What’s it like to sail on a cruise ship that actually sails too? Come along as we find out cruising the Caribbean on Windstar Cruises’ flagship Wind Surf!
Windstar Cruises is known for imaginative itineraries and last year’s Hurricane Irma inspired them to get even more creative. As someone who enjoys traveling off the beaten track, I was thrilled to experience cruising Windstar’s Jewels of the Windward Islands.
Cruising on the Wind Surf is a little like chartering a yacht with a lot of new friends. At 617 feet long with five masts, seven sails, and just 310 passengers to the sailing ship’s 200 crew, you could almost call it a private yacht on steroids.
Their tagline is “180° from Ordinary,” and it is apt—banish all thoughts of small cities afloat, long lines, theme nights, or stuffy, formal evenings. Cruising on these small ships is a casually elegant affair.
It attracts a well-traveled clientele who appreciate a distinctly small ship experience. The feeling is boutique, visiting small ports that those big cruise ships can’t. The common areas never feel crowded, and the imaginative shore excursions are a nice size.
The staterooms have a mini-superyacht feel with storage in an elegantly rounded design and a lux decor in general. I appreciate their choice of L’Occitane care products—there was no need to bring my own. The first night as I open the L’Occitane Extra-Gentle Verbena Soap, the delightful fragrance wafted through the cabin as the waves gently rocked me to sleep.
The Wind Surf crew is made up of 27 different nationalities, mostly from Indonesia and the Philippines. Captain Pedro Pinto hails from Lisbon and destination manager James Anderson Smith is from England and it’s fun to hear the different accents. The staff gets to know you throughout the week, and some call you by name. “Hello Miss Kara,” became a familiar refrain.
The officers were particularly memorable; Windstar has created a perfect cast on the Wind Surf. From the always charming Captain Pedro Montes Pinto to Vitor Duarte, one of the most entertaining sommeliers ever (wait until you see him dance), to the maître d’hôtel Merrick Saldanha who, when sensing a dish wasn’t my favorite, brought a wonderful seared tuna, my favorite of the cruise. James imparted his delightful brand of wit and wisdom while sharing his knowledge of each port and inspired us to explore all that Windstar offers both on and off the water. Aimee at the front desk was also a godsend, so knowledgeable and helpful, even popping down to my stateroom to help me with a zipper on a strapless sundress.
Windstar’s ships are renown for being able to enter the small ports those monster cruise ships can’t, and the Jewels of the Windward Islands is a perfect example. We visited the stunning and unspoiled St. Vincent and the Grenadines and beautiful Mayreau. Having our own private party there makes it all the more special. Bequia, the second largest island in the Grenadines, is a charming little village, and just strolling the picturesque little island is an experience not to be missed.
Destination manager James Smith has curated a delightful selection of experiences for passengers to experience off ship, everything from a Martinique snorkeling trip to the Anse Dufour reef and bat cave (yes, bat cave—how often do you see beautiful fish and bats in one tour?) finishing with a yummy rum punch, to a hands-on learn-to-sail program in St. Lucia aboard First 4 Sail, a retired race boat (super inspiring to see these brand new sailors take flight), and an aerial tour of St. Lucia’s rainforest.
It was a beautiful day of sailing aboard First 4 Sail, and I’ll always remember first-time sailor Jane Welch from Canada completely rocking the helm and how new sailors Anika and Renee Hochauf from Germany embraced the sport. Veteran sailor Pete Kuhn had high praise for the experience: “It was terrific. [instructor Ben Thompson] explained sailing in a direct and understandable way. And it was fun to sail, as a retired performance boat, it wanted to perform—it moved!”
Traveling alone this time, I elected to take more shore excursions than I might normally. I can proudly say that I’ve snorkeled and communed with bats (albeit rather briefly thankfully), enjoyed sailing St. Lucia, and getting a bird’s eye view of the island’s lush rainforest (seeing the diversity of the island was one of my favorite experiences during the cruise). I enjoyed the picturesque port of Grenada and a delightful Snorkeling Champagne and Lobster Cruise (Note: They currently serve Cook’s, so oenophiles should opt for the rum punch unless you’ve got a hankering to revisit your college years). The beach days at Mayreau and Bequia were a relaxing, beautiful, and pleasant respite from the ordinary.
Where to dine
Amphora is the primary restaurant aboard Wind Surf, and there is also Stella Bistro, contemporary dining with a French accent, and Candles for steakhouse-inspired al fresco dining. Spoiler alert: Executive chef Stephan Vasilev is based in Amphora, so it shouldn’t be too surprising that several guests said that’s where they had their best meals. And the bonus—reservations are not required for Amphora. Reservations for Stella Bistro and Candles are competitive, so schedule early.
I had delicious meals at all three restaurants. I enjoyed the diverse variety of entrees at Amphora, where one evening you might see a French favorite alongside a creative Indian dish. Many memorable dishes come from Windstar’s partnership with James Beard Foundation chefs, which are highlighted on the menu.
The Francophile in me still dreams about the delicious onion tart at Stella, and the steak at Candles was quite delicious. Breakfast at the Veranda was so yummy it inspired me to rise a little earlier so I’d have plenty of time to savor every bite. You can order off the menu or enjoy the fresh buffet featuring an omelet station.
