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My Amazing First Sailing With Windstar

My Amazing First Sailing With Windstar

My husband (Eddie) and I boarded the Windstar Legend in December 2021, shortly after cruise travel reopened from the pandemic. Here is what to expect on your first sailing with Windstar Cruises.


Knowing what to expect from a cruise is half the battle in planning a successful vacation. My family and I love cruising, so that narrows my choices to ocean or river, but there are many cruise lines to choose from. We have sailed with eight of them, so it was a real thrill adding cruise line number nine to our travels with a Caribbean cruise from St. Maarten.

The Windstar Sailing Vessels

You will either be cruising on an award-winning sailboat or all-suite yachts when you book with Windstar. Our cruise was aboard a yacht, the Windstar Legend, but we were side by side with the Wind Surf for embarkation and at one of the cruise ports.

The Star Legend holds slightly more than 300 guests. Our sailing was at 157 capacity, which meant we had the floating hotel basically all to ourselves. It was intimate enough to make some really great friends, but there were still people at disembarkation we had never seen.


Pre-Travel Overnight(s)

Since we were flying from Texas with a connection into St. Maarten, we came two days early. Or at least tried to. You can either make your own hotel arrangements or allow Windstar to book for you; we chose the latter.

Eddie and I touched down in St. Maarten around 3:30 PM, later then we anticipated. We had purchased transfers with the cruise line, which were null and void since our flight had to be changed, so we grabbed a cab to the hotel. Our lodging was at the Hommage Hotel & Residences in Marigot on the St. Martin French side of the island; the ride was 35 minutes with traffic. 


The Hommage Hotel was heavily decorated with art installments, sculptures, murals, and stylish spaces, with an onsite restaurant that included a complimentary buffet-style breakfast. Our room was huge, with comfortable furnishings, nice linens, a wonderful bathroom, and was steps from the beach.

The cocktail bar and swimming pool were busy with guests during our stay. You could spend hours roaming the grounds and enjoying everything to look at.

For dinner, we took a taxi to Be Cool, a restaurant recommended by a friend. Prepare to spend two to three hours for dinner, as the service is European style, and they are incredibly short-staffed. It was delicious and not a bit overpriced.

The restaurant called us a taxi to get back to the hotel (5 USD per person) and ensured that the taxi driver came to the restaurant and physically escorted us to the cab.


The Windstar Cruises Arrival and Boarding Process

The following day, our shuttle was there to take us, plus a few other guests, to the ship. St. Maarten’s traffic was really hectic, being the holiday season, so the ride took 50 minutes. Our bus was very comfortable and air-conditioned, and the staff was helpful.

I failed to mention that the Windstar staff was set up in the hotel lobby and available to answer questions and make suggestions all evening and the morning of embarkation.

At the cruise terminal, we handed off our suitcases to be transferred to our stateroom, went through a scanning device, and showed appropriate ID and forms. We were steered into an area for the final boarding process, added a credit card to our account, and picked up stateroom cards.

Throughout the process, we were photographed and then taken in groups to the ship’s doctor, who conducted a free COVID nasal swab (December 2021, when it was still necessary).

windstar alcoholic-beverage-package

Next, we learned about the alternative dining rooms on Windstar Legend and booked a meal time to dine at Cuatro 44 and Candles. The Windstar beverage program was explained to us, and interested guests signed up at that time.

The alcoholic beverage package has two levels, priced per day, per person, for the length of the cruise. I would recommend one of these packages for your first time sailing with Windstar, to enjoy your vacation to its fullest.


Unlike a few other cruise lines, guests in the same cabin do not have to package the same drink package. It is worth noting that coffee, tea, soda, and bottled water are complimentary on Windstar Cruises, and you do not need the drink package to enjoy them.

From start to finish, the check-in process took about 30 minutes.


Windstar Staterooms

Eddie and I stayed on deck six of the Windstar Legend. Our room was so spacious that I nearly did a double take. I’ve sailed more than 50 times and not once had a stateroom that could compare to this one. It was stylish and comfortable, and the design made great use of the space.

We had an incredibly comfortable king-sized bed, a flat-screen TV, a desk and dressing table area, and a couch with two chairs.


Eddie’s favorite part of the room was the Juliette-style balcony that allowed us to see outside, get fresh air, and get some great photos. Mine was the spacious bathroom with a double sink. The shower was fabulous, with rounded doors on a track and a high enough enclosure that the water did not slosh out.

Windstar uses L’Occitane toiletries, which gets a big thumbs up. There were also small shelves on the side and a cabinet that ran the length of the sinks for holding cosmetics, hair devices, sunscreen, and other necessities.


Our room also had a large walk-in closet, something I’d never had on a cruise ship. It was lighted, with shelving, hangers, robes, and an in-room safe. We had plenty of space to store our suitcases once we unpacked them.

