Skip to main content

Cowboys in The Caribbean

Six weeks before we took off for St. Lucia, my nervous father texted me, “I’m buying some new clothes for the trip. Will I be okay in T-shirts and quick- dry tops?” “Sure!” I replied, “Think about buying some linen, too.” “Linen?” he texted back, “where on my body and where on a boat would I put linen?”

Six weeks before we took off for St. Lucia, my nervous father texted me, “I’m buying some new clothes for the trip. Will I be okay in T-shirts and quick- dry tops?” “Sure!” I replied, “Think about buying some linen, too.” “Linen?” he texted back, “where on my body and where on a boat would I put linen?” 

Thus began the education of my father, Mark, a life-long Westerner who was about to embark on his first-ever sailing trip—leaving his bolo ties and cowboy boots in Colorado to giddy up with my mother, Julie, (a Wisconsin native who grew up sailing) to St. Lucia for a week of chartering with me and my friends.

Upon our arrival at The Moorings base in Marigot, St. Lucia, we found Fair Pointe, our Moorings 4300 catamaran, already polished and provisioned. “Remember to fill up your water bottles and charge your electronics,” I reminded the crew. “This is the last time we’ll have shore power all week.” The fact that my parents didn’t sprint to the nearest resort, even after realizing they were about to spend a week on a 42ft boat in 110-degree heat with six 20-somethings and no AC, showed just how committed they were. With a smattering of clouds and a pleasant breeze, we set sail for our first destination: Soufrière, St. Lucia.

Sailing south along St. Lucia’s west coast, I looked up from the helm to see my parents seated on the bow seats, their faces bathed in sunlight as they watched the lush green hills go by, grinning like a couple of kids. Later, grabbing a mooring near Soufrière, we spent the afternoon swimming and kayaking amidst some of the finest marine life we would encounter all week. Right beneath our boat we spotted vibrant coral gardens, eels and fish, while above us the dramatic Pitons reached up 2,500 feet into low clouds. 

Lying on the trampoline that night, my first mate, Matt, and I got to know those Pitons well. Too excited to sleep, we peered at them for hours, waiting for the sun to rise behind them so we could set sail for the Grenadines. At 0530, dawn finally crept over us. We revved our twin engines and headed south-southwest, leaving St. Lucia in our wake. 

I’ll admit it: we could have eased my folks into the charter experience a bit more gently with, say, some island hopping in flat water. But we were determined to experience both St. Lucia and the Grenadines in one fell swoop, and that required an 80-mile slog in both directions. As luck would have it, just before our arrival in the Caribbean, the usually reliable easterly trades shifted south, serving up 12-14 knots directly on the nose. Let the adventure begin! The most treacherous stretch was between St. Lucia and St. Vincent, where weather and water pass uninterrupted between the Atlantic and the Caribbean. The seas were rolling, the air was hot, and my poor father spent a couple of hours making, as he put it, “sacrifices to Poseidon.” It took nearly three hours for St. Vincent to appear over the horizon, and another three to raise Bequia. But we kept our spirits up with help from the soundtrack to Pirates of the Caribbean, which was filmed here. 

The cruising guides said that Bequia had the easiest customs in the Grenadines, so we turned into Admiralty Bay, dropped our sails, started our engines and promptly began spinning in circles. Evidently, our starboard engine was dead, leaving us only the port engine to maneuver with. Fortunately, some creative steering got us to a mooring with a minimum of drama, and we moved right along to Mark and Julie’s next lesson in chartering: Caribbean engine repair. 

The Moorings’s Bequia contact was away for the off-season, so we dinghied ashore and asked the first person we saw for help. He, in turn, called up Kerry Ollivarre, the Good Samaritan of Bequia, who met us, came aboard, got his hands dirty, and $50 and 30 minutes later, went home to his wife and family. Crisis averted. Afterward, we went to dinner at Tommy Cantina, ordered rum punch and fresh-caught barracuda and toasted Kerry, whose no-worries attitude reminded us that in the islands, it’s all good, mon.

“Batten down the hatches! Squall on the horizon!” Matt called from the helm. The crew looked up to see a fast-approaching downpour filling up half of the sky. We were only 10 miles from the Tobago Cays and Rainy Season had picked that moment to rear its ugly head. The squall line drew closer and expanded, pounding the open water before us and swallowing one island after another. There went St. Vincent, then Mustique, then Bequia. We held our course, hoping the storm would depart as rapidly as it had arrived. There went the Cays, and suddenly we were in the middle of a veritable deluge. My father brought out the soap and lathered up in nature’s fresh-water shower, laughing at his own cleverness. 

The entrance to the Cays is narrow and winding, and we had little idea what would be on the other side. Utterly drenched, and still sweating, Matt and I looked at each other—nervous but resolute—and opted to drop the sails and motor in. The entire crew kept a sharp lookout for boats, rocks and channel markers. 

Sure enough, the rain began to lift just as the channel came into sight. By the time our stern cleared the channel entrance, the squall had passed, and the lookout crew was now stacked up at the bow, beaming in awe of the scenery before them. 

The channel opened into a wide anchorage encircled by a string of small white-sand-and-coconut-tree islands. There were only three other boats on moorings—ah, the joys of the off-season!—and the only sign of civilization was a torn volleyball net on a nearby beach. We wasted no time plunging in, then hiked up, over and around each of the five Cays, swam with sea turtles, and played in the waves on a peninsula where the Caribbean Sea crashes against the Atlantic Ocean. We kayaked and snorkeled, and even did a little kiteboarding on the flat water in a now-perfect easterly. 

“You know, this feels a lot like summiting a fourteener,” my father said, referring to those Coloradan peaks with altitudes greater than 14,000 feet. “We spent two days in rough seas with unfavorable breezes, we made sacrifices to Poseidon, fixed an engine, braved a squall and finally arrived at this, the Tobago Cays, the summit.” 

Clearly, he was catching on to the whole sailing thing. 

That night we found ourselves enveloped in a canvas of southern constellations many of us had never seen before. As we gathered on the trampoline, Matt brought out his guitar, and he and my father took turns leading the crew in songs—Old Crow Medicine Show, Hank Williams, the Dead, Donovan-—songs that reached across generations. They were songs we’d sung a hundred times before, but for some reason, “Don’t Think Twice, It’s Alright” took on a whole new meaning beneath those Tobagan stars. 

“Hey mon, where you headed tonight?” A band of boat boys met us at the end of a perfect sail between the Cays and Mayreau. This was nothing new for the Grenadines, and we kindly waved them off as we continued our approach into Salt Whistle Bay. 

“Hold on mon! I’ve got good news for you!” they said, and for once, I was glad they persisted. The leader introduced himself as “Black Boy” and congratulated us on having arrived on the first of September: the first day of lobster season. He then invited us to his beachside hut for dinner, where we feasted on fried plantains and huge, juicy lobsters alongside a group of charter guests from France. When the language barrier became insurmountable, we resorted to the international language: music. Black Boy’s thick reggae tones rose above the beat of his friends’ drums while French and American sailors danced and laughed the night away. 

The next morning, we left that slice of paradise and sailed 12 miles north to Mustique. The wind from the east blew a steady 10-12 knots, and schools of porpoises and flying fish leapt from the waves around us, trying to catch a glimpse of our salty crew.

After the gritty towns of Bequia, the isolation of the Tobago Cays and the rustic feel of Mayreau, Mustique was quite the surprise. The island has been privately owned by a small circle of wealthy Brits (including Princess Margaret) since 1958, and they keep it looking like an old English manor crash-landed in the Caribbean. Perfectly manicured lawns lined the driveways to the homes of LaCoste, Tommy Hilfiger, David Bowie and Mick Jagger, to name a few. A local taxi provided a tour of Macaroni Bay, several massive estates and one darling town. We moored in the harbor for a pretty $68 (I suppose that’s the price of luxury) and called it an early night in preparation for our big day. 

For the third time that week, we set off at first light. As we headed north toward St. Lucia, the wind turned with us and served up another heaping dose of windward sailing that left Dad conversing with Poseidon. 

“Every time the Pope lands back in Rome, he gets on his knees and kisses the ground.” My father was still green, but grinning and continued, “I look forward to that.” I could tell he was embracing the joys of sailing.

