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Wind Surf Review

4.0 / 5.0
256 reviews

Great Yachtsman’s Caribbean Cruise

Review for the Caribbean Cruise on Wind Surf
Misty Morning
10+ Cruises • Age 60s

Rating by category

Value for Money
Public Rooms
Fitness & Recreation

Additional details

Sail Date: Mar 2020
Cabin: 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).

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 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

43 Helpful Votes
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