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Antigua Sailing Week attracts the world’s

top racing yachts, including the 57-foot

Charisma, owned and skippered by Spanish

banker Alejandro Pérez Calzada.

story by herb mccormick

for salty dogs and landlubbers alike, regattas in the caribbean are one part full-sail racing

extravaganza and one part nonstop party, and antigua sailing week may be the biggest bash of them all.

t h r e e s h e e t st o t h e

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With its crew of 28, owner Mike Slade’s 100-foot Leopard 3

handily won Sailing Week’s Guadeloupe-

to-Antigua sprint. Opposite: Sailors

and spectators party at Shirley Heights.

Before long, sailing week’sreputation as a carnival

of epic proportions was sealed.

There’s no oTher way To puT iT: MargareT gryzelko

looked hot. Trim and blonde, wearing a light summer sun-dress, she’d left her everyday life as a mom back in Miami a long way away, literally and figuratively.

it was a Tuesday in april on the island of antigua, atop the breezy peak known as shirley heights, at the midway point of the annual festival of offshore yachting and onshore mayhem called sailing week. The sunