Tour of MSY Wind Surf

 “There is nothing, absolutely nothing, half so much worth doing as simply messing about in boats.”
 Kenneth Grahame, The Wind in the Willows

Tour of MSY Wind Surf


We completed this tour of the MSY Wind Surf on the afternoon of Day Two of our transatlantic sailing from Sint Maarten to Lisbon. But in all practicality, our travel journals - and the resulting blog entries - were already overflowing by that point. Rather than bury this beautiful walk-through of our floating home beneath the waves of that day's broader reflections, we’ve chosen to separate it out here.


Wind Surf, Windstar Cruises’ elegant flagship and the world’s largest sailing cruise ship. With five masts, sweeping teak decks, and space for just 342 guests, this elegant vessel offers a rare blend of luxury, intimacy, and old-world charm. We explored every deck during our transatlantic crossing.  From teak-lined decks and sunlit cafés to open-bridge access and starlit dinners, this graceful vessel offers an intimate glimpse into a different kind of voyage - one where slow travel, sea air, and the romance of sailing take centre stage.



In this special entry, we’ll take you on a full tour of the ship, from the pool and promenade to the dining rooms, bars, library, and open bridge.


If you’ve ever dreamed of sailing the high seas in style, here’s what life is really like aboard Wind Surf.

Windstar Cruises and Wind Surf


The MSY Wind Surf is the flagship of Windstar Cruises (the “MSY” stands for Motorized Sailing Yacht) and she’s recently had a thoughtful refresh that keeps this vessel looking elegant and well-loved. At 14,745 gross registered tons, the ship is only about ten percent the size of Cunard’s Queen Mary 2, but that comparison feels almost meaningless. Wind Surf is not a floating city or an ocean liner; she is the largest of Windstar’s sailing yachts, and in fact the largest sailing cruise ship in the world. But to call her a “cruise ship” is to miss the point entirely. She’s a sailing vessel that feels like stepping back into the past and into the golden age of sea travel.


With space for just 342 passengers, spread across 150 staterooms, 18 suites, and 3 deluxe suites, she feels intimate in a way no mega-ship could. The 210 international crew members somehow remember your name after a single meeting, and there’s a relaxed, soothing atmosphere that settles in the moment you step on board. Six decks hold outdoor lounging areas, two whirlpools, and a small swimming pool. Above it all rise her five masts, carrying seven triangular, self-furling sails. Beneath them, four electric generators and two propulsion motors wait for when the wind alone can’t carry us.


Wind Surf is designed so that everything is close at hand. Whether it’s the café for a morning latte, the pool for an afternoon swim, the Compass Rose bar for an evening drink, or the promenade for a stroll, nothing is more than a few steps away. Modern amenities are woven seamlessly into a vessel that feels steeped in the romance of another era. There’s the wind in the sails, the salt in the air, the soft creak of rigging overhead - all of it conspiring to make you forget the chaos of the modern world.

This will be our home for the next fourteen days!

Exploring Wind Surf


We began our walk-around at Reception, the central hub of the ship. Across from the Reception desk sits the Yacht Club Café (which is quickly becoming one of my favourite spaces on board). It’s a bright, welcoming environment where you can get a cappuccino, a fruit smoothie, or a warm croissant at almost any hour. Bowls of fresh fruit are also available along with a tempting assortment of cookies, which are always within reach.

Around the café, the sunlit Reception area opens into a small library. Shelves hold novels in multiple languages, stacks of puzzles, and well-worn board games - a reminder that sometimes the best conversations happen over a game board or puzzle. Behind the café is also the Future Cruises desk, for those already dreaming of their next voyage, and the ship’s store.


Forward from Reception lies the main lounge, which is the ship’s social heart. The main lounge is the place for port talks, evening quizzes, musical performances, and the much-anticipated crew talent show.


Passing through the lounge toward the bow and we arrive at Amphora, the main dining room. Here, most evenings are spent enjoying fine dining that rivals any upscale restaurant ashore. The menu, crafted with input from the James Beard Foundation, changes daily and offers superb vegetarian choices alongside fresh seafood, tender meats, and regional specialties.



Along this same deck, doors and staircases lead out onto the main promenade. With no private balconies on Wind Surf, the promenade is where passengers come for fresh air and sweeping sea views. The teak decking is smooth and warm underfoot, polished by years of use, and lined with classic wooden railings and deep, comfortable lounge chairs. It’s easy to lose hours here, watching the wake unfurl behind us.


Still outdoors, at the aft of Deck 4, we found the pool area including two inviting whirlpools, a small swimming pool, and a pool bar. Above it, on a mezzanine deck, sits the Compass Rose bar. It is becoming a welcoming spot on our voyage in the late afternoons as well as in the golden hour before sunset. Here, passengers drift in to sip cocktails, chat, and listen to live music as the horizon slowly swallowed the sun.


Midship, above Compass Rose on the Star Deck, is the fitness centre. Above that is the ship’s flying bridge, complete with a gleaming wooden wheel which is, in our opinion, a quiet nod to traditional seamanship. 


Moving forward from Compass Rose, we stepped into the Veranda Restaurant. By day, this is a casual indoor-outdoor venue for breakfast and lunch, where the buffet tables offer everything from pastries and fresh fruit to cold cuts, cheeses, and made-to-order smoothies. My personal favourite was the cold-soaked muesli with nuts and fresh berries, enjoyed at a shaded table with nothing but the ocean stretching out in front of me.


At night, Veranda transforms into Candles, a table-service restaurant where dinner is served under the stars. Apparently, it is a favourite restaurant across the fleet, and it’s easy to see why. The menu leans heavily on grilled specialties, and with the James Beard Foundation guiding the culinary program, the food is both refined and deeply satisfying.

Still further forward, Stella Bistro offers an alternative dining possibility featuring an intimate French bistro open on alternating nights. We found the food across the ship to be consistently superb, with daily specials, inventive desserts, and a sense that every dish had been prepared with genuine care.


Near the bow, we reached the Bridge. Wind Surf operates an open-bridge policy, meaning guests are welcome to step in during the day to chat with the officers, learn about navigation, and watch the instruments that guide us across the seas.


Heading back inside, we return to our own stateroom. Our room, like all aboard, has no balcony and instead features two small portholes framed by the ever-changing sea. The décor followed a neutral, timeless palette, with warm wood panelling and soft lighting. A queen-sized bed dominated the space, complemented by a cozy seating area, ample closet storage, and a small but well-designed bathroom.


Each day brought a plate of fresh fruit, and each evening ended with a sweet treat - perhaps a still-warm cookie or a square of fine chocolate. Toiletries from L’Occitane en Provence added a touch of luxury, and a stocked bar fridge meant we were never far from a cold bottle of juice or can of soda if we ever needed it.

Slow Travel by Sea

By the time we completed our loop back to Reception, it was clear how thoughtfully the ship was designed.   Wind Surf is not just a spacious, comfortable, and refined vessel, it is an experience unto itself that invites you to slow down, look outward, and rediscover the joys of travel. With elegant staterooms, world-class dining, open-bridge access, and sweeping teak decks, she offers a truly unique alternative to traditional cruising.


From the soft creak of the rigging to the wind filling the sails, every detail aboard Wind Surf evokes a quieter time - a time when the journey was just as meaningful as the destination.  On Wind Surf, your gaze is always being drawn outward, back to the sails, the sky, and the endless water beyond. She’s not just a way to travel; she’s a way to be present in the world. For us, this means Wind Surf is ideal for our slow travels!

See you out there with your sails up and spirit open to adventure!

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