Windstar Wind Surf: Remote Caribbean Getaway

There has always been something so magical to me about a sailing cruise ship, which is why I was ecstatic to finally try Windstar Cruises' Wind Surf. This ship is one of two sailing ships the company operates and the largest ship currently in their fleet. On this sailing we would visit the islands of Antigua, Anguilla, Tortola, Jost Van-Dyke, Virgin Gorda and St. Barths. All this was round-trip out of Phillipsburg, Maarten. See my trip report on the JW St. Maarten to hear more about our pre-cruise stay.

Embarkation

This process was different from many of the other cruises I have sailed. Since it is such a small ship, only holding up to 342 guests, the check-in process was in a small building at the port of Phillipsburg. There was some initial confusion, which could be due to this being our first Windstar experience, as well as the fact that two other small cruise lines were using this same space for their check-in as well. But once we figured out where to get started, the rest flowed quickly. We arrived slightly before the 2 pm check-in time and were walking over to the ship about 15 minutes after we arrived. The walk to the ship from the check-in area was further than expected, so if you have mobility concerns, be sure to ask about assistance via the golf cart.

Once on the ship, we were greeted by a team of smiling crew members and personally escorted by one of them to our suite. It was great that we were able to get into the room right away to drop off our carry-on bags and to be guided by one of the crew members, which made it an easy and welcoming process. With our bags dropped, we made our way up a few flights of stairs to start exploring the ship. First stop: Stella Bistro to make our specialty dining reservations for the week.

Pro tip: All restaurants onboard are included in your fare, even the specialty restaurants. You will, however, want to make reservations for those once you are onboard as you are unable to do so prior to boarding. Wind Surf has two specialty dining options: Stella Bistro, the French-inspired restaurant, and Candles, a Windstar signature outdoor dining steakhouse. Each guest is asked to make only one reservation per restaurant on the first day so that all guests can reserve these experiences. However, they do welcome you to stop by during the cruise if you wish to dine in these venues again and they will accommodate you if they have the availability. No reservations are required for the main dining room, Amphora.

The ship

Porthole view

The ship itself is beautiful. They recently underwent a massive renovation of much of the public space, including the pool and Compass Rose bar, as well as an upgrade to the lounge with a floor-to-ceiling video screen. Some of the larger suites were also updated, however, the rest of the rooms will be competed in phase 2, sometime in 2026. The décor felt modern yet nautical to me. Lots of blues and natural woods, only enhanced by the number of windows looking out over the sea.

Pro tip: Be sure to connect to the Wi-Fi onboard, even if you have not purchased an internet package. Windstar offers a portal that can only be accessed while on the ship's internet and it is free of charge. The portal was extremely helpful in finding out what was going on around the ship each day as well as the dining/bar times. You could even pull up the dining menus for each restaurant.

Pool deck

Rooms

All rooms on the Wind Surf are considered suites. Something to note is that there are no balcony cabins on this ship. We were a little concerned with this originally, but once onboard, I barely gave it a second thought. Our cabin was on Deck 1 near the stairs and elevator, and we were never more than a few flights of stairs up to an outer deck. We truly didn’t miss the balcony in our room like we feared.

We booked the entry-level standard room with two portholes. The room felt spacious compared to the large ships we have been on. Plenty of storage with a plethora of drawers and closet space for us both to use during our seven-day sailing. The décor is a bit tired and dated, however the rooms are set for a refresh in 2026. If it is anything like they did with the public space, it will be a beautiful update. The bed was comfortable, however there was a lack of outlets overall in the room and none next to the bed.

Pro tip: Bring a power strip that can help you make the most of the two US plugs on the desk. If you have a European adapter, you can take advantage of the other outlet.

The bathroom was tight but manageable. Not a fan of the old-school shower curtains in the room, but nothing to fuss about. Lots of shelves and space for all our toiletries in the bathroom.

Bars

We never went thirsty during this trip. When we booked, we opted to purchase the all-inclusive package that would include all our drinks, Wi-Fi and gratuities. We felt it was worth it on this particular cruise as there were lots of beach days and fun in the sun.

