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. 

The post Escape It or Embrace It: 5 Fabulous Small-Ship Winter Getaways appeared first on Windstar Cruises Travel Blog.

For travelers, a daytime visit to Ephesus is a must-do on any Eastern Mediterranean itinerary that blends Türkiye with the Greek Isles. What if, for one evening, Ephesus would be  your own private corner of ancient Rome? What if you could see it when other visitors don’t have access?

You can.

Where It Started

“Evening in Ephesus,” an atmospheric candlelit dinner exclusively for Windstar guests, was the first of what the line calls its Destination Discovery Events. “Polynesian Feast & Fire” followed — a culinary event and fire-dancing performance on a private motu off Bora Bora that’s since become a signature moment on Tahiti voyages. More recently, Windstar added “Sagas & Songs” to its Iceland itineraries: a cultural evening held at Seyðisfjörður’s iconic Blue Church, blending folk music and Icelandic legend into a gripping account of the island’s heritage.

Windstar’s Destination Discovery events create a connection that changes how travelers experience other cultures, says Elliana Vera, a 25-voyage Windstar guest who’s attended all three and is already planning to return for more.

Elliana Vera, on the way to the Destination Discovery Event on Bora Bora./Jeff Vera

“You feel more like a traveler than a tourist,” Vera says. “You become part of a culture — you’re not just visiting. At that moment, it connects you to something larger than yourself. You’re not simply wandering around, observing. For a passing moment, you become part of a place, and it creates memories that outlast your trip.”

Four New Events for 2027

Destination Discovery has proven popular enough that Windstar is expanding it with four additional events in 2027:

• The Spirit of Croatia — a private, after-hours evening of song and dance in Dubrovnik
• Traditions of Tomonoura — held in a historic village in Japan, featuring a koto performance and traditional tea ceremony
• A Medici Wine Tasting  — live music, cocktails, and Tuscan canapés inside a 16th-century Medici fortress in Livorno, Italy
• The Tower of London at Sunset — a limited-run, after-hours reception offering Windstar guests private access to nine centuries of history

The original Destination Discovery Events continue

Windstar’s original three Destination Discovery events — “Evening in Ephesus” in the Eastern Mediterranean, “Polynesian Feast & Fire” in French Polynesia, and “Sagas & Songs” in Iceland — remain part of the program.

“What inspires us, and what we hope travelers will come away with,” says Kelly Hubbard, Windstar’s director of product development for destinations, “is a sense of awe. To create a sense of being specially welcomed by the people who live here, of being entertained in a way that blends cultures both historic and contemporary.

Ultimately, we hope our travelers feel immersed in a way that sheds light into the cultures of the places they visit.”

The post Destination Discovery Grows: Windstar Adds Japan, Croatia, Italy and London for 2027 appeared first on Windstar Cruises Travel Blog.

What stuck with me most wasn’t the food itself — it was how little distance there was between us and the person making it. Chef Gabriel wasn’t a name on a menu; he was someone you bumped into at the market, traded trekking stories from our visit to Mont-Saint-Michel, or chatted with by the pool. Here’s where that showed up.

Our guest chef

Chef Gabriel Kreuther, a restaurateur in Manhattan who has earned two Michelin stars, was born and raised in France’s Alsace — a nice connection, even though it’s on pretty much the opposite side of the country. Early in the week, I sat in on a cooking demo where he prepared a sea bream with the most incredible green tomato marmalade (later that night, the dish was on every restaurant menu onboard). He didn’t just tell us how to make the marmalade — he shared his farm upbringing, about how at the end of summer his mother needed to find a way to use up the last, often not-quite-ripe, tomatoes. As he wove his family story into the recipe, I was entranced, both by the dish and the storytelling. How often do we get a private audience, as we did on Star Legend, with a James Beard award-winning chef?

The price tag for James Beard activities onboard? Zero.

They’re simply part of the cruise experience. This voyage was the fourth of five onboard partnerships this year; there’s one more to come in October. Does this program offer superb value for the money? You bet. And a PS: Windstar will announce its 2027 lineup in October.

Chef-led voyages also spotlight crew and culinary staff

Guest activities got the spotlight, but the crew benefited too. It was wonderful to learn that the kitchen team and Amphora waitstaff got their own time with him. The onboard chefs cooked his dishes alongside him, while the waitstaff joined tastings so they could speak knowledgeably about his menu with guests. For them, working with a James Beard award-winning chef who’s also earned two Michelin stars was the chance of a lifetime.

The onboard chefs cooked his dishes alongside him, while the waitstaff joined tastings (and sampled dishes) so they could speak knowledgeably about his menu with guests.

Making friends

Speaking of participating, the entire week with Chef Gabriel felt, for me and many others, like making a new friend who just happened to be a superstar chef. I overheard one passenger saying they’d taken a hiking excursion with he and his family, and that he was great to talk with. He, like many of us, complained about a few aches and pains after the trip up towering Mont-Saint-Michel. He joked with us, sat down for quick get-to-know-you conversations, and patiently answered every question we had during and after his cooking demos. My favorite interaction with him was at the Deauville Market, where the Frenchman could identify exotic dishes and explain how they were put together, while Star Legend’s executive chef, Renato, was busy buying fresh ingredients for all of us to try back onboard.

Something to enjoy for every level of culinary enthusiast

You don’t have to be a passionate foodie to have a blast on these chef-hosted cruises. You can pick and choose where you participate. You get to eat really great dishes that you can also make at home (or not — your choice). You can wander off to soak in a hot tub, read a book by the pool, or spend time in port just poking around. The ambience couldn’t have been more relaxed.

And one of the nicest realizations during my first James Beard Foundation-hosted cruise was this: Chef Gabriel’s dishes remain on the menu for future guests to enjoy, alongside selections from previous JBF chefs. It’s an inspiring (and delicious) way to celebrate Windstar’s 11-year partnership and the incredible collection of chefs who have graced its kitchens over the years.

The post Sea Bream, Green Tomatoes, and a New Friend: My Week With James Beard Award-Winning Chef Gabriel Kreuther appeared first on Windstar Cruises Travel Blog.