Escape to the Caribbean: Sailing the Windward Islands by Private Charter

WARNING: FOMO ALERT!  This month’s dispatch from our favorite luxury traveler, Jamie Edwards of I am Lost and Found, is sure to be FOMO-inducing.  Consider yourself warned!  Jamie rarely takes the same trip twice, but she’s chartered a private yacht in the Caribbean multiple times in the last decade and you’re about to find out why.  Come sail away with us to the easy, breezy Windward Islands.


“Twenty years from now, you will be more disappointed by the things you didn’t do than those you did. So throw off the bowlines. Sail away from safe harbor. Catch the wind in your sails. Explore. Dream. Discover.”

With the phrase ‘social distancing’ firmly in our daily vernacular, whether we like it or not, perhaps there is no better time to think about island hopping around the Windward Islands in a privately chartered sailboat? Quite possibly, it is one of the most decadent, socially distant holidays one could fathom. I’ve had the opportunity to sail the Caribbean five times over the past ten years. What exactly was it that always inspired my return? The inherent free-ness of being out at sea, no shoes, no make-up. No washing machines to unload, and no ringing phones.

Nothing but the sounds and sights of nature.

Why Windward?
What makes the Windward Islands so exciting, aside from the wind, is that it is far less touristy than their island cousins to the north. We have sailed the British Virgin Islands in the past, and while beautiful in their own right, they are more crowded with boats and tourists. The Windward Islands, at the end of the day, offer a more off-the-beaten path, and less expected experience in comparison.

Sunsets are spectacular no matter where you find yourself in the Caribbean, whether on land or at sea. I am partial to watching the sun drop into the ocean, waiting for that mythical green flash that always seems to escape me. The sky might be aflame in oranges and reds one night, then purples and cerulean blues, the next. The sea mirrors the color palette, which creates the illusion that your boat is floating on a watercolor painting.

Second Wynn
Our 50 foot, four-cabin catamaran, Second Wynn, rented for the week through Moorings Charters, was a lovely new boat with all of the bells and whistles one would want to spend idle time on the open seas.

Second Wynn had a semi-circular, cushy banquette seating for sunset views, a built-in grill, and various nooks and crannies to watch the world go by. What it didn’t have, much to my daughter’s dismay, was Wi-Fi. Occasionally, we would catch her or her friend teetering from the edge of the boat, trying to capture another boat’s signal. Teenagers at sea.

The cabins were clean and airy, letting in breezes when we needed it, and keeping out the sea water when we didn’t. Each cabin had an en-suite bathroom, again clean and airy (at least until my kids arrived). As with many sailing trips, 99% of waking hours were spent outside and on deck, whether at the bow, where we could sit on the tip of the cat watching the islands pass by, or on the upper deck, above the saloon, to catch the captain’s view. Multiple cozy outdoor areas were found for sun or shade, to read, meditate, or even nap.

Our fearless captain
At 60 years old, with the looks and body of a man half that age, George, our fearless captain, was a man of few words. Very. Few. Words. Yet, while silent and composed, I felt safe in his care right away. He never looked fazed, or shaken. Our first sail, from St Lucia to St Vincent, was quite choppy, but he never batted an eye. This is a man who has seen it all in his 40+ years at sea. These conditions, to our seasoned St Lucian, were child’s play. How did I know that? Well, I asked him.

Untouched and untamed
After we had the first sail behind us, 28 bumpy miles from St Lucia towards St Vincent, most of our days were 3-5 hour journeys. Just long enough to sit back and watch the sea for dolphins and whales, ogle at the passing yachts, or close our eyes and let the sound of the wind against the sails send our minds elsewhere.

Tall, snow white masts in all shapes and sizes rolled along in the turquoise colored waters. An archipelago of islands, with mighty volcanic peaks, and black and white sand beaches alike, could be seen in the distance. Untamed, palm-lined shores, and surprisingly lush green hills that could have been mistaken for the English countryside. True, understated, and untouched beauty. Islands in the foreground created layers of color against the ones in the distance.

Once we stopped for the day, it was mayhem. The kids immediately jumped from the deck into the Caribbean Sea, then continued to do so on repeat for several hours. Some of us grabbed the snorkel gear and started the daily search for colorful sea life. Others grabbed a much-needed beer, an oversized flamingo float toy, and lolled around the perimeter of the catamaran. Leisurely moments, for sure.

First stop, Bequia
Bequia is an unspoiled island that rewarded our long journey from St Lucia with a sunset to remember. When we arrived, the sun was still high in the sky, and most (okay, some) of us had forgotten the bumps of the morning. Large white schooners dotted the bay of Port Elizabeth, and little white houses dotted the hillside above. We took the dinghy to shore and had a relaxed dinner on the bay at Fig Tree. A local duo was playing music and singing to the crowd.

Provision stop at Petit Martinique
Each island in the Caribbean possesses its own distinct personality. Uber-rustic Bequia. Under-the-radar glam of Mustique. Private island-as-resort, Petit St Vincent, were a few that we moored at along the way. Even our hour-long water stop on Petit Martinique shed light on yet a different island vibe altogether.

The local life of the islanders on Petit Martinique, this seemingly un-touristy speck in the ocean, was simple and peaceful. When we walked to the local grocer, Doris’s, to stock up on provisions, the dirt roads led us past school kids rushing to class. Smiling fruit sellers had their goods laid out on blankets, curb-side. Goats roamed freely. It was a side of the Caribbean that had eluded me in the past—a part of me wanted to stay put.

Doris’s, we were told, was the gourmet provisions shop of Petit Martinique. It looked like a shack in need of a major facelift, rickety shelves, caving walls, and no rhyme or reason to the aisles. Yet, it surprisingly stocked everything from Cadbury’s chocolate and Pringles, to imported cheeses and Stacy’s pita chips (all at astronomical prices, of course).

Chic Mustique
Many years ago, my husband and I sailed to Mustique with his family. We happened upon what we later discovered was the well-known beach bar called Basil’s. We had been wanting to return ever since. Known around the globe as the go-to island for celebrities and jet-setters, it couldn’t have looked more unassuming. This is likely because most of the island consists of private homes and villas that are artfully hidden in the overgrown green hills. The island boasts only a handful of boutique hotels.

On the pretty, white sand beach of Britannia Bay, Basil’s redefined the genre of beach bar chic. Built of wood and bamboo, and hovering over the water on stilts, with mismatched stools and comfy couches, we naturally had to spend a few lazy hours there.

The day we sailed to Mustique though, Basil’s was unusually quiet. The boys paddle boarded between the boat and shore, and played a game of cricket. The girls took selfies. We ordered a bottle of wine and took advantage of a quiet moment on land.

Just across the bay from Basil’s, an array of ultra-colorful, rickety fishing boats were piled upon each other, junkyard-style. Each one in a worse state of disrepair. A stark contrast to the brand new sailboats and yachts anchored in the bay. An insta-ready fruit and vegetable stand, made from a repurposed fishing boat, stood off-shore. Snapshots of leisurely Caribbean life.

Later that night, we left the kids on the boat with George and headed up the hillside to Firefly, one of the boutique hotels on the island. The dimly lit and intimate plantation-styled bar and restaurant was quite a change from our low-key dinner at Fig Tree. One of the best parts of sailing to a different island each day was discovering how unique each really is, some high-end and luxurious, others beach dive-chic and gritty.

We hovered above the bay, twinkling lights in the open-air dining room, as well as in the sky above. The tiny, seven-person, circular bar held an eclectic group of characters. Washed up novelists? British ex-pats? It was all a part of the charm—I imagined that Ernest Hemingway would have felt right at home at Firefly’s old wooden bar.

Beach lobster at Tobago Cays
A quick and breezy three-hour sail brought us to a cluster of five mainly uninhabited islands called Tobago Cays. One of the Caribbean’s most biodiverse spots, it had shallow, sandy bottomed bays, unbelievably clear blue water, and extensive sea life. The cays can only be reached by boat, which doesn’t make it all that much less crowded. Tobago Cays may be hard to find, but the secret is out, and everyone wants in.

It was another instant highlight, however, as we jumped from the boat with our snorkeling gear and spent a few hours under the ocean’s surface, searching for sea turtles.

The fish were abundant, and dazzling, the ethereal and iridescent colors made even more vibrant due to the overhead midday sun. The seagrass beds beneath us are the feeding and nesting grounds for a variety of turtles, Green, Leatherback, and Hawksbill, that quietly roamed the sea floor. Every few minutes their massive bodies floated to the surface for a breath of air, then effortlessly descended again. We tracked a mother and her baby for a while, struck by how prehistoric they looked, and how peaceful their lives were.

Pop-up Lobster
Dinner at Petit Bateau beach in Tobago Cays delivered yet another altogether unique food experience. Fifteen pop-up kitchens, each with its own local cook, gas grill, recipe, and personality, competed for our order. While the menus were pretty much identical: tuna, chicken, or lobster, the spiny lobster, hands down, was the reason for coming. Period.

Caribbean Spiny Lobsters, surprisingly, have no claws. But we didn’t miss them. The lobster was grilled to perfection in an array of spices that most definitely would have been a handed down family recipe from our Tobagonian cook. Not surprisingly, he was highly recommended by our captain, who received a free two-pounder in return for his business. Caribbean connections.