Ironically, by the time we made it to the restaurant on Anse Chastenet in St. Lucia, the entire crew was so accustomed to the water, we had to hold onto the bar to keep from falling over. As we watched the sun set over the Caribbean Sea I finally dropped to question to my folks: “So, what did you think?” 

“It’s a bit like camping,” they said. “Everyone sleeps in close quarters. You’re a little dirty, a little salty, and always aware of how much food and water you’re consuming. You wake at the crack of dawn and get abused by the elements until you’re ill, all while living cheek-to-cheek with seven other stinky people.” 

“And would you do it again?”

“In a heartbeat.”


Where to go

St. Lucia: anchoring in Soufrière can be tricky. The Pitons, the rainforest and volcano are among the island’s great sites; Bequia: Port Elizabeth is the easiest and nicest place to clear customs in the Grenadines. Admiralty Bay is full of good restaurants and a nice market for provisioning; Mustique: customs is at the airport, the island is expensive but worth visiting for people watching, estate-gawking and beach combing; Tobago Cays: The area is a protected marine park, so expect to pay Park fees. The wildlife is unmatched; Mayreau: Salt Whistle Bay has a great beach and club and the anchoring is ideal. There are not many provisioning options 

When to go

Wet season lasts from June through October, when rain is more common. Luckily, these islands are far enough south that hurricanes are rare


The breeze blows consistently from the northeast to the southeast at 10 to 25 knots, perfect for one-way charters between St. Lucia and Grenada

Cruise Guides

2009-2010 Sailors Guide to the Windward Islands by Chris Doyle, 14th Edition

Charter information

The Moorings has bases in St. Lucia, St. Vincent, Canouan and Grenada;



The Extraordinary Life and Mysterious Disappearance of Thomas Thor Tangvald

The first boat Thomas Tangvald ever owned was just 22 feet long. She was an odd craft, a narrow plywood scow with a flat bottom, leeboards on either side, and square ends—little more than a daysailer with a rotting deck and tiny cabinhouse tacked on. Thomas paid just $200 for more


USVI Charter Yacht Show Showcases a Flourishing Industry

As the U.S. Virgin Islands continues to attract sailors seeking to charter and explore the pristine territory on their own, the immense growth and expanded options for a crewed yacht or term charters have exploded here over the past five years. Last week, the USVI Charter more


Personal Locator Beacon Wins Top Design Award

The Ocean Signal RescueME PLB3 AIS Personal Locator took top honors at the 2022 DAME Design Awards, while Aceleron Essential, a cobalt-free lithium-iron phosphate battery with replaceable and upgradeable parts, won the first DAME Environmental Design Award. Announced each year more


EPIRB in the Golden Globe Race

Tapio Lehtinen’s boat sank early this morning southeast of South Africa while racing the Golden Globe Race, a faithfully low-tech reproduction of the 1968 Sunday Times Golden Globe. The boat went down quickly and stern-first according to the skipper’s emergency transmissions. more


Victory, Tragedy in the Route du Rhum

The 2022 Route du Rhum was a highly anticipated event in the ocean racing calendar, but few could have predicted exactly how challenging, dramatic, and tragic it would ultimately prove. French yachtsman Charles Caudrelier took home gold aboard the Ultim maxi trimaran Maxi Edmond more


Boat Review: Lyman-Morse LM46

Lyman-Morse has been building fine yachts in Thomaston, Maine, ever since Cabot Lyman first joined forces with Roger Morse back in 1978. With experience creating and modifying boats built of various materials, backed by its own in-house fabrication facility, the firm has more


Know-how: All-new Battery Tech

Until very recently, the batteries in sailboats used some form of lead-acid chemistry to store energy. Different manufacturers used different techniques and materials, but in the end, the chemistry and the process by which the batteries charge and discharge electricity remained more


At the Helm: When Things Go Sideways

I don’t like sea stories. My number one goal on every passage is to get the crew back in one piece. My number two goal is to get the boat back in one piece as well. If I can’t do both, I’ll take the former. Do this long enough, though, and things are going to happen, no matter more