In December, I had my first cruise with Windstar. Boarding the Star Legend in St. Maarten, my husband and I set sail on a romantic and adventurous itinerary with a cruise brand known for offering exceptional vacations and a reputation to back that claim. We had a week of sailing through the Caribbean, soaking up the sights in Antigua, the BVI, and St. Bart’s to create memories that will last for a lifetime and really get to know the Windstar brand. As an avid cruiser, this cruise’s price tag was a bit higher than my previous cruises. But, let me tell you how that extra bit more than makes up for it with these eight experiences that make a Windstar cruise worth the price tag.
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Windstar hosted me as a guest to familiarize myself with this brand. As always, opinions and reviews are 100 percent my own and unbiased.
1. Smaller Crowds
It might surprise you that the Windstar yachts only hold about 200–310 passengers. Not only is this a big difference in the mega cruise ships that often make you feel like a herd of cattle going through long buffet lines and waiting to disembark the ship at port, but it allows you to get to know the other cruisers. It also allows the crew to know you — your cruise preferences and your name. While I have met friendly cruise staff on each of the 50+ cruises I’ve taken, this was more like we were all just guests of Windstar, not crew and cruisers.
I especially think that, in the craziest of times we have faced since 2020, this is one of the most appealing cruise offerings possible. The Windstar team has assumed extra sanitation measures and are held to the highest standard of safety practices. This was apparent from the personalized service of staff members making up our buffet plates to the onboard doctor that was a seamless and pleasant transaction for the guests.
2. Windstar’s Stylish Yacht & Rooms
There are no cruise boats or ships with Windstar, only yachts and sailboats. I took the Star Legend, a small, incredibly picturesque yacht. The Legend was small enough to learn my way around in a short time, without wasting precious vacation time. Still, it was big enough to cuddle up for a warm-weather nap, read a good book, have an intimate conversation, or watch as we sailed through the mesmerizing blue waters.
Speaking only for the Star Legend, this yacht offers all-suite rooms. We even had a full-size closet, perfect for storing suitcases, hanging our clothes, and keeping our main room straight. Features in our stateroom that rated highest were L’Occitane en Provence toiletries, cozy robes, a comfortable couch, a heavenly bed, premium Egyptian cotton sheets, and a fully-stocked mini-fridge.
3. Lesser-Known Ports Of Call
I’ve studied cruise itineraries for over 20 years, and the ports of call for large cruise ships rarely change. I was shocked to see the remote destinations that Windstar Cruises travel to. My husband and I took the St. Maarten cruise that went to the British Virgin Islands, and though we had been to Virgin Gorda with others, Tortola and Jost Van Dyke were two places I’ve seldom seen on other itineraries. And we also had the chance to go to Gustavia (St. Bart’s), the island of all things luxury and exuberant.
If you are jonesing for a one-of-a-kind cruise, I’ll let you know that Windstar Cruises visits Tahiti, Kobe, Bordeaux, and Honfleur, not your typical cruise ports.
Pro Tip: Cruise lines can change the itinerary for the passenger’s safety and best experiences. This is common practice, so please roll with the punches should it happen. Often the passengers are unaware of the entire situation unfolding that causes these decisions.
4. Windstar’s Exceptional Food
When the general public talks about cruises, they tend to think of huge, overflowing buffets with mediocre food, but lots of it. And that makes many cruisers perfectly happy. I tend to lean toward quality over quantity, so the high-end food choices — many locally sourced — on Windstar Cruises made me a happy girl. Our meals were terrific!
Indulge in delightful breakfasts with an array of made-to-order eggs, fluffy pancakes, and decadent eggs Benedict. The buffet caters to all tastes, featuring a variety of Indian delights, smoked meats, comforting food favorites, soups, and sandwiches for lunch. With 24-hour room service, unlimited ice cream, and a charming coffee shop serving tempting mini-sandwiches and sweets, your culinary desires will be satisfied.
