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A Trade Wind Classic

The caliber of yachts in the Antigua Classic Yacht Regatta leaves even old salts wide-eyed with wonder

The caliber of yachts in the Antigua Classic Yacht Regatta leaves even old salts wide-eyed with wonder

For those who have not been lucky enough to compete in the Antigua Classic Yacht Regatta, or been on hand to witness this extraordinary festival of sail, allow me to paint for you something of a picture.

First of all, our island is a small one — about 108 square miles — and every yacht that arrives for this regatta has probably sailed many ocean miles to get here. Antigua is in the middle of the trade wind area, and there is really nothing to stop the wind and sea over 3,000 miles of the Atlantic. Normally the weather is warm and sunny, with enough wind to build more waves than most visitors expect. On the whole, the sea is flecked with white as the tops of the sizable rollers tumble into the troughs.

Each April classic yachts from all over the world arrive in Antigua to compete in a series of races that leave both participants and spectators smiling. Organized by the Antigua Yacht Club, the event this year takes place from April 14 to 19, between the Mega Yacht Challenge for boats in excess of 100 feet and the granddaddy of all Caribbean sailing events, Antigua Sailing Week.

The classic regatta began in 1987 and today attracts more than 50 yachts and hundreds of sailors, both amateur and professional, the majority from the United States and Europe. It has been run for years by Kenny and Jane Coombs, with a group of enthusiastic volunteers.

The racing takes place off the island’s south coast, where the water is deep as soon as you leave the shoreline. The courses consist mainly of close and broad reaches, but there is just enough beating and running to allow most of the varied types of vessels to strut their stuff. Spectators can watch most of the racing from atop the many hills on the south coast. Compared to the gray and unfriendly sea waters around Europe and the United States, our normal clear, blue ocean — combined with a pleasant temperature — is as close to perfect as any sailor could wish for.

From just outside FalmouthHarbour a variety of rigs and hulls jostle and plunge through the lively sea. From the smallest of about 26 feet to the largest, often a tall ship well in excess of 300 feet, the regatta fleet presents a sight that leaves old salts like me completely wide-eyed. Elderly gentlemen, with beards and cloth caps, grimly hang on to tillers and wheels, while nattily attired crews on the bigger boats line up along the windward rails in true America’s Cup fashion.

This event is unlike other island regattas, where female sailors sometimes race wearing skimpy swimsuits. It is a race where owners, skippers and crews truly admire the other yachts around them. It is a race where protests aren’t encouraged, and neither enthusiasm nor expertise is lacking.

The final day of the regatta is taken up with gig racing for both oarsmanship and sailing. Spectators watch from the lawn of the historic Admirals Inn at Nelson’s Dockyard, where the sort of cream tea that one normally finds on the upper reaches of London’s ThamesRiver is savored. There also is a classic yacht parade held immediately after the final race, through Nelson’s old naval base in EnglishHarbour.

It is generally agreed that all who are true aficionados of classic yacht design owe a huge debt of gratitude to Elizabeth Meyer. She rescued the hulk of Charles Nicholson’s beautiful J Class yacht Endeavour, and rebuilt and restored her to better-than-new condition — but stuck to the original design. In doing so, Meyer, who founded the InternationalYachtRestorationSchool in Newport, R.I., set the parameters for the many who followed her.

And while genuine classics from yachting’s gilded age are unmistakable at the regatta, you might wonder about the “modern classics,” those with the fine lines of a traditional yacht but built and rigged using modern materials and techniques. To be eligible to participate, according to the Antigua Yacht Club, “All yachts, traditional boats and ships should be of the ‘one off’ type, with a hand-crafted hull. All entries should have a full keel with a keel hung rudder; however, short keels with a separate rudder may be accepted if the yacht is of a traditional design. All entries should be fine examples of tradition, craftsmanship in hull and rig, and be in good condition. Recently built yachts, using modern materials, built in classic style and grace to exceptional standards, may be accepted into the ‘Spirit of Tradition Class.’ ”

Other classes include Traditional (fishing or cargo vessels built or converted to sail); Vintage (yachts with a full keel designed and launched before January 1950); Classic (yachts with a full keel designed and launched after January 1950); and tall ships (sail training and passenger vessels). Classes are subdivided according to performance, size, type and rig.

As in most regattas of this type there is some contention, for each year it seems someone has a bit of a gripe about entries in the Spirit of Tradition Class. Decisions made by the Antigua Yacht Club’s regatta committee to include specific modern classic designs have been adhered to by classic regatta organizers around the world. New boats are allowed to race as long as these “new classics” follow the rules. If this allowance hadn’t been made it’s quite possible that present-day classic regattas would have faded to history due to a lack of classic yachts. Certainly this would have been the case with the big boats.

Now, however, the people who truly appreciate the look of a genuine classic yacht can find them at events around the world. Some may be built of modern, longer-lasting materials and may even have a fairly modern — to a point — underbody. This means that at classic yacht regattas like the one to be staged off Antigua showcase genuine old craft competing with other boats of their age and type. New classics, as long as they comply with the rules, race against each other.

And you know at these events, even the traditionalists sometimes get the surprise of their lives.

For more on what constitutes a classic, visit

Island resident Jolyon Byerley was instrumental in the early days of the Antigua Classic Yacht Regatta and Antigua Sailing Week. A former commodore of the Antigua Yacht Club, he has decades of sailing under his belt and has been overall winner of Sailing Week three times. Byerley now runs Lord Jim’s Locker and Boutique at the Antigua Yacht Club Marina with his longtime partner Judy McConnachie.


The little yacht that could

By Patrick Reilly

This is the story of a small but able boat named Grace that I sailed south one winter to the islands. It is also a story about the Antigua Classic Yacht Regatta, in which my little 23-footer proudly competed last spring.

The Antigua Classic is my kind of sailboat race. The first year I participated was 2002 aboard the 90-foot gaff-rigged ketch Vileehi, skippered by race organizer Kenny Coombs.

“If you’re worried about losing,” Coombs said, “you’re missing the point.” That pretty much sums up the spirit of the regatta. Although the competition can be fierce in some classes, the main point is to gather a bunch of beautiful classic yachts and get them sailing together.

After that first regatta I ended up sailing to France aboard Vileehi. I worked for another month aboard her, then did a bit of backpacking in Eastern Europe before heading home to Maine late that summer. I was looking for a boat, and Grace exceeded my expectations.

The search

I grew up on the coast of Maine, cruising aboard my family’s small sailboat. I loved reading sea stories by adventurers like Thor Hyerdahl, Bernard Moitessier and Joshua Slocum. The idea of pitting one’s skills and self-reliance against the elements struck a chord with me.

Coupled with serious wanderlust, I figured a career as a yacht captain was a natural choice. But after a while I grew disillusioned with working on other people’s yachts. I wanted the freedom to sail how and where I chose, and I yearned for an adventure like those I had read of in my youth.

I had been searching for a cruising boat of my own, and after combing the Caribbean and Europe I finally found Grace in October 2002 … back in Maine. She is a 23-foot strip-planked, gaff-rigged Maxwell cutter — super simple, with no engine and minimal electronics. I wouldn’t have minded a few more feet in length or inches in headroom, but she was all I could afford, and she was structurally sound and well built.

Grace was designed by naval architect Mike Kaufman of Severna Park, Md., and home-built in 1985 by a professional in Port Townsend, Wash. Patterned after an English working boat, she’s a cross between a Falmouth cutter and a Bristol Channel cutter. These boats were renowned for their seakeeping abilities, and I hoped Grace would live up to her reputation.

My original plan had been to get right at outfitting Grace, then sail straight to the Caribbean from Maine. However, by the time she was ready for sea the harbor was freezing over, and leaving Maine in December on a 23-foot engineless sailboat would be close to suicide. I decided to truck Grace to Beaufort, N.C., and leave from there. I would have preferred to leave even farther south, but Beaufort was as far as I could afford to pay the truck driver. At least it put me below CapeHatteras.

Leaving Beaufort was a surreal experience. It was a beautiful January day with light northwesterly winds, and some friends I had met during my stay accompanied me out of the harbor in their little Sharpie schooner. As I left the harbor, warships and landing craft ferrying marines surrounded me — part of the buildup to the March 2003 invasion of Iraq. The air was filled with the sound of the ships’ engines and sonic booms from jets streaking the sky with contrails. I was stepping into the unknown at a time when it seemed like the world was tearing itself apart.

