When people think of the Caribbean, they envision sun, sand and swaying palms. Because of those alluring attributes, the region has become a magnet for sailors and all things “sailing.” Almost every island now hosts at least one major sailing race or regatta and some of them are downright HUGE!

St. Marten’s Heineken Regatta this year drew nearly 300 entrants. The Stanford Antigua Race Week choreographed 185 boats as they sailed around the island. In April, one of our favorites, the Antigua Classic Regatta, attracted over 60 of the world’s most glorious old “gals” ... and one old “guy.”

Bruce’s art show schedule placed us and our boat, Woodwind, in a ringside seat one week before this year’s Classic got rolling, at the entrance to Antigua’s Falmouth Harbor. Everyday we watched the horizon as tiny, distant dots slowly grew into familiar sail configurations of schooners, sloops, cutters and yawls. They came in all sizes and shapes, from Adela’s 147 feet of gloss and gleam to the newly launched 24-footer, Springtide, sporting a fresh coat of British red paint. The J/boats, Velsheda (130 feet) and Ranger, (136 feet) arrived towering over all, with masts that seemrd to touch the sky. There were a few “plain Janes” among the fleet, but most of the boats were so highly polished and varnished sunglasses were mandatory just to walk the docks.

All sailing events in the Caribbean have two time consuming components: races and parties. Like cookies and milk, you can’t have one without the other and they never seem to even out. So, holding to that adage, the Antigua Yacht Club began the festivities with a launch celebration for two new nautical books by Alexis Andrews, the island’s premier photographer. Andrews is the proud owner of one of the eight boats that showed up to race in the Traditional Class. Seven of them were built on the island of Carriacou and the man who gave them life, Alwyn Enoe, sailed in for the debut of the books that celebrate his craft and talent. In “Vanishing Ways,” Andrews tells the colorful story in words and photos of Carriacou’s boat building past. The second book, “Genesis,” chronicles the building of Andrew’s own sloop, including some serious superstitions and a sacrificial goat.

With 60 boats entered to race and each needing upwards of 10 crew members, I figured I could find a ride and a story. I first imagined I might join one of the J/boats, until I heard the small delivery crews would be beefed up by dozens of Olympic athletes flown in for the event. When I saw their hulking bodies board for a pre-race practice, I started looking elsewhere. The Carriacou boats, my favorites, were appealing. One 50-foot schooner was desperate for crew, so I had options! But when Lone Fox pulled in and owner Ira Epstein welcomed me aboard, I knew my search was over. At the end of last year’s Classic Regatta, Ira expressed a desire to race again with the same crew and, amazingly, eight of us showed up. The 10 who couldn’t make it were replaced by an ocean of experienced sailors, and together we represented nine nations.

Day one, everyone reported for duty at eight sharp. Everyone except the stragglers who witnessed the finale of Mt. Gay’s lethal Red Hat Party (buy three rum drinks, get a free hat). Thankfully, no hats were in sight, but there were plenty of red eyes, which started our daily pre-race ritual of late-night true confessions. No doubt I was with a polished party crew. As we readied the boat and cast off from the dock, half a dozen standby wanna-be crew dejectedly wandered off. Ira passed out Lone Fox hats (the shirts, stuck in customs, would come later) and we received our assignments.

The seas off Falmouth Harbor were jumpy and confused, which sort of matched our moves as we sailed our first rehearsal 45 minutes before the start. Ira and first-mate Guillaume Touhadian, accustomed to handling the ol’ girl alone, gave instructions and directed us toward gear until our tactician, Mad Dog Mark St. John, put us on the line for a near perfect start. The “Old Road” course gave us a chance to get to know the boat. We popped the chute once, but heavy winds kept the mizzen stays’l in the bag. Mistakes were made all day: clumsy tacks, sail trim slow, too many cooks stirring the stew. But what felt like a practice turned out to be the number two spot when we finished right behind the 65-foot beauty, Rahda.


Left to right: Ema Heard, Mad Dog Mark St. John, Aine Hanery, Ira Epstein.

Memories are made at the Classic and ours came early on race day two. Five minutes before the start Lone Fox was maneuvering off Black Point. Fluky winds forced three boats
dangerously close to each other, with negligible steerage and little weigh on. Like a movie in slow motion, we watched as Radha’s bow swept inches from Lone Fox’s belly, moving back … back … back … until finally hooking the mizzen rigging, ripping it and half the boom away. My two aft-deck companions and I hit the deck as ropes, splinters and some loud obscenities rained down.