The Yacht Club, a little cafe, is an excellent choice for a quick meal or grabbing something in-between dining hours. I particularly liked their mini gourmet sandwiches.
Wherever you dine, there is no need to worry about choosing the wrong dish. If it’s not a match for your palette, simply ask for another. Can’t decide? Order both. One night the filet and seafood dishes looked equally appealing, so they created a surf and turf entrée just for me.
Who you’ll meet
During the first part of the cruise, I asked to join others for dinner and met some interesting people, like the stylish Julia and John from Oklahoma. I admired Julia’s fashion sense and her ever-changing David Yurman bracelet collection. It was so fun to chat; her husband sounded just like Matthew McConaughey!
Shore excursions were another great opportunity to meet people. I met fellow solo traveler Diane Tsonos on the Anes Martin snorkel trip. Daine, a Montreal tax attorney, has previously chartered 40 to 50-foot sailboats in the Bahamas and BVI with friends and family but decided to leave the sailing to someone else this time.
Newly single she said, “I’m always the organizer whenever traveling, and thought I might as well organize one for myself.” The trip was a spontaneous decision; she booked just two weeks prior. “It’s delivered greatly,” she said smiling.
Later that evening, I met more sailors, and members of the Cleveland Yacht Club enjoying the Commodore’s Cruise. I learned that the CYC has the distinction of having no less than six beautiful classic R boats.
Commodore Larry Greathouse had high praise for the cruise. “For the yearly Commodore Cruise, I was inspired to select a small boat/small island getaway that appealed to both sailors and power boaters at the CYC. The Windward Islands and the Wind Surf more than met our expectations and our members all had a memorable and fantastic experience.”
Also impressed with the cruise were third-time guests Rob and Patti Gaulin of Greenwich, CT. “I love the Windstar attitude, the privacy, and tranquility. It’s so uncrowded,” said Patti.
“The big ships are shows. This is more relaxed,” chimed in Rob as he savored his cigar in the Cigar Bar.
“You meet the most interesting people on a Windstar Cruise, and it’s really laid back. When you have a big job, you don’t need the excitement,” reflected Rita Startup, assistant dean of development at NYU. I agree with Rita. Vacation for me means a time to relax. I didn’t miss the shows and high-profile entertainment of other cruise lines in the least.
What to wear
Dressing for dinner is as easy as throwing a tunic over some capri pants or slipping into a simple sheath. If you’re feeling especially festive, wear a beautiful sundress like Ralph Lauren’s Jardon Floral Silk Halter Dress, a stunner from the recent show – really anything from Ralph Lauren’s dress and jumpsuit section will do. Or, you can pack light and have your stylish coverup do double duty over capris. Tory Burch’s Kaleidoscope Beach Kaftan would look great over white.
If you travel light or just hate ironing like me, Windstar’s unlimited laundry package offered on the first night is a godsend. Rather than spending my first evening ironing, I was making new friends over drinks and enjoying the stunning sunset.
The days are warm in the Caribbean so shorts are the order of the day. My favorites for this trip were my J. Crew Scalloped Shorts in a nice linen/cotton blend. I love how the hem mimics waves—perfect for a cruise! I paired them with some simple but elegant linen and silk tops from Ines de la Fressange Paris (a fav style icon and fashion brand) and Jack Rogers cork Napa Valley Sandals are a wonderful neutral color that goes with anything.
I received the most compliments by far for my Soeur du Maroc Marrakech Medium Straw Tote with fun pom poms. If I’d had extras along, I could have sold them on the spot!
Where to shop
Shopping wasn’t a focus of this trip, although the Ship’s Store offered some great finds. A few that came home with me were a silk Gretchen Scott tunic, a nice addition to my collection, a pretty semi-precious stone, and shell necklace, and a Sea Bags Envelope Clutch in black Dacron, a new favorite item. I’ve carried it several times, during the cruise and since being back.
Manager Clara Rances said the most popular items on this cruise, and most, in general, were the 180° from Ordinary t-shirts. Windstar boasts a truly impassioned client base. It was unusual to meet someone who hadn’t cruised multiple times with the line—three, six, 10, 15, or even more.
Wind Surf’s signature Sail Away: It’s a magical feeling listening to 1492, the Conquest of Paradise Theme, while those majestic sails unfold (all 21,570 square feet of cloth!) as you leave port.
Make time for the Marina: This is your own superyacht experience. The back of the ship opens to create a swimming platform offering all kinds of watersport-related fun—a trampoline, paddleboarding, kayaking, sailing, and more.
A visit to the bridge: Very few cruise lines have an open bridge policy. Don’t miss this opportunity to see the nerve center in action and learn exactly how these professionals get us to these wonderful exotic destinations.
The executive chef’s cooking demo: Chef Stefan demonstrated how easy it is to make a delicious shrimp and scallop risotto. You won’t want to miss this bit of alchemy.
A day before and a day after Cruisers know to arrive a day early, known as a “just in case” travel day, but I recommend staying a day after as well. Don’t go for the early flight; rise leisurely and enjoy more of beautiful Barbados, which has so much to offer, particularly for sailors. It’s the birthplace of Mount Gay Rum (the visitor center tour is a must) and of course, the lovely Barbados Yacht Club!