All the activity added to my anxiety about my upcoming voyage. I had done all that I knew how to prepare Grace, and I had confidence in her and my own abilities. But because of the time of year, I was counting on running into heavy weather. For all my preparation, I wouldn’t know for sure if Grace could handle it until I was out there.

Washing machine

My primary goal was to cross the Gulf Stream as soon as possible. I made good time the first day out as the wind gradually picked up. It wasn’t until I was almost out of the Stream that things took a turn for the worse. The wind was still out of the northwest but had picked up to 25 to 30 knots. The sea had gotten steeper and more confused, and the forecast called for deteriorating conditions. I drove Grace as hard as I could under double reefed main and staysail.

Down below was like being in a washing machine, with water crashing over the deck and finding its way into the cabin. The most serious leak was around the main hatch, where a wave would smash into the drop boards and send water shooting through the gaps. In short order everything that wasn’t in a dry bag was soaked. Needless to say, it was the dead of night when this was all happening.

By morning the wind had picked up to 30 to 35 knots, but I had made it out of the Gulf Stream. The seas became more regular, and I was able to start putting the cabin back in order.

The rest of the trip was a series of one gale after another. The worst blew 45 to 50 knots sustained, with higher gusts. Nothing as bad as that first night, though. I’d heave-to, and Grace would ride the storms like a duck. In fact, I had a harder time between gales. The wind would drop and change directions, leaving a confused sea, and Grace would spend hours being tossed on her beam-ends. These were times that really tried my patience.

After 17 days at sea I finally made landfall on Tortola, the largest of the British Virgin Islands.

On to Antigua

Time has a wonderful way of giving a person selective amnesia. My voyage to the islands had been hard, but the fight had made the good points stand out all the more. I never felt more alive than when I was out on the ocean. I started to contemplate another voyage, this time across the Atlantic.

I had spent a year or so bouncing around the Caribbean, sailing and working, and winter of 2004 found me back in the Virgin Islands on St. John to refit a yacht that had run aground. I was ready to cross the pond, but I first wanted to sail to Antigua for one more Classic Yacht Regatta — this one aboard my own boat.

As crew I was lucky to have along two of my best friends from home. Karl and Kristen Brunner run Downeast Friendship Sloop Charters out of Southwest Harbor, Maine. Both are very experienced sailors, and I knew they would be good company. I picked them up in Virgin Gorda, where they had left their cruising boat in a yard to return to Maine for the summer season.

Our sail to Antigua was only about 200 miles, but it took us four days. (Remember, no engine. And the passage involves beating into the trade winds and current.) At 23 feet Grace is a bit tight for three people. It was a testament to our friendship that we didn’t get on each other’s nerves. In fact, we had a ton of fun.

Our second day out we made negative five miles as we drifted in a calm. No worries, we spent the day listening to music, sipping mimosas and swimming. We did start to have second thoughts about swimming, though, after seeing a shark make a run at the oar Karl was rowing with. Later that day we were rewarded for our patience in the calm with a beautiful sunset, a good breeze and a fresh-caught tuna. Our spirits weren’t even dampened after spending an entire night beating against the current between St. Eustatius and St. Kitts. We decided to rename the long, narrow point on St. Kitts we were trying to round “Point You’re Screwed.”

The reward

Antigua during the Classic Yacht Regatta is a sailor’s reunion of sorts, and we spent our first day catching up with old friends. The regatta takes place at the end of the Caribbean sailing season, so it’s a good place to meet up before everybody heads their separate ways. It attracts an eclectic crowd, from the megayacht jet set to cruising families on shoestring budgets. The one thing everyone has in common is a love of classic boats.

The first morning of the regatta I woke to the sound of engines warming and people calling to one another across the docks. Karl and Kristen had moved ashore and were to meet me for an early start. Our “pre-race preparations” had carried on late into the night, so I wasn’t surprised when no one showed up on time. I got a little concerned when my neighbors started slipping their dock lines. I spotted my crew coming down the dock, and they quickly loaded their gear. We were off to the starting line.

