Cruising the Caribbean on Windstar’s Splendid Sailing Ship

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.

The yacht

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.

One of the best things about cruising on the Wind Surf is the specialness of the ports visited. She can visit ports the big cruises can’t. Here we are moored in the Grenadines.

A magical Mayreau sunset, one of the hauntingly beautiful places we visited.

A cocktail named Smooth Sailing? Yes, please!

There is a certain romance about Windstar’s Wind Surf. Sunset is my favorite time, few things compare to enjoying a cool drink in the warm air while watching the sunset.

Sunset is a magical time on the Wind Surf.

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.

Wind Surf staterooms have a mini-superyacht feel. The fresh tropical flowers and L’Occitane products are a nice touch. I loved the welcome Veuve Clicquot and strawberries, thank you Windstar! Photos: top Windstar, bottom row Sail Couture.

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 crew

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.

Clockwise from the top: Destination Manager James makes you want to sign up for everything!, so many nice staff, here a proud pastry chef showing off his surfboard cookies at the start of our private party on Mayreau, maître d’hôtel Merrick sans his crisp white uniform for the party off-ship. Vitor—a sommelier with a personality and then some, and adorable Aimee at the front desk, ready with a quick answer to anything. Photos: Sail Couture.

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.

The itinerary

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.

St. Lucia is so much more than beautiful beaches: Scenes from the Rainforest Aerial Tram Tour where open-air gondolas give you a bird’s-eye view of rainforest flora and fauna. Our nature interpreter Donnisha points out interesting trees, plants, and birds. I’m especially taken by the panoramic view at the top of the line of the enormous giant tree ferns. The foodie in me is interested to learn fiddlehead ferns are there, too. And fun fact—possum is a delicacy in St. Lucia! Photos: Sail Couture.

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.

Fun on the learn to sail excursion in St. Lucia, clockwise from top left: a view of our home for a week the beautiful Wind Surf, Renee Hochauf learning to hoist, Pete Kuhn, who sails a J/33 back home all smiles, new sailor Jane Welsh totally rocking the helm, Anika’s a natural there too a says she’ll definitely go sailing again, heading toward the Pitons and our trusty steed for the day, First 4 Sail.

Snorkeling Martinique style! Clockwise from the top: Benoît calls us back from snorkeling by conch shell, “There are bats in that cave!”, returning to Anse Mitan, and a baby sea urchin. No great snorkeling photos as my underwater camera didn’t survive the flight alas. Photo: Sail Couture.

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!”

Snorkeling champagne and lobster cruise aboard the Shadowfax catamaran in Grenada. Top row: They are as yummy as they look! Second row, left to right: lunch is served, fish soup to start, chef at work. Third row: under sail, rum punch, topped with Grenada’s signature spice nutmeg, and a view of picturesque Grenada from Shadowfax.

Beach time…enjoying a little R&R in St. Lucia.

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.

Who says you need to gain weight on a cruise? Windstar has wonderful healthy options like this seared trout over greek salad.

Enjoying lobster and suckling pig while dining under the stars.

Seriously yummy. The James Beard Foundation’s Grilled Guajillo Glazed Prawns with charred corn relish and creamy polenta by Annie Pettry of Decca in Louisville, KY. Fans of Top Chef will recognize Pettry from season 14! Photo: Sail Couture.

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.

Amphora’s delicious seared tuna. Yes, I did enjoy the steak on the cruise, it just wasn’t quite as photogenic as the seafood!

Olé! Spanish eggs at Veranda.

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.

The Cleveland Yacht Club is contingent on their annual Commodore’s Cruise. Photo: Windstar courtesy of Larry Greathouse.

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.”

New Sail Couture gals from the cruise, clockwise from top left: first-time cruiser Kristine Price from Loudon County, VA, studying the fish guide on the Bequia Snorkel trip, the ever-stylish Yvonne Collvon leaving the ship, Julia from Oaklahoma enjoying some pool time, Julianna Caplan and Heidi Mitchell (Heidi was on assignment for Travel & Leisure), fellow Californian Cara Ferrara enjoying the gourmet catamaran cruise, Viktoriya Romashko from Ukraine with Assistant Destination Manager Jona Pakingan from the Philipines, and Peggy Murphy of London and Alicante.

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.

It’s casually elegant on a Windstar Caribbean Cruise: a Tory Burch Kaleidoscope Caftan can do double duty at the beach or over capris at dinner, a Ralph Lauren Jardan Floral Silk dress when you want to feel especially elegant, J. Crew Scalloped Shorts for the day, Jack Rogers Napa Valley Cork sandals with anything anywhere, and my fun Soeur du Maroc Marrakech Straw tote from Bloomingdale’s – the hit of the cruise! Photos: Ralph Lauren, Tory Burch, J. Crew, Sail Couture.

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.

Ships Store Manager Clara Rances models the most popular purchase on the Wind Surf—the 180° t-shirt, my favorite two new acquisitions: a Sail Bags sailcloth clutch and Gretchen Scott silk tunic, Bequia female entrepreneur Molissa Samuel wearing her signature Mermaid Necklace, necklaces on display at her stand and uber-chic Lisa Lavelle wearing her mermaid necklace. After I complimented her on hers, she told me about Melissa, who is easy to find, right by the big Bequia Youth Sailing sign. Photo: Sail Couture.

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.

Can’t-miss moments

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.

The Wind Surf sports brand new sails by Incidence Sails of France. It’s very cool to watch those enormous sails unfold one by one!


The Wind Surf’s aft door opens to create the marina featuring all sorts of watersport fun.

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.

Captain Pinto at the helm. He told me that on two nights during the cruise, we used sail power alone for six hours straight. Windstar has an open bridge policy, make sure to visit! Photo: Sail Couture.

Executive Chef Stefan Vasilev demonstrates how to make a simple, yet delicious, seafood risotto in the cooking demo, and later prepared for the evening meal during the kitchen tour. Photo: Sail Couture.

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.

Scenes from the lovely Barbados Yacht Club: Melissa Boland sailing her Laser Radial, the beckoning white sand beach, the YC’s famous flying fish sandwich. Photo: Sail Couture.

The Mount Gay Rum tour is a must for rum-lovers, clockwise from the top: welcome cocktail, signature rum tasting, bartender Ryan mixing a craft cocktail, detail of that delicious cocktail, a tour par excellence by brand host Romal. Photo: Sail Couture.

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!

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