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Wind Surf Cruise Review
4.0 / 5.0
Cruise Critic Editor Rating
241 Reviews

Great Yachtsman’s Caribbean Cruise

Wind Surf Cruise Review by Misty Morning

14 people found this helpful
Trip Details
  • Sail Date: Mar 2020
  • Destination: the Caribbean
  • Cabin Type: Deluxe Oceanview Stateroom

I am writing this as I go through my mandatory quarantine following another great cruise on the Wind Surf (the last one before operations were halted). This was our second Windstar cruise in less than 4 months after having done a 14-day BTB Caribbean cruise with some friends on Star Legend in November. This time we were travelling as a couple and met 2 other couples from our hometown of Montreal on the ship during the trip. We flew in same day from Montreal as there was a direct flight to Sint-Maarten that arrived around 12h30 giving us plenty of time for our scheduled 7pm departure. We are in our mid 50's and this was our 9th Windstar cruise (all in the Caribbean) and 4th on the Windsurf. We also sailed 5 times with Celebrity prior to switching to Windstar in 2013. This was again a great cruise although there were a few hiccups along the way (especially with the tender operations). We continue to enjoy Windstar's small ships despite the fact capacity was increased by 32 pax on the Wind Surf's recent dry dock (more on this later but we did not feel the increase was noticeable). What we enjoy is the fact you can do things independently easily (we only took one snorkeling excursion from the ship), there is a relaxed dress code at dinner, the food is excellent and last but not least the great service staff who go out of their way to make your cruise memorable. This was the 3rd time we did Yachtsman’s Caribbean itinerary as we love all the stops along the way (BVI's, St Barth, Antigua) although the reason we chose this particular one is the fact it had a twist with no sea day and an extra stop on our favorite island, Anguilla. The weather was a bit challenging during our first 2 stops (Tortola and Jost Van Dyke) with gray skies, strong winds and regular showers. Although weather had begun to clear when in JVD, Captain decided to cancel Virgin Gorda and Beach BBQ in Fischer's Cove and instead go back to Road Town and spend the night docked and remain there the following day. This was disappointing for people that wanted to see the Baths. The crossing from Road Town to Anguilla was very rocky with several guest not able to sleep (incl. myself). The rest of the week was calmer and much sunnier. Another great but not perfect cruise with Windstar


We booked 45 days in advance (we always go for lowest priced cabin as location is not necessarily important to us). We called the company directly (we did not use a travel agent) under the Canadian resident promotion with a $300 discount on the cruise price. This special is not on their website. We booked a guarantee cabin and got upgraded 3 categories to an AX room 255. Windstar also offered a 20% discount on the price of internet, drink package and laundry if all taken together prior to cruise which we did not take as we did not care for the ship’s slow and expensive internet (we had access to a good roaming package which we used most of time as we were always close to islands).


We flew in same day with an early direct flight out of Montreal which arrived in SXM at 12h20 and we arrived quickly at the ship at 13h30 vs our 19h00 departure as we were, for the first time, travelling with only carry-on luggage which made for speedier exit of busy temporary SXM temporary airport terminal. Cabs were plentiful. Cab ride was $25 for the 2 of us and took 40 minutes (we stopped at Carrefour to pick up a couple bottles of wine which we took onboard). Check-in was swift at front desk given most of the initial rush had passed. Sail away was on schedule at 19h00. We were told our cruise was almost fully booked, so around 325 passengers on board. This was not an issue throughout the cruise as the Wind Surf remains very spacious with nooks and crannies for everyone.


We were in stateroom #255 (added to Wind Surf stateroom sticky forum). Staterooms are well designed with plenty of storage if required. The cabin was quiet and had no issues although we understand that at least on 2 occasions during the trip, staterooms located towards the back of the ship (not us) had vacuum issues with toilets not functional for several hours. Our room steward was attentive although we did not have any special requirements. Reusable water bottles we refilled every day with flat water and our ice bucket was kept full with ice every day.

Despite being much smaller than on the ones on motor yachts, the rooms are very well designed and we were really only in our room to sleep or change over for dinner. We did not use room service but did use laundry service with no issues. Bathroom is compact and well-designed but starting to show its age. No issues with hot water or water pressure throughout the trip. L’Occitane toiletries are provided in all rooms.

Bars and Entertainment:

Drinks were mostly taken outside at Compass Rose or Pool Bar. Did not have drinks in the Lounge as we like to be outside although it looked fairly busy in the evening. Bar service was always good. Duo at Compass Rose (D’Harmony) was OK and sometimes had guests dancing but generally it was pretty quiet compared to other Windstar cruises we have taken. We did not attend the crew show

Sail Aways were nice and the sails were up more often than in past cruises with our short hop from Anguilla to St Barth done on sail power only (3.5knots)

Dry Dock Improvements:

Although Wind Surf went into dry dock last November, changes to the ship remain minimal but include a totally renovated (incl. all furniture) and expanded Lounge (no more casino) which is much brighter than previously, the relocation of the Spa from deck 2 to deck 5 (in former Nautilus Room) and which is much larger and nicer than in the past when it was located at the back of deck 2, new chairs in Stella Bistro, a small waiting area near Amphora and new mattresses (firm) in all staterooms plus the addition of 16 new staterooms on deck 3 by reducing the number of suites. We heard onboard that the Wind Surf would get a total overhaul in 2023


Again food was a highlight. We ate at Amphora 4 times, one time each Candles and Stella Bistro and Deck BBQ on the late night in St-Barth. Dinner restaurant hours have been modified from 19h00-21h00 to 18h30-20h30. Given we are late eaters, it seemed we were always racing to meet this deadline. We preferred when restaurants closed at 21h00. Menu at Amphora changes daily and was varied with vegetarian and gluten free options available. Breakfast was good with buffet or a la carte items (waffles, eggs, pancakes, eggs benedict) available. Fresh squeezed OJ, lots of fruits, pastries, smoked salmon, cereal, oatmeal as well as several hot items (love their bacon) were available on the buffet.

We had good lunches at Veranda when we made it back in time from the island as the venue is only open from 12h00 to 14h00. Like breakfast, lunch consists of a buffet with hot/cold items, a carving station, pasta bar, burgers and other à la carte items that change every day. We were late a few times and had to “settle” for food at Yacht Club (very good sandwiches and energy bars). Lunch should be extended to 14h30 to accommodate those with dietary restrictions as the menu at the Yacht Club, while good, remains limited for them. Service in the dining rooms at dinner was fast and efficient with meals lasting 1.5 to 2 hours. We mostly had dinner around 8pm and never had to wait more than a few minutes for a table and by the time we were finished, most of the time we were the last table in dining room. Menus were varied with several fish, meat and vegetarian dishes and again were impressed by the quality and presentation of the food. Deck BBQ food was great although they ran out of lobster tails for those who came late which we thought was unacceptable. The Dining Under The Stars option which was offered twice on our Feb 2019 Wind Surf cruise not offered this time around. They had a burger bar lunch from 14h00-15h00 one afternoon but did not get to it as we were still on the island.

Beach BBQ was supposed to be held in Fischer’s Cove Virgin Gorda but was cancelled due to strong winds preventing the ship form having a sheltered anchorage so we spent the previous night and following day docked in Road Town for the day.

2 or 3 times during the week (maybe these were every night but I can’t confirm), we were treated to canapés at Compass Rose before dinner. Usually had 2 different types of canapés and staff did a few rounds so plenty to go around. We also saw these served in the Lounge.

Had dinner one night at Candles and everything was fine with tender filet mignon cooked to order. Don’t miss the prosciutto/parmesan potatoes. Note they no longer have Red Velvet cake on dessert menu. It had been a staple for several years.

We like the Stella Bistro and the French inspired food was excellent when we went

We are a bit picky about our coffee and the caffe lattes at Veranda in the morning were good (regular coffee not so much) but even better at Yacht Club (The barista on the Wind Surf however was not as good as Yogi on our November Star Legend cruise). We also did try a few of the sandwiches and sweets offered in the afternoon and all were excellent (try the Tuna and Greek sandwiches and the energy bars).

Also new was a tea station set up in Compass Rose in the afternoon which includes cucumber sandwiches and scones… and various teas. A good initiative that seemed to be popular with some guests

Although we do like our wine and drinks, for the second time in a row, we did not take any of the beverage packages available including a new one which allows you to purchases 5 bottles of wines in 2 price point categories at a 10-15% discount (several of the wines we liked were not on these lists). In the end it was cheaper, we drank better wines by the bottle and brought a couple of bottles we had bought on shore in St Barth (which they did not confiscate), to Candles and Deck BBQ and both times they did not charge the regular $17 corkage fee (they probably forgot, just too busy). Unfinished bottles were kept for next day and one time they could not find our bottle which had about a third left so they poured us 2 huge glasses of the same wine instead. Being a bit of wine buff, I find the wine list has a varied selection and decent prices. I posted wine and drink lists on Windstar forum last November and another cruiser recently posted them also.


We picked up our snorkel gear on Saturday night for our Sunday morning snorkel tour to the Indians although the tour provides its own gear if you forget. Due to the strong winds we did not see the marina open although a couple of times we saw them preparing it, just don’t know if they ever got to opening it formally as we were away on the islands and always came back too late


We visited the new spa but did not use it. Much better location and the spa itself looks very nice.


We did not use gym but it looked clean and well equipped and did not seem overcrowded.


Tender service was the only issue we had on this cruise. In St Barth, several people had to wait over an hour to 75 minutes for tenders going to and coming back from St Barth (was the case for the 2 couples we met on the ship). On our last day in Antigua, last tender was scheduled at 16h30. 12 of us were there at 16h15 when tender showed up but there were 12 other guests still on the island and instead of taking the 12 back to the ship as scheduled at 16h30 and come back for the remaining ones, we waited until 17h15 for all the late guests. They had plenty of time to have another tender run but for reasons unknown, the Bridge did not let the tender go. Guests were furious because we were kept in the dark and the Bridge’s decision did not seem to make sense from a customer service perspective. I have added more details on this on the Windstar Board under “Wind Surf Poor Tender Service”

Tenders were also used in Jost Van Dyke and Anguilla and we did not hear of any issues at those ports. The tenders themselves are also in need of a total overhaul. When compared to Seabourn, Club Med 2 and Star Clipper tenders, the Windstar tenders really look shabby. They will be changing the tenders on the Motor Yachts, they probably should do the same with the sailing ships.


We visited Bridge a few times and the on duty officer was nice and answered our questions.

Stops and excursions:

We generally are not the type to book ship excursions as we feel they are overpriced and like to do things on our own. I typically like to do my own research and do not like to plan too long ahead. On this trip, we had already been several times to all of the stops and were familiar with all of them so we knew exactly what we wanted to do.

Tortola (Road Town, docked):

Cloudy/rainy morning, overcast afternoon, light wind. Did ship sponsored snorkeling excursion to Norman Island. Good tour, not too expensive at $69. Snorkeling was ok at the Indians, better than the Norman Island Caves. Got back to shore around noon, had lunch onboard and went back to town and went shopping to Pussers. Town was quiet as it was Sunday and there was no other ship in town. Came back early and spent rest of afternoon on deck. This was our first time in Road Town and we liked it better when the Tortola stop was in Soper's Hole which I understand is being re-instated next year. Nice partial sunset cruise to Jost Van Dyke. They also ran tenders to JVD that evening until 12h30AM for guests that wanted to go to Foxy’s

Jost Van Dyke (Great Bay, tender)

Strong winds from the Northeast picked up during the night with heavy rains in the morning. Left ship around 10h30 under drizzle and headed to White Bay via taxi ($5/pers. each way 7 minute drive). Weather cleared up a bit by midday but was not great with some rain and some sun. Came back and had a few drinks at Foxy’s which has been rebuilt. Given the strong winds, Captain advised we would not be going to Virgin Gorda the following day (Beach BBQ cancelled) and instead would sail back to Road Town and dock for the night and next day.

Tortola Take 2 (Road Town, docked):

Finally a nice sunny day. We intended to go to Long Bay (West End) but were told by locals that the 20 ft seas offshore made for precarious swimming on all North Shore beaches so we opted to go Long Bay near Trellis Bay and airport which was sheltered. Taxi was $12/pers. each way (30 minute drive). Given there was also a Disney ship in town and that Long Bay seemed to be the only sheltered beach, it was a bit busy. It is a nice beach with chairs and all services. We went to quieter far end of beach and had lovely day. Came back to ship around 16h00. Overnight sail to Anguilla was very rocky with 12-15 ft waves. Several people including myself had a lousy night sleeping, the only one on this cruise.

Anguilla (Road Bay/Sandy Ground, tender):

Beautiful sunny day. We chose this cruise because it had this stop which Windstar only started doing this year and only appeared on 2 of the Yachtsman’s itineraries in 2019-2020 (normally replaced by a sea day). We have been to Anguilla several times and it remains one of the least developed islands in the Caribbean which is why we love it so much. It is renowned for its amazing soft white sand beaches which are considered by many (including myself) as some of the finest in the Caribbean if not the world. Given we had been to all of the most popular ones (Shoal Bay East, Rendez-Vous Bay, Meads Bay, Cove Bay or Crocus Bay), we decided to try lesser known Shoal Bay West (taxi $30 for the 2 of us each way 20 minute ride) which has nice beach restaurant called Trattoria Tramonto (free chairs if you have lunch). Very quiet (20 people max on a very nice and long sandy beach facing St. Martin). Came back to ship around 16h00 and had dinner at Candles that evening. Captain advised that because our sail from Anguilla to St Barth was so short (40nm) we would be under sail only most of the time with engines cut off.

St Barth (Gustavia, tender):

Beautiful sunny day spent at Pearl Beach Hotel on St Jean beach (Taxi 10 minutes, 20 Euros each way for 2). Rented chairs (30 Euros). Had lunch at small sandwich place later in St Jean Village (Kikiémoi). Did some shopping in St Jean. Took cab back to Gustavia where we did a bit of shopping (including wine at Cellier des Gouverneurs which we brought back on ship with no issues) and tender back to ship around 17h15. Our friends who took the tender a little later had to wait over an hour to get back and were late getting to deck BBQ which was held that night. Left St Barth at 22h00. Smooth sailing to Antigua that evening.

Antigua (Falmouth Harbour, tender)

Nice sunny day. Left ship around 9h30. 6 of us took a cab to Half Moon Bay, one of the nicest and least crowded (due to its remoteness) beaches in Antigua. Cab was $25 return/pers. 40 minute drive). A small restaurant/bar is now on the beach and they also rent chairs which is something new. Great sheltered beach (far end is nicer, less surf). On the way back, taxi took us up to Shirley Heights (part of Nelson Dockyards Park $5 entry fee) to take in the beautiful vista of Falmouth Harbour and English Harbour. Well worth the detour. Taxi dropped us off at the Dockyards where we spent an hour walking around and watching the racing sailboats coming in after their regatta. Got back to the ship only around 17h30 due to aforementioned tender issue.


Debarkation was trouble free. Had breakfast around 8am after picking up our passport and having face to face meeting with Immigration on board ship in the morning. Our flight was at 13h45 so we left ship around 9AM and went directly to airport (taxi was $10/pers. as there were 10 of us in the van. Despite all the complaints on the temporary terminal’s cramped spaces, we were through security and immigration in 40 minutes as we had no bags to check. Terminal was cramped but not as bad as last year. Flight back was uneventful and we made it back to Canada just as travelling restrictions were getting tighter due COVID 19. This concluded another wonderful Windstar cruise.

Misty Morning's Full Rating Summary
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Cabin Review

Deluxe Oceanview Stateroom

Staterooms are smaller than motor yachts but very functional. Being located on Deck 2 far away from tender exit at back of ship, this is a good location and no water sloshing on portholes like on Deck 1. No issues with the room. We were upgraded 3 categories from the Guaranteed room we had booked.

Port & Shore Excursion Reviews

Scuba Diving

Snorkel to the Caves at Norman Island (so so) and the Indians ( much better). We were approx 30 on the tour on a large power Cat. Plenty of room

View All 7 Scuba Diving Reviews

Great stop with great beaches and beach restaurants. A great island, like the Caribbean probably was 40 years ago


Half Moon Bay well worth the late no 40 minute drive.

Jost Van Dyke

A bit rainy but we managed a few hours at Hendo’s Retreat at White Bay

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