Our first start was complete mayhem. As we reached the line, Karl was still coiling down halyards and securing loose gear. I was at the helm doing my best to avoid other yachts, which seemed to be coming from every direction. Kristen stood in the companionway and listened to the VHF as she tried to determine the starting sequence. We were in the Classic Class D group, designated by a green flag. I found my friend Ashley Butler, whose 32-foot Thames bawley Sally B was in our class, and followed him. Before I knew it we were surrounded by green flags headed for the line. By pure luck we managed to make a decent start, and we were on our way.

Once under way I could take the time to appreciate our surroundings. Century-old gaffers mixed with classic racing yachts in Bristol condition. The trade winds were blowing around 15 knots, and everyone was driving hard under full sail. By the time we were halfway to the first reaching mark the big yachts started to catch up with us. Soon J Class and Spirit of Tradition Class yachts were blowing by us as if we were standing still. Many of these yachts took the extra time to dip below us, but when one did sail to windward it was like sailing behind a wall. The wind would drop to nothing, and Grace would flog around in the waves until it passed. No harm done, though, and it was well worth having a ringside seat to these powerful displays of sail.

By the end of the race the wind had died to less then 10 knots, and we had a photo finish with Sally B, short-tacking like racing dinghies. The light winds favored Grace, and after picking up a huge lift off Pigeon Point we were able to sneak ahead. To top the day off photographer Michael Kahn gave us a copy of his book for his “Most Photogenic Yacht of the Day” award.

The next day’s race was a butterfly-shaped course aptly named The Butterfly. This was the longest of the three races and with the most legs to windward — fine for the big boats but a bit of work for us little guys. Though we managed to get under way on time, we ended up having another fire drill for a start. Using my “follow the herd” technique, we were able to get off OK.

The wind had picked up from the previous day, and we were soaked with spray in no time. The seas also had kicked up, and it was tough beating into them. By the end of the race most of the bigger boats had lapped us. This made for some interesting mark roundings. We would be struggling to make a windward mark as boats three to five times our size were converging on us at full speed. I was worried about their skippers even seeing us, and I sure wasn’t going to be calling “starboard” on any of them. We made it in that day sunburned, dripping wet and tired, but grinning fromear to ear after a great day of sailing.

The final day of the regatta was a beam-reaching drag race called “The Cannon.” There’s not much strategy involved. It’s more about letting crews get a good look at all the competitors as they sail the back-and-forth course. We actually made it to the line early, but as it turned out we had our worst start yet. Things had gone much better when we planned less and left things more to luck.

Winds had picked up to 20 to 25 knots, and the seas had been building overnight. We had way too much sail up, but I pressed on anyway. Let’s just say I got caught up in the moment, though I really should have taken down the main topsail. To make matters worse, the constant back and forth of the boats churned up the seas so that they came from everywhere. It was all we could do just to hold on as Grace ripped along, sometimes over and sometimes under the waves.

After the race, when we mentioned which boat we were on, everyone recognized us as “the little boat that sailed on her ear.” The previous day’s soaking was nothing compared to the last day’s. I was glad to make it back in with the boat in one piece and all hands accounted for.

The next night there was an awards ceremony and party at Nelson’s Dockyard. We weren’t surprised when we received the award for being the smallest yacht in the regatta, but as it turned out we had won our class, as well as being awarded “Best Performance for a Yacht under 40 feet.” But winning or losing isn’t why so many people had come to Antigua for the regatta. It was all about good sailing, appreciating classic boats, meeting old friends and making new ones.

As the festivities came to an end, boats started filtering out of the harbor. The majority were bound for New England or Europe, with some off to more exotic destinations.

Karl and Kristen did a yacht delivery back to Maine and a summer of Friendship sloop chartering. I sailed to St. Martin, where I spent a few weeks preparing for my next solo voyage, this time across the Atlantic. I left at the end of May and sailed to Ireland via the Azores, but that’s a story for another time. Grace is in a boatyard on ValentiaIsland off southwest Ireland, ready for my next adventure; I plan to fly to Ireland and spend the summer sailing her around Iceland.

I’m hoping to find a sponsor to help offset the cost of readying her for that adventure, since I shredded my mainsail on the voyage to Ireland. I can be reached by e-mail at red