TRAVEL — 09 June 2015
St. Thomas offers a regatta for every sailor

By Eric Barton

Destinations magazine

It was near the conclusion of the first race at the St. Thomas International Regatta, and if you ignore a few facts, our sailboat held first place. Within seconds, we would need to make the turn into the harbor on this Caribbean island. The race ended there, and we could nearly see the finish line.

All around us were the lead sailboats. Simple speedsters that cost just a few thousand mixed with multimillion-dollar yachts. Our competitors had unfurled their spinnakers, full of vibrant colors and flying out front like enormous parachutes.

We banked right and slipped into our destination. As the crew readjusted the sails, which were caught in a fierce wind, the fabric flapped like bed sheets on a clothesline. The crew re-released the spinnakers out to the side to catch the easterly wind, and the sails cracked like gunfire.

We would lose some of the wind in the safety of the harbor. Out on the open water, though, it was blowing like a hurricane feeder band. While the sunny sky held nothing but little cotton balls, the ocean looked furious. Hulls crashed through seven-foot swells.

Up ahead was the yellow buoy that marked the end, and yet we were still in first. You could almost swim to the finish.

There are a few things you should know about the boat I was crewing on that day in March. It was a shabby-looking 34-footer, older than most college kids. Its captain had never raced her before. He didn’t even unstrap the kayak on its deck before the race.

But that is what’s special about the St. Thomas regatta. This is a race that allows anybody to compete. Captains who show up in barely seaworthy sailboats take the start line with corporate-sponsored yachts.

St. Thomas is also a place where someone with limited sailing experience, like me, can end up crewing on a competition boat. After finishing a basic sailing class at Broward College, I found myself right there, in the stirred-up seas of one of the Caribbean’s most legendary regattas. St. Thomas is, after all, a destination for anybody interested in sailing, whether it’s watching from the hilly shoreline or riding the rails of a yacht.

An approachable atmosphere is how they like it on St. Thomas. It’s a destination where sailing doesn’t have the pretension of other Caribbean islands, says Lyn Reid, a retired teacher from Detroit who has volunteered in every one of the island’s 42 regattas.

The regatta started as a pet project of the late Walter Fisher, president of Rolex Watch USA and a regular on St. Thomas. He would give away watches to the winners, and the prizes quickly attracted sailors from Florida to South America. Even with all that attention, Reid says the regatta has deliberately shunned the galas that define other Caribbean races. The entry fee, for instance, is just $300.

At the after-party following that first day’s race, Stephanie Giering of Miami says the casual atmosphere is what makes the regatta in St. Thomas one of her favorites. She should know: Her husband, Scott, is a race official, like a sailing umpire, so they go to regattas around the globe.

“The island is so laid-back,” says Giering, sitting on plastic lawn furniture as a guitarist plays reggae out back of the St. Thomas Yacht Club. Most people are barefoot, wearing the race shirts and board shorts they wore on the yachts that day. “Have you ever driven in Miami? This is definitely not that. At other regattas, the sailors are so competitive. Here, look at the bar, they’re buying each other drinks.”

If you’re just getting started in sailing, St. Thomas is a fine place to begin. Several local yachts are available for charter. Captains will stay at the helm or, for the experienced, allow you to take the helm. There are also places to learn the sport. Former U.S. windsurfing Olympian Paul Stoeken recently opened Island Sol, a sailing school that offers classes for newcomers and advanced race lessons.

“This is a place where you can experience sailing by getting out on the water and getting the salt spray in your face for not a lot of money,” says Stoeken, who competed in this year’s regatta. “You can quickly get hooked on this sport. It hits you in the gut, and the people who do it, they live it.”

Here’s a good example of how accessible sailing is on St. Thomas. The island created an entry-level sailboat called the IC24. The idea was to design the stock race car of sailboats, which can be made out of a few different types of boats, reshaped and given new sails, often costing under $20,000. But this is no discount ride. IC24s are nimble, beautiful in their simplicity and easy for rookies to handle.

For my first regatta, things didn’t begin exactly as planned. Our captain made a poor turn at the start line, and we found ourselves sitting into the wind as everyone sailed away. By the time we crossed the start, our competitors were colorful blips on the horizon.

So we skipped the official course and sailed toward the harbor, where the first race would end and where we could line up for the second heat. As we made the right turn into the harbor, we realized that we had ended up in the lead, albeit disqualified.