I was shocked (mic-drop here) that the main dining room — the basic one for those of you new to the cruise world — is the only cruise line at sea endorsed by and is the Official Cruise Line of the James Beard Foundation. Yes, you read that right. The foundation was created in part to recognize the efforts of those putting America’s culinary skills a cut above the rest, and that is apparent with the chef-inspired dishes on these ships. Windstar Cruises brings people to plates on the high seas that are “180 degrees from ordinary.”
5. Star Legend’s Specialty Restaurants
As if the food wasn’t remarkable enough, there are specialty restaurants on a Windstar cruise. The Star Legend had the lovely Spanish restaurant, Cuadro 44, and Candles, a classic steakhouse. Cuadro 44 offers coastal Spanish tapas, wines, and exotic seafood in a vibrant, energetic setting, while Candles is a more romantic restaurant with white table cloths, candlelight, and al fresco dining.
Now get this… they are included in your cruise fare. You pay no additional fees to dine in these restaurants that serve high-end items like Ibérico ham, lamb chops, Galician-style octopus, and jumbo prawns.
Fun Fact: Cuadro 44 only holds 38 passengers, so this small-scale dining experience is highly desirable.
6. Adventurous Cruise Excursions
I’ve been told that Windstar caters to a more active group of travelers. The website boasts 2,500 one-of-a-kind tours, and that is mind-boggling. I found many of the Windstar cruise excursions to be on the moderate to strenuous side of the scale, but there was still plenty for others to enjoy, too. From scuba diving to visiting private islands, there was a wide range of activities and experiences.
Windstar also offers many custom tours, including a carefully-curated excursion for your family and friends, or even a solo trip, to see the sights you wish to visit with an English-speaking guide in a private car or van. These guides are also fully bonded, insured, and licensed.
Check into the culinary shore excursions onboard Windstar Cruises, as well. These opportunities take cruise passengers to local wineries, breweries, and even hands-on cooking classes to learn from the locals and eat and drink with goods from the region you are visiting.
7. Ratio Of Cruise Staff To Cruise Guests
My cruise ship could potentially hold 312 passengers. On this particular sailing, there were only around 158 passengers, which meant running at half capacity for guests. This meant no lines, no packed swimming pools or hot tubs, and nearly 1.25 cruise staff per passenger.
I swear, I don’t know how the Windstar staff does it, but they would remember every name, drink (alcoholic and non-alcoholic) choice, favorite things, and where we were from. Often, we didn’t have time to think we needed something before a smiling face showed up with said item in hand. I kept thinking of the Ritz Carlton tagline, “My pleasure Mrs. Pittman.”
Fun Fact: For even more excellent cruise concierge service, allow Windstar to help you book your air travel, pre and post hotel and tour reservations, and even your itinerary for a fantastic vacation.
8. A Unique Beach Barbecue Dining Experience
Something new to my cruising experiences happened on the Windstar Star Legend. It was supposed to be two things, but one got postponed and then canceled due to inclement weather. But, the one that did take place was incredible, and I think you will agree.
In a port where we had to tender (take small boats) to the shore, Windstar set up a beach barbecue for all of its guests to enjoy for lunch. Virgin Gorda was the perfect setting for the festive tables, steel-drum musicians, paella and bbq meats buffet, and tropical backdrop. The amount of effort that went into shuttling all things necessary (plates, glassware, utensils, food, beverages, linens, etc.) to the shore for us to have a memorable lunch honestly brings tears to my eyes. What a fantastic brand and staff that braves, in our case, extreme waves and weather conditions for a quick dining experience that creates such a heartwarming memory. It was well-appreciated.
Windstar, if you made that macaroni and cheese because I mentioned it, thank you. They canceled the deck barbecue mentioned above due to the weather, but I heard from repeat passengers that this is one of their favorite Windstar offerings.
Pro Tip: I like to bring a few cards from home and leave a tip for my favorite cruise staff, along with a personalized message to thank them for enriching my vacation.
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