Relaxing on choppy waters
At the Bitter End, some of the world's best sailors take amateurs - including many entrepreneurs - on a wild ride.
VIRGIN GORDA, BRITISH VIRGIN ISLANDS (FORTUNE Small Business) -- If sailing is relaxing, then this is not sailing.
At the moment, Rich Rowley, CEO of Design Arc, finds himself onboard a 24-foot boat, careening into a wave-whipping southeast wind, sails at full strain, the hull tipped up toward the far horizon, and four knife-prowed yachts bearing down at full speed. But this is exactly what he signed up for when he decided to spend his 50th birthday in the British Virgin Islands.
Rowley runs a design and construction firm with his wife in New Canaan, Conn. He directs residential architectural projects, from half-million-dollar renovations to from-the-ground-up jobs worth $2.5 million. He juggles a half-dozen projects at once and handles four times that many contractors on a rotating basis.
But Rowley also sees himself as a sailor, and an obsessed one at that. So when it came time to relax, he jetted off to the warm, sun-dappled waters of Virgin Gorda and traded one kind of stress for another.
Racing gets tense fast, even when you're on vacation. Rowley and the four crew members are now crammed on the edge of the cockpit, using their weight to keep the boat from capsizing. Then the gust shifts.
"Bring it in! Bring it in!" shouts the skipper, Rod Johnstone. Quick changes in wind necessitate quick thinking, but Rowley, sitting to Johnstone's left, clutches the mainsheet hesitantly. "Bring in the friggin' mainsheet!" Johnstone finally roars.
Rowley pulls, ratcheting in the mainsail. The lead boat that's spearing toward our midsection feints to its right and slips past, inches behind our stern. In a mad scramble of bodies and ropes, the boat turns into the wind. The sail flaps, then shudders and tightens as the wind fills it on the opposite side. They've done it: They're around. And without a scratch.
Rowley and the crew have congregated here for the Bitter End Pro Am Regatta. Now in its 21st year, the annual five-day event allows amateurs and even beginners to sail with 10 of the sport's most famous names. While many vacationers come here simply to relax, the Pro Am Regatta is about competition in its keenest form and the rare chance to breathe the same air as top professional sailors. It's less about the sailing than about the participants' fascination with sailing gods, even if the regatta entails being ordered around by them.
"You're sailing with legends," Rowley says. "These guys are Olympians, America's Cup skippers. They're at a whole other level." For Rowley, partnering with Johnstone (the inventor of a revolutionary racing yacht called the J24) is like sharing a racecar with Enzo Ferrari.
Sprawled along a mile of coast on the eastern edge of Virgin Gorda's North Sound, the Bitter End offers some 20 varieties of boats (including sailing dinghies, catamarans, and motor launches) free for guests to use whenever they want - an amenity that makes up for the beach-cottage furnishings, humble compared with other resorts in its $4,200-a-week price range.
"We're old-school Caribbean," says general manager Mikhail Shamkin. "We're not brass and glass." (All the same, the resort recently renovated 30 of its oceanfront suites with Italian-marble-tiled bathrooms and teak vanities.)
The original Bitter End was no more than a clutch of bungalows when the Hokin family, wealthy industrialists from Chicago, discovered it in the course of their frequent cruises around the British Virgin Islands. The lodgings might have been modest, but the setting was spectacular: right on North Sound, an aquatic amphitheater blessed by calm waters, clear skies, and steady, strong winds. The Hokins liked the place so much that in 1973 they bought it. Since then they've transformed the Bitter End into a hideaway for avid sailors like themselves.
The Pro Am Regatta began after the resort absorbed an adjacent property and was looking to publicize the expansion. Marketing director John Glynn invited some leading skippers for a week of low-key match racing in exchange for free room and board. He didn't think of involving guests in the race, but so many expressed interest that room was found aboard the racing boats. Now any guest staying at the hotel during Halloween week may take part.
The racing day starts at 9:30, when a launch ferries the skippers and amateur crew members out to the sailboats. (Four races, each about 20 minutes, make up a session.) Unless crew members are exhausted - which they often are after a few days - they go out and race again after lunch.
Eighty minutes of sailing might not sound like much, but racing can be ferociously intense, both physically and mentally. Competition demands fast decisions based on ever-shifting assessments of wind, currents, sail settings, and opponents' boats. And it takes real leadership skills to weld a group of strangers into a team.
For Rowley, the experience is more like being an employee, one who has to jump - or tie off a rope - when the boss says so. Going from chief executive to crewman is quite a shift, but Rowley loves the excitement.
"These pros," he says, "they don't back down. Once they're in their boats, they're in it for the kill."
Many Pro Am participants are entrepreneurs. Johnstone, for instance, started out by building a sailboat in his garage. The design proved so light, affordable, and fast that J Boats is now a leader in its field. Another pro, Lowell North, founded a sail company whose products are used on 80% of the world's racing boats. Keith Musto, the foremost British dinghy sailor of the '50s and '60s, has grown his line of waterproof sailing gear into a worldwide clothing brand.
The last day of the regatta dawns picture perfect: blue skies, a moderate breeze, the flat sea ruffled here and there with dabs of foam. Once again Rowley's job is to work the mainsheet - important because it controls the efficiency with which the mainsail catches the wind. Before the race gets underway, Johnstone steers the boat near the starting line, offering Rowley tips. But the pace quickly builds, and soon they are dodging back and forth amid a chaos of boats, each maneuvering for optimum position before the start whistle. Then they're off, six boats neck and neck like horses in a chariot race.
As the race proceeds, Rowley's work on the mainsheet improves considerably. Having learned to anticipate the correct setting of the sail, he settles into the taut rhythm of the now practiced crew.
But it's not enough. Because of the vagaries of the wind, coupled with perhaps a few strategic errors, Rowley's boat finishes ninth out of ten boats in that race, and dead last in the next. On the third, they hold it together well enough to claim seventh place, but on the fourth and final race they're dead last again.
"Nice work, everybody," Johnstone says, drifting past the finish line. "We didn't do too well, but that's my fault. You guys sailed great."
Rowley takes his team's performance in stride. "It was fun to learn and fun to be there," he says, although he hints that if he comes back next year he might sail on a different boat, one likelier to offer a taste of victory.
Off the water, the customers are no longer crew members to be barked at, but honored guests. A few of the younger skippers are aloof. But most of the pros are low-key and modest - happy to come down for free, just to enjoy the locale and the company of their tribe. Johnstone says he doesn't mind having to deal with amateurs in the cockpit.
"We're here to make it fun for the paying guests. We're not here to compete," he says. "We're all promoting sailing. That's the bottom line."
Come nightfall, everyone gathers for a cocktail party and awards banquet. There are increasingly drunken thank-you speeches and expressions of mutual admiration between the elder champions who built the sport and the young stars out there winning the America's Cup and Olympic medals today.
For the amateurs, the regatta is a rare opportunity to bask in sailing's most exalted brotherhood and a chance - at the end at least - to relax. By the end of the evening, Rowley has had a few cocktails and is several shades of sunburn redder than when he arrived at the beginning of the week. In fact, he looks as if he needs a vacation from his vacation. But his smile couldn't be more real.
"I'm exhausted. I'm wiped out," he says. "Thank God there wasn't more racing. Because I probably would have done it." 
See more Off Hours in our archives:
Little Orlando
Climbing the Amazonian trees
A little visit to Salt Lake City