Our favorite bar was the Compass Rose. This was a beautiful indoor/outdoor space on the back of the ship. You would walk up to the bar and order a drink and the staff would offer to bring it to wherever you were seated. Or, you could just have a seat and someone was never to far away to come offer their services. We also really enjoyed the bar snacks offered with each beverage. The staff was simply fabulous. This bar also offered entertainment in the evening with our favorite being the piano player. He had us laughing and singing along throughout the cruise.

Other options for a drink include the pool bar and a lounge mid-ship. The lounge was a great pre-dinner spot and made a fabulous martini. Here we also attended many of the port talks throughout the voyage and got some great tips on the best beaches and food and drink options for the next day. We made a point to check out that port talk each evening before dinner.

Restaurants

All your dining options are included on the Wind Surf. As I mentioned before, there are two that are considered “specialty restaurants” onboard, but they are included in your cruise fare. Most of our meals were in Amphora, the main dining room or up in the veranda.

The veranda is where we enjoyed all of our meals for breakfast and lunch. Here they do have a small rotating buffet that included made-to-order eggs in the morning and often a carving station at lunch. In addition to the buffet, there is a small menu of items you can order during breakfast or lunch. I would often order off this menu for breakfast and grab some fruit or a smoothie from the buffet while I waited. The food was always fresh and there always seemed to be a table free. We did not have to wait to be seated once throughout this trip which was a welcome surprise.

For dinner in Amphora, we were always able to get a table for two, which we prefer, and asked the maître d' each night. The menu was much more elevated from traditional cruise ship main dining rooms. We would often ask the servers for their recommendations and they never steered us wrong. The service was excellent in Amphora with everyone we interacted with being friendly and engaging. At one point when dessert was taking a little longer than expected, an assistant waiter came over to chat and presented to us a riddle. We could not figure it out for the life of us, but he made us laugh and barely notice the delay. Other than that evening, we felt the pace of the meal moved well and we had no complaints.

Stella Bistro is one of the specialty restaurants offering French cuisine. This restaurant was located on one of the upper decks near the front of the ship. The look is very different from the blues and dark woods in Amphora and hits you with some reds and off-white. A very different but welcome ambiance. The menu had many French classics to offer and I personally enjoyed the shrimp Thermidor and, of course, French onion soup. The menu does not change throughout the cruise in this venue as it does in Amphora.

Candles was the other specialty restaurant I was really looking forward to. The location is the same as the veranda, but at night this venue turns into the ship's steakhouse under the stars (or under the awning if you prefer). Think classic American steakhouse and it checks all the boxes. I had a wonderful salad, filet mignon and, of course, baked potato. We had a beautiful evening enjoying the Caribbean weather and delicious food.

Another great perk with Windstar is that room service is available 24 hours a day with options for breakfast, lunch, dinner or even just a snack. You could even order from the Amphora dining room menu during dinner hours if you wanted to eat in your room. We took advantage of the snack time offering a couple times throughout the cruise. My favorite was probably the popcorn for two, which we ordered one evening while watching a movie. It was a great touch.

Ports

Tortola

This cruise was port-intensive and a Caribbean beach lover's dream. Each day we visited someplace new — Antigua, Anguilla, Tortola, Jost Van Dyke, Prickly Pear and St. Baths. Each day, we took advantage of the beautiful weather and ventured out to try a new beach. Our favorite, and the one that was a big reason for choosing this cruise, was White Bay in Jost Van Dyke, where we visited the Soggy Dollar Bar. Kenny Chesney fans will get it, but truly this place was paradise for all who visited (which was a lot of people for such a small island).

Water Sports Marina

During some of the port days, the ship offered water sports from the marina off the back of the boat. This is something you would never find on the large mainline cruises and was a blast! Kayaks, SUPs, floating mats, a water trampoline and some regular ol' noodles to just float off the boat and enjoy the ocean. What a treat!

Debark

Farewell Party

Every cruiser's least favorite activity: debarkation. Thankfully, Windstar has it all figured out and this process was as quick and painless as it was to board. You are able to grab breakfast in the Verna restaurant prior to heading off the ship, which we did. Once off the ship, we walked back over to the port office to grab our bags, passports and exit through immigration. The whole process couldn’t have taken more than 20 minutes. Taxis were available as we walked out the door and our dream beach vacation came to a close.

Overall, this cruise ranks very high at the top of our long list of cruise vacations. I would love to help you plan your next journey onboard a Windstar ship!

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