Ira was trying to drive us away, but the two boats were attached by a line from our mizzen, wrapped hard on their bow anchor. Long seconds passed with no knife in sight, until finally the boats parted. Ira and most of our crew thought we were done for the day, but Mad Dog and our weather guru, Gerry Robertson, coached him toward the start. Hands and bodies worked furiously to lower the flogging sail and tame the dangerous debris. The starting gun sounded and we hit the line with Radha hot on our tail.

The “protest” word started flying around. Will we? Should we? But Mad Dog reminded everyone, “It’s a gentlemen’s race. Let’s just out-sail ‘em. Besides, you have to give the committee a case of champagne when you file. We’d rather drink it ourselves, right?” The man’s a genius. Right!

Gerry added, “We don’t need that mizzen anyway.” And I guess we didn’t, because we finished the race in first place, minutes ahead of Radha.

Back at the dock we pulled off what was left of the boom, sent it packing to the woodworker’s shop and headed to the Pimm’s party to re-live our harrowing event … complete with embellishments, of course.

Three parties later, we were back on board in the morning, strapping on the bandaged boom to sail the spectators’ Cannon Course. Twenty-four miles of reaching back and forth, boats passing dramatically close, cameras flashing in the hot sun. A fleet favorite was a porky old gaffer named Old Bob, and each time we crossed paths it was obvious that, although they were slower than skaditch, they were the party to beat. Lone Fox crossed the line, collecting another first, and we readied the boat for the proper Parade of Classics, past the reviewing stand in English Harbor.

The waters around Antigua are full of lobsters, but the state of Maine (the state!) flew in their own to cook up a cauldron of lobster bisque for a raucous crowd of hundreds. That event segued into the Laurent Perrier Champagne party and we all had to agree … the racing schedule was exhausting but the party agenda almost killed us.

Race day four dawned with a deluge that filled dinghies and washed away the sins of the night before. Wet crew shirts were shrouded with rain gear and garbage bags. The VHF weather report sounded bleak; more rain and six knots that might fill in. Might not. We joined the group of slatting sails on the course, listening for word from the gentlemen on the committee boat. They were fielding a barrage of goofy questions until they simply had enough and we heard, “We will not make another announcement for 40 minutes. Over and out.” True to their word, those minutes ticked by until finally the radio came to life and announced, “The race today has been cancelled!”

After a few fake, “Oh, that’s too bad,” remarks, we all jumped around, high-fiving each other, knowing we were winners. Ira and his Lone Fox were victorious.

Hard to believe, but four days of racing and six of serious partying just weren’t enough. The following morning 20 boats headed out for the single-handed race, including Old Bob. That boat had been a bit of an irritation to the committee, as they had to wait patiently for Bob to finish before they could pull the marks and join the fun on shore. After all entrants finished that day, except Old Bob, we saw his red sails hanging on the horizon and heard on the radio, “Committee boat, committee boat, this Old Bob. Should we leave Montserrat to port or starboard?” A very long pause was followed by, “I’d leave it to starboard, skipper.”

At two that afternoon, an eclectic collection of dinghies gathered at the Admiral’s Inn for the Gig Racing, coinciding with British tea and scones served by ladies in bouffant hats. I entered my old El Toro in the sculling race before I realized the unusual rules. They call it the Don Street Race, and each contestant must scull the course as Don would, holding an open Heineken. You can’t drink any beer before the start, but you must finish it before the end. Though I was the first woman to finish, my performance was definitely hampered by the beer and I wondered if the local brew, Wadadli, might have given me more speed.

Our other dinghy, a two-bow boat from Petite Martinique, was raced all day by Bruce, blinding people with her new lime-green paint and matching sail. Funny World must have bedazzled the committee, because they chose her over several gold-leafed beauties as winner of Concourse D’elegance … first place!


Funny World wins the Concourse D-elegance!

That night, captains and crew gathered in Nelson’s Dockyard for the awards ceremony. Regatta Chairman Kenny Coombs took the podium and the hooting and hollering began. He started by thanking the generous sponsors, Panerai Boat International, and a dozen others. Next he thanked the owners, skippers and crew for sailing a gentleman’s regatta that ran without a single protest. Captains, one by one, took the stage to claim prizes until the entire crew of Radha marched up for their second-place award. We could barely contain ourselves, until Kenny announced, “And in first place, the lovely Lone Fox!” Behind proud Ira, 17 of us gleefully followed him onto the stage, shaking any available hand on the way. And that was it … the end of an exhausting, exhilarating, unforgettable week, and I can hardly wait for the next one.


The Lone Fox crew stands at attention for the Parade of Classics.

Jan