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Windstar's Flagship Sailing Ship
On any day, our 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowl of fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. An Officer’s Suite, which might be the only one of its kind, provides you with the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
Windstar has always been known for our iconic sailing ships, and now we are embarking on a multi-year refresh of the Wind Class ships. The initiative, Setting Sails: A Wind Class Refresh, brings the tight-knit connection of the Windstar community to the forefront through the redesign of public spaces and staterooms. From a revamped lobby to a new pool and larger pool bar, new World Spa by Windstar to a redesigned lounge, this initiative also includes intricate details like new teak decks and décor for a timeless and welcoming experience. Wind Surf will complete her redesign in 2026.
We finished a three week cruise of the Caribbean on the Surf, our 31st cruise with Windstar Cruises on our favorite ship. Needless to say, we like the company and love the ship. The Surf is a beautiful old lady, kept up immaculately and it will be even more beautiful when they redo the cabins soon. What we love: the sails, obviously there are motors but the sails are there, they are up most of the time and they sail, the huge decks to relax on, to read, to hide from the world, for quiet and always breathtaking views, the staff which has been often written up always with how friendly they are and how the service shines, it continues to do so on many levels, the food it is always good but this time it was great, we had the same chef we had in April 2025 and it was 100% delicious at every meal, what is not to love? Ì think WS improved their musical presentations. They had an incredible saxophonist, classically trained, my favorite time of day was listening to him, at the Compass Rose, at sunset watching the sun set behind the clouds and islands what is more beautiful than nature and well played music together? They also had a lady singer and pianist she was very good too. I have been sailing in the Caribbean since I was a teen so I do not think I can judge the islands, love them all, we are in our 70's we go for a vacation, to read, to relax, to be warm for three weeks in January, we are from the NE. We are easy people and what we also love is there is no bling, simple sailing, beauty. We do not need gold trim, circular staircases, Michelin three stars, we love real, natural beauty, and we are loyal. We are grateful for our history with WS. So, my reviews are always positive, that is the way we feel. Is it perfect 24/7, no, what is, nothing? A glorious ship, fabulous crew, great food, engaging ports and interesting and considerate passengers, how much better can a vacation get? PS We think WS has three types of cruises: vacation, 1. the Caribbean is our vacation, 2. trip, to visit places in the world that are different, that interests us etc. 3. Expeditions: Greenland, Alaska and the new Canadian: Québec, and Newfoundland cruises. This classification are all different for everyone. Happy Sailing
My 5th Wind Surf cruise, (of 25+ cruises over the past 30+ years on various ocean and Europe rivers cruise lines). Prior cruises on Surf were 2001-2012, in the Caribbean, Bahamas, and Ireland/Scotland. Some things were better this cruise, some a bit disappointing. Overall, the ship was in spotless condition, with some nicely reconfigured public spaces since I last sailed on her. Verandah was our favorite meals venue, where location, table service, and food variety were nice, as were the servers, but the servers were overworked. Our Candles meal and service were excellent. The open air on-deck big dinner cookout was really fun in spite of the staff's challenge during the set-up cloudburst. Lots of delicious food variety. The private area beach day cookout with music and staff prepared grilled meats was delicious and a lot of fun. Bar service in Compass Rose was generally excellent, but bar service in the Lounge was non-existent at best. Several times we had to go to the bar ourselves to order. Bar service in the Amphora main dining room was spotty, too. (BTW, we're not heavy/demanding drinkers, but we do like an occasional festive on deck sailaway boat drink, and glasses of wine with dinners or during the evening Lounge entertainment). Our deck 2 cabin was clean and well kept as usual, with nice linens. Tender service well done. Saint Bart's 1-hour taxi circuit excursion was unfortunately just a speeding drive by. Sail away on Surf has always been an exhilarating favorite of mine, but on this cruise it seemed only a minor afterthought. Disappointing. This was my cabin mate's first Windstar/Wind Surf experience, partially influenced because I spoke so enthusiastically about my four prior cruises. (She has cruised 52+ times on several lines). She was somewhat disappointed overall. I was a bit embarrassed because it seemed like this cruise didn't live up to what I remembered from my other Wind Surf voyages. But it was still a relaxed, unique experience, and we'd sail on her again. As always, your mileage may vary.
It took a little longer to get this review out but here it is. Back from another great Windstar cruise (our 15th). This time we took a back-to-back Star Collector 12-day cruise (Dec 2nd to 14th) from Philipsburg, Sint Maarten on the recently refurbished Wind Surf. Last time we were on the Surf was in January 2024, pre-renos, so we were excited to get on and see the results for ourselves. I must say the renos look great. The ship looks a lot brighter with lighter colors everywhere; the Yacht Club, Compass Rose, and Amphora all look stylish and contemporary, there is a new jumbo screen in the Lounge (very helpful during Port Talk), new furniture everywhere inside and outside. Very tasteful. Also, the Pool Area redo is very nice (aside from the tacky plastic flowers above the Pool Bar) and the new Marina is a lot of fun but you need to be careful as it can get wobbly with the swells and the soft stairs to get back on can also be difficult to climb. This time we sailed as a couple. All-in-all, a nice relaxing cruise…again Booked this cruise in September during all-in promo. Very good deal. We have done this itinerary several times, but we like these islands and needed a cruise just to relax after a long house building project. We initially booked a B cabin, got upgraded to a nice quiet AX cabin 3.5 weeks prior to cruise. Unlike some prior cruises, we did not travel on a carry-on only as we had a 3-day pre-cruise stay in Anguilla and a 3-day post-cruise stay in Orient Bay St. Martin. We did get the free laundry as this was a Star Collector cruise despite it being only 12 days (normally Star Collector cruises are 14 days and over). As mentioned earlier, while we had been to these islands several times, the only one we did not get off was St Kitts. All other the stops were interesting and we did everything on our own. Nice beach & lunch at Hendo’s Hideout in Jost Van Dyke, some beach and shopping in Soper’s Hole, lots of fun in Titou Gorge in Dominica, great beach BBQ’s in Virgin Gorda and in Mayreau (much nicer spot than previous Pigeon Island). Also a nice albeit expensive day in St Barth with lunch at Pearl Beach Club (St Jean) and some shopping in both St Jean (more local) and Gustavia (more branded). Only had the afternoon in Les Saintes so we walked a bit around town and had a bite to eat at Café de la Marine. Not much to do in town in Nevis aside from visiting Alexander Hamilton’s house or going to one of several beaches on the island although some passengers took a Windstar ATV excursion and thoroughly enjoyed it. We flew in 3 days before and took private ferry from SXM to Blowing Point Anguilla $75 each way p.p, 30 minutes. Rented a car ($50/day incl. insurance with Junies Car rental) and spent 3 nights at La Vue Boutique Inn (great view of Sandy Ground but hotel itself is only average). We have been coming to Anguilla for close to 15 years and it continues to be an uncrowded gem with great beaches and amazing restaurants (try Karaya on Shoal Bay West, (formerly Trattoria Tramonto) now operated by the same owners as Veya, another famous Anguilla eatery). On the day of the cruise, we took same ferry back to SXM and then cab to Port ($30) We arrived at around 1h30pm and boarded rapidly. Met by Captain Matthew Holloway, a glass of bubbly and a cold washcloth, got our picture taken (they no longer take passports away) and went to lunch. Luggage was in the room when we came back from lunch. 240 pax onboard for the first leg (including several who stayed on from the previous ocean crossing) and 300 on the second leg with about 50pax doing back-to-back. Never felt crowded anywhere even at 300. Itinerary/Weather: Weather was beautiful with occasional showers (mostly at night and morning) which did not hinder any activities. Only day with more rain was our 2nd day in St Barth. Temperatures were in the 80’s (27-28C). Seas were relatively calm save for a few breezy days in Les Saintes and St Kitts. We saw very few ships at our different stops, including none in Soper’s Hole, Jost Van Dyke, Virgin Gorda and Mayreau and the ones we saw were mostly small to mid-sized. Busiest was St-Kitts with only 2 other larger ships in town. Deck BBQ’s were held on the night in Jost Van Dyke on the first leg and St Kitts on the second one. Both were excellent Beach BBQ’s were held in Prickly Pear Island in Virgin Gorda and on Mayreau (the beach still nice even following the hurricane). Both sites are very nice and despite Mayreau not having any umbrellas, there was plenty of trees with shade for chairs if needed. Umbrellas were provided on Prickly Pear. Both BBQ’s featured local steel bands playing throughout the lunch. Booking: Booked this cruise 2 ½ months in advance directly with Windstar. Great promotion with All-in package free laundry and $100 ea. in OBC’s. Onboard: As I mentioned earlier, the ship looks very good post drydock. Phase 1 renos included a complete redo of deck 4 which includes Amphora, the Lounge, the Yacht Club, the Star Boutique and the whole pool area (incl. all teak floors at the back of the ship, the ones at the front will undergo same treatment in phase II