All around us, a mix of IC24s, monster yachts and small Hobie-style beach cats jostled for the lead in their classes. Brilliant strategies play out as captains try to pull up alongside a competitor to steal the wind, making the other boat’s sails flap uselessly. The right turn into the harbor required cutting around a buoy, and the closest to it had the shortest distance to the finish. There were near collisions as captains scream over the crashing waves that they had right of way.

We ended up in last, considering our shortcut, but we were lined up for race two. All 62 boats gathered in the harbor for the start of the second race, making short circles as close as they could to the starting line. There were just 20 minutes before the second heat, enough time for granola bars and an inspection of blisters from rope running through bare hands.

When the horn sounded to start the second race, we headed out with the pack in a class called “non-rated cruising,” or basically whatever you’ve brought to the regatta. There were only three others in our class, so we began speculating about how we might be competitive this time.

The wind made the start of the second race tricky. It was blowing from the mouth of the harbor. The only direction sailboats cannot travel is directly into the wind, so that meant turning left and right several times before hitting open seas.

Following the lead of other boats, we cut right first, heading straight for a rocky beach. It’s a tack that would require precise maneuvers, a left turn across the harbor, followed by a right turn out to the ocean. We picked up speed, and our aging boat tilted to what felt like 90 degrees.

We were just yards from shore. Shadows in the water off to our right revealed rocks. Any second, we had to turn left and out across the harbor. But our captain, making that mistake we’ve all made before, albeit with fewer consequences, confused left for right. Instead of steering away from the rocks, we headed right for them.

The hull bounced off a rock as if some giant hand had picked us up by the sail. We landed on more rocks, and were grounded. The boat listed, almost sideways as rocks pounded our keel. Waves grinded us into the stones. Checking the cabin for water, I began wondering how wise it would be to jump.

Luckily there’s always a towboat nearby for races, and it arrived in minutes, pulling us from the rocks.

Sure, an early disqualification in the first race and a humiliating trip to the beach in the second is not an ideal way to begin a racing career. But even with all that went wrong, even with a fairly frightening ending on the rocks, I knew this wouldn’t be my last race.

There’s always next year’s regatta.


Broward College 

580 Gulf Stream Way, Dania Beach,; 954-201-4500

Broward College offers an excellent beginner sailing class every Saturday for six three-hour lessons for $169 at Tigertail Lake, that blue stretch of water next to Outdoor World in Dania Beach. Taught by veteran sailor Richard Fial, you’ll learn the basics and a few tips for racing, along with earning a sailing certification.


Lauderdale Yacht Club 

1725 SE 12th St., Fort Lauderdale,; 954-527-2223

The yacht club in Rio Vista Isles offers several clinics for those looking to improve sailing skills, including a beginner racing course, a women’s-only class and a certification in keelboat sailing. You don’t have to join, but you must be sponsored by a member to participate. (Yacht club members get discounted sailboat rentals.)



Ritz-Carlton, St. Thomas

6900 Great Bay, St. Thomas, U.S. Virgin Islands,; 340-775-3333

It’s hard to beat the view of the Mediterranean-style Ritz, which looks out across a sailboat-crowded bay toward the island of St. John. The Ritz is steps away from the St. Thomas Yacht Club and near several charter services. Rooms start at $600.


Gladys’ Café

Royal Dane Mall Shopping Center, Charlotte Amalie, 340-774-6604

Tucked in the narrow cobblestone alleys of the historic St. Thomas city of Charlotte Amalie is the equally quaint diner Gladys’ Café. After a morning on the water, lunch on dishes including curry chicken, buttered conch or the local specialty, triggerfish.


The Clipper Independence

American Yacht Harbor,, 340-775-1408

Charters abound on St. Thomas, and the 44-foot clipper Independence is among the most popular. Full-day rates run $140 per adult, or book the whole yacht starting at $600. Ask for a hands-on experience where you will take the wheel and sails, or stretch out on the deck and relax.

Where to Go on the Water

Winds that whip off the Atlantic keep St. Thomas an ideal sailing spot year-round. Perhaps the best part of sailing here are the destinations, including secluded coves and nearly abandoned beaches you can make yours for the day. The often-crowded Magens Bay features views of the St. Thomas mountain, a beach with sand the color of linen and waters every shade of blue. For a quieter spot, sail 30 minutes to the island of St. John’s stunning Honeymoon Beach.


Destinations is an annual travel supplement of the Sun Sentinel, produced by City & Shore Magazine

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