling and lively.
Details: To see all the options, from Venice to Rome’s Civitavecchia, Barcelona and more, go here.