And between the closet space, the shelves, and the three big drawers in the bedroom area, we were set.

Windstar’s Food

There is a reason cruise ships do not have scales in the bathroom. The food onboard was exceptional, and Windstar is the only cruise line endorsed by the James Beard Foundation. For breakfast, there are three choices to eat: room service, Veranda, and the Yacht Club, basically the coffee shop with limited food choices.


The Veranda (which transforms into Candles for dinner) is where you’ll find the buffet-style breakfast. It has a nice selection, a bit of everything, including five to six made-to-order dishes (pancakes, waffles, etc.), and a custom egg station. Veranda has indoor and outdoor seating. I loved the Eggs Benedict, cooked to perfection each time.

If you’d rather enjoy breakfast in the comfort of your room, call room service for a continental breakfast or bacon and eggs to be delivered at whatever time you choose. This is helpful on port days.


For a quick breakfast or lighter options (smoothies, yogurt, or fruit cups), The Yacht Club at the back of deck eight is where you’ll want to go. I highly encourage you to try all three at some point.

For lunch, you have the same choices only with the addition of the poolside bar, which is out by the deck 7 bar area. This is an order-from-a-menu option with quiche, burgers, and salads. You may want to treat yourself with a cone of ice cream afterward, beside the food bar.


Windstar Dinners

For dinner, all guests get a seating at Cuatro 44 (Spanish tapas), and Candles (the classic steakhouse), while the rest of your meals are in the main dining room. The food was great everywhere, but the main dining room was my favorite.

Expect dinner entrees like Grilled Bronzino, Moroccan Glazed Shrimp, Broiled Corn-Fed Veal Chop, and Roasted Lamb Rack. Side items included sautéed asparagus, Panko-coated onion rings, broccolini, and creamed spinach. For those with a hearty appetite, you may consider the 40 oz. Beef Bone-In Ribeye Tomahawk Steak.


As always, room service is always an option. We ordered room service once, chicken quesadillas for lunch, and they were great. The delivery was prompt, and it was an easy process to order.

To learn more about the amazing food on Windstar Cruises, you will find this post helpful.

Onboard Activities on My First Sailing with Windstar

Windstar delivers a daily newsletter to your stateroom to keep you abreast of the ship’s happenings. It includes the ports of call, a brief overview of the area, where the other Windstar yachts are on the same day, temperatures, sunset time, and what you can do around the ship throughout the day. Those activities might range from scavenger hunts and trivia to a daily lecture series which I especially liked.

One day we discussed travel, while another day, it was wildlife.


I spent a lot of my time at the pool and hanging out in the hot tub talking to other passengers. The spacious deck was nice for walking and napping. We loved the round lounge beds that allowed for a bit of privacy and protection from the sun.


Windstar’s Staff

If Windstar were a casino game, their friendly, energetic, and professional staff would be the grand prize. Windstar’s team sets them apart from the competition in ways I never knew existed. The yacht was beautiful, the food magnificent, and the ports of call exceptional, but I’m typically pleased with those things on every cruise.

The staff appears to be the reason that out of 157 cruisers; one couple had sailed with Windstar over 100 times, 4 (that I met) over 50 times, and several multiple times. Eddie and I were only two of the eight newbies aboard.


By day two, nearly every crew staff member we came in contact with knew our names. They always took time to speak or strike up a conversation and were at our beck and call within seconds. By day three, I think they learned everyone’s beverage preferences and worked tirelessly to keep things tidy and make us feel special.


Windstar’s crew has exemplified leaders of the hospitality industry, from the spa technicians to our waitstaff, room stewards to the Captain and officers.


One night towards the end of the cruise, the Windstar staff is responsible for the evening’s entertainment. Crew members sign up to dance, sing, showcase their talents, and make us laugh…and cry. This was a first for me and my favorite night of the cruise. I think everyone else agreed.

From Anda, our favorite servers, singing to a group of bartenders doing a synchronized swimming comic skit, I laughed until I cried. It was sensational, not to mention creating an even deeper bond between Windstar staff and guests.

If you’ve sailed with Windstar, you know the feeling that truly cannot be described but is welcomed with all sorts of feels.


Ports of Call

Our St. Maarten cruise itinerary had changed twice before boarding the ship. During a time with uncertain COVID numbers and different rules for each country, Windstar worked hard to ensure that the passengers were safe and had a great vacation but were not over-tested and made to incur additional expenses. I appreciated this greatly.

Even so, with the omission of Montserrat and St. Lucia cruise ports, we were COVID tested three times; to board, to fly home, and once because it was a BVI requirement.


Our cruise ended up sailing to St. Barthélemy (St. Bart’s), Antigua, and had three stops in the BVI: Tortola, Jost Van Dyke, and Virgin Gorda.