drydock in late 2026). The furniture on pool deck has just been replaced with more contemporary models (same style as Star Bar/Grill on Star Class ships) with several loungers, sofas and comfy sun beds. The sails were out often throughout the cruise, but less than previous ones. Our Room Attendant Gusti was very good and responsive. We used laundry extensively for everything and had no issues. Left bagful in the morning and all came back following afternoon either on hangers or folded (your choice). No issues with vacuum toilet this time around. We had dinner twice both at Candles and Stella Bistro and we were also invited to join Captain Holloway’s table for dinner on the first week. It was a very entertaining evening, with everyone having interesting stories to tell. Usually had dinner around 7h30-7h45 every night with no issues getting a table for 2. Food is subjective but with Marcelo onboard as chef, quality seemed to have been upped a bit from our previous cruises. Lots of choices incl. tuna, salmon, branzino, rack of lamb, beef Wellington, osso bucco & risotto, veal scaloppini, lobster, Cioppino, great pasta Bolognese and much more. A choice of home baked breads is offered at dinner and changes every night. Food presentation was picture perfect and portions adequate. Not a bad dinner onboard for the both of us. Candles has a somewhat more limited menu but all is very good with perfectly cooked filet mignons (6 or 8 oz), rack of lamb, fish of the day and a great veal chop. Also, great sides of prosciutto parmesan potatoes, asparagus, mushrooms and onion rings and a choice of 5 sauces. Can’t go wrong with that. For breakfast, Veranda can be a bit crowded in the mornings during rush hour (usually 8 to 9) if looking for a table outside but there was always plenty of room inside. Fruit selection at breakfast is decent and a bit better than it was in the past with kiwis, grapefruits and sliced oranges more often but little in the way of berries or mangos. Fresh squeezed OJ was very good. The rest of the buffet is fine with bakery (various sorts of croissants, muffins, breads, bagels and English muffins including some gluten free options), cheeses, smoked salmon/gravlax, yogurt, cereal, oatmeal. No issues with hot items either from buffet (eggs, great bacon, sausage, hash browns) or from the menu including waffles, French toasts (no longer served with real maple syrup however), eggs Benedict as well as omelettes and eggs made to order. The caffe lattes at both the Veranda and Yacht Club (from 6AM) were delicious in the morning. Lunch at Veranda is always less busy than breakfast as lots of guests are out and it’s easy to get a nice table outside. On the menu front, selections continue to improve with several options incl. cold and hot buffet items changing every day, carving and cooking stations (pasta, souvlaki, fajitas etc) plus an à la carte menu which includes a make your own poke bowl, smash burger as well as a fish and a pasta of the day. Always good with a nice glass of rosé (which they had plenty of onboard). New this year is the fact Veranda is open for burgers between 3 and 4pm for those getting back to late. We took advantage of this a few times Yacht Club sandwiches and treats were all delicious in the afternoon when Veranda was closed. Again, we did not use room service. Bars and Entertainment Entertainment included one pianist, a sax player plus a 4-piece band. All were good and there was some dancing in the Lounge as well on a few nights in Compass Rose. There was also some dancing after deck BBQ. Again not much in the way of entertainment around the pool in the afternoon. Cocktails were mostly taken at the pool bar or at Compass Rose. Both Crew Shows in the Lounge were excellent and seemed to be a bit less drawn out than in the past Wine selection is good and the wines included in drink packages (over 30 in total) are decent and varied. We had lots of Provence rosé, California Chardonnay, NZ sauvignon blanc, California Cabs and Zins, as well red Bordeaux and Aussie Shiraz. Sail Aways were always well attended and as mentioned earlier, Captain had sails out more often than not. Went to the bridge every day and had interesting conversations with captain and officers on duty. Marina was open 5 times (excl. beach BBQ days) over the 12 days: Disembarkation Stayed on the ship until 9AM and hopped in a taxi to Orient Bay where we stayed for 3 days post cruise. Orient Bay is a gated community of small hotels and rental units. It has a small village vibe to it with a central courtyard (Place du Village) that has approx. 10 different restaurants and bars that becomes animated at nighttime. Very safe and lots of fun. In the end, a great cruise with many first time Windstar cruisers onboard amazed at the level of personalized service, the great food and the general feeling you were on a yacht and not on a cruise. A totally different experience, 180 degrees from ordinary. We are back on the Surf in March with a group of 17 friends, all newbies to Windstar. They have been hearing me rave about the ships for years, now they will experience it firsthand.