The atmosphere was as beach dive-y as it comes. Picnic tables were scattered about on the sand between the palms, with mismatched plastic tablecloths, and intermittently lit strings of firefly lights dangling above. Every so often they glitched, leaving us, momentarily, in complete darkness.

It was BYOE (Bring Your Own Everything). Really, everything—cups, cutlery, drinks, water, wine. What we didn’t have to bring were plates, shoes, or even clothes. We ate in bathing suits with bare feet, not even having showered from our day swimming with the giant sea turtles.

Iguanas and crabs scuttled across our toes and around the beach. Manta rays and pufferfish hovered at the shoreline, greedily awaiting scraps from the grills. The air practically tasted of barbecue, the atmosphere was inherently festive. There we were, a speck on an atoll in the Caribbean, enjoying a lobster that just might have spoiled me for life. At the risk of sounding hyperbolic, it was one of my favorite dinner experiences. Ever.

Moving on up to Petit St Vincent
The lobster night at Tobago Cays seemed like an alternate reality when the next morning, and just a few hours’ sail away, we discovered the island oasis of Petit St Vincent. PSV is a 115 acre island resort with 22 secluded stone cottages, two yoga studios, a Balinese spa, a dive center, an open beach bar, and two restaurants.

I read that PSV has the honor of being the Caribbean’s first boutique hotel. An ultra-luxury low-impact resort, we could barely see the cottages from the beach. Bikes dotted the island, so guests could just grab and go. No wi-fi, telephone, or TV added to the secluded escape-from-reality vibe. Room service, I was told, was summoned by raising a flag at each cabin’s flagpole, which then arrived via Mini-Moke, the ubiquitous transport of the island.

We played beach cricket at PSV, and then opted for an impromptu lunch off the boat at their beach restaurant, Goaty’s. Fresh tuna, sea bass, and bean burgers, were a much welcomed alternative to our daily scramble of  ‘create your own lunch with whatever we have left on the boat’. We ordered more than our fair share of food and rosé and then swam to the catamaran, stomachs full and happy.

Snorkelers paradise at St Vincent
With our vacation days quickly running out, we sailed north, and back towards St Lucia. The lush, green coast of St Vincent came into view, and ended up at a desolate bay called Petit Byahaut. Captain George said it was the best snorkeling in the area. Who were we to disagree?

I am not the most adventurous snorkeler, but the sea life in this bay was beyond anything I’d ever seen. Towards one end of the black sand beach, was an underwater wall, at least 40 feet deep, of coral, trumpetfish, urchins, eels, and needlefish, to name a few. It was as if I had snorkeled up to the glass wall of an aquarium. I dived as deep as I could for some precious hollowed out sea urchin shells, splitting my eardrums apart as I did, then accidentally dropped my treasure. I guess they belonged to the sea, anyway.

For once, I was without a camera, and I couldn’t document the underwater natural beauty in front of me. It forced me to see more clearly, to be fully present and in the moment. (I did, however, spend a moment cursing myself for not having an underwater camera.) I committed that day of snorkeling to memory, which was better than any picture I could have taken.

Coming full circle, St Lucia
After a week of surprises, culinary adventures, crazy seas, and gorgeous sunsets, we finally ended the trip where it all began, the bucolic bay of Sugar Beach, in St Lucia. The resort, where we had spent five nights prior to our sail, was a welcome sight with its white, plantation-style cottages nestled gently in the hills. We had come full circle.

With about twenty minutes left to sail towards the Pitons of St Lucia, George shouted, ’dolphins on the bow!’ I was stunned, it might have been the longest sentence he uttered in seven days. Dolphins had eluded us the entire week, but now, a mommy and baby dolphin decided to escort us back to the calm harbor of St Lucia. I joked that George had ordered those dolphins as a final gift to us for our intrepid week under sail. A week of minimal clothes and maximum memory building. It had ups and downs, both literally and figuratively, and it made for fantastical and funny stories.

Windward, Ho!
What’s in a name? Well, as it turns out, a lot. We were looking for a more authentic sailing experience, with wide open seas, a lot of wind, nature, untamed wildlife, and a huge heaping of the unknown. We were hoping for the kind of vacation that would take us away from reality, with just the right balance of adventure and luxury. We got it all.

Twenty years from now feels like a long way off, but I’m not taking any chances. Here’s to fair winds and following seas.



Jamie Edwards is an avid traveler, travel writer, and photographer. She launched I am Lost and Found, her adventure/luxury travel website after 25 years of living and traveling around the globe. Jamie’s goal is simple: to inspire travel.

Keep up with Jamie’s adventures in travel here.

CIRE Travel is a full-service travel agency headquartered in New York, NY.  Our expert team supports clients across the country and around the world.

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