I highly recommend taking excursions with the cruise line, as they have provided the best of the best to lead your tour. But, if you’ve already been to the cruise ports, you may want to explore on your own, which we often do. Sometimes it is fun to just see what you can find with no agenda.

star -egend

Our Port Excursions

We did an hour-long island tour In Gustavia, St. Bart’s (St. Barthélemy), then walked around the downtown area to see the mega-yachts. We did some shopping and saw where the rich and famous come to play and be seen. There are great photo ops along the harbor.


In Antigua, we strolled around, visited the historic St. John’s Cathedral, and had drinks at Hemingways Caribbean Cafe, something we always do there. The tropical fruit flan is pretty darned tasty, but this time I tried a perfect affogato.


Antigua’s beautiful church has seen much progress in its repairs and restoration since our last visit. The stained glass windows are stunning. If you are soda fountain drinkers like we are, here’s your chance—there’s a local McDonald’s nearby.


British Virgin Islands

In Soper’s Hole, Tortola, we took a five-hour island tour, which allowed us some time on our own. We shared a tasty chicken roti at a beach restaurant (Paradise Club Lounge, Bar, & Restaurant) while soaking up the incredible views.


In Jost Van Dyke, an area in the BVI we were unfamiliar with, there were only scuba diving excursions offered, which we did not want to do.


Instead, we paid $5 each to take an open-air vehicle to the back of the island for the best day ever. Soggy Dollar is a World-Famous Beach Bar with a riveting DJ and music scene, great drinks (hello, Bushwhacker), food, and all the beach offerings you could ever want. The row of lounge chairs lining White Bay’s stunning beaches in each direction was the perfect place to hang out for the day.

Pro Tip: The Pain Killer drinks are all the rage. Pair it with the yummy Chicken Roti.


At Virgin Gorda, I couldn’t wait to take my husband to The Baths, something I’d done with my daughters years ago. We took an hour-long island tour and then had time to hike down to the beach at The Baths, soak up some sun, and then head back to the cruise pier.

Fun Fact: The Baths of Virgin Gorda is a National Park.


The landscape is fantastic at The Baths, and if you aren’t in excellent shape, there is a shortcut path to get you to the water’s edge quicker and easier. Don’t be afraid to take that route instead of the one with ladders, ropes, caves, and a very physically challenging landscape.

Grab a bite in the cafe at the top of the hill. They make excellent conch fritters and have a swimming pool and great picturesque views of the gorgeous island.


Windstar Cruise’s Special Amenities

Windstar has many exceptional amenities, but two were highly noteworthy. First is the water sports platform. I had no idea about this until I saw it on my stateroom TV video. Then, many guests who had done it on previous cruises were talking about it.

Windstar has water trampolines, inflatables, kayaks, paddle boards, windsurfers, snorkeling gear, and water skiing that they sometimes roll out of the ship aft for the guests to use at no additional charge. I saw the area where it was all housed, and while it sounded entertaining, the weather did not cooperate for us to use it.


The second is a luncheon beach barbecue. Keep in mind that we tendered to shore at four of the five ports of call (Antigua has a pier), meaning that smaller boats took us from the ship anchored in the ocean to the beach pier.

The tenders can hold 80 passengers comfortably, but due to only having 157 guests and many not getting off the boat at the earliest time, we could all fit in two quite easily.

On our day at Virgin Gorda, the Windstar crew and staff hauled our food, linens, plates, silverware, etc., to a beach where they set up a fantastic beach picnic. Even after the waves were too high for our usual docking area, Windstar persevered to ensure that the guests were treated to this unique offering.


A Feast Fit For A King

We enjoyed steel drum music as we dined seaside on a feast of ribs, sausages, jerk chicken, beef, plus sides of macaroni & cheese, corn on the cob, and baked beans, to name a few. There was fresh fruit, cake, and cookies for dessert.

Before all the guests were through the line, the rain rolled in and nearly crashed our party. Luckily, we were at a restaurant’s beach, so many of us took over the tables on the deck and inside the restaurant. The staff never faltered; they kept clearing dishes (real ones, not disposable), refilling drinks, and mopping up water just as quickly as it landed. I was in awe.


There is also, typically, a Windstar barbecue dinner, but ours was postponed due to high winds and then canceled the next day due to exuberant winds. December in the Caribbean was pretty brutal with the squalls and moody weather.


My Review

I think it is apparent that I loved my first sailing with Windstar Cruises. The attention to detail and high customer satisfaction are easily conveyed in everything they do. The size of the cruise is a tremendous asset, and the service level is another. The ship is attractive without being fussy, organized, well maintained, and aesthetically pleasing.

I cannot wait to see where else I will visit with Windstar Cruises.


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