Absolutly great overall experince on the Wind surf. The recent refurb was done very well, the public areas, bars, coffee area all were done very tasteful and impressive for such a small ship. The staff is some of the best on the seas, comparable to the ultra luxury lines. Not much for entertainment but what they did have was very good. Food was very good just short of great, lots of accommodating for dietary needs. The Aft water-sports platform was so much fun! Excursion and tender operations went smoothly. The only real issue we had is the cabin. The Cabins will be refurbished in the next year but currently they are extremely dated, Air Con was struggling to keep up, limited outlets, and an uncomfortable bed. Cabin refurbishment will be very welcome upgrade. Even with this I would still sail again on the windsurf now and again in the future.
Another excellent cruis with Windstar. We had very calm seas most of the cruise. We changed itineraries twice to avoid storms. One night we sailed just under sail. Service was over the top excellent as always on Windstar. Great food, my favorite was the New York steak in Amphora. Dubrovnik was crowded. Cooking with the local family in Dubrovnik was my favorite excursion. Corfu was really beautiful to see. Matt O' is a great entertainment director. The violin player was amazing. Cabin was comfortable and our attendent took great care of us. Snacking at the yacht club every afternoon with fresh pastries and coffee drinks became a routine. Music in the compass rose every night was enjoyable. I enjoyed a Bailys and coffee in the evening. We visited soe ports the big ships could not get to. Nice to not have any lines. We already booked 2 more cruises with Windstar.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowl of fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colours, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
An Officer’s Suite, which might be the only one of its kind, provides you with the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
All Accommodations Feature
World Class Dining Experience
We've upped the onboard dining game with our culinary program, featuring an array of fresh, seasonal ingredients sourced from each port along the journey. Each nightly menu is crafted to highlight the spectacular flavors of the regional cuisine.
At Windstar, we don’t just take you to fascinating destinations, we take you into them, giving you unique access to knowledge and activities that enhance your understanding of the places you visit. Complimentary Destination Discovery Events treat you to iconic experiences that capture the essence of your locale. Guest Lecturers intrigue you with regional topics, adding new dimensions to your voyage. And small group excursions take you to meet locals who are delighted to share their homes, cuisines, and cultures with you.
A day on board your Windstar ship is a day of choices, all of them good. Perhaps you’ll begin with a relaxing massage in World Spa by Windstar. Or maybe an invigorating workout in the Fitness Center. Even better, why not both? After a sumptuous lunch in Veranda, make a splash from the Watersports Platform off the ship’s stern. Everything you can think of for fun in the water is there — swimming, kayaking, and stand-up paddleboarding. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email or order a cheese plate for your stateroom or suite. After dinner, dance to live music in the Lounge. This is your yacht, so of course you’re welcome on the Bridge, where the Captain and officers are delighted to share charts, routes, and vistas with you.
As you prepare for another amazing Windstar day, enjoy a nightcap anywhere you like — on deck, in the Lounge, or why not let us bring it to your suite or stateroom? Your day ends just as it began, blissfully.
Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi.
Please note: Wind Surf does not offer any dedicated children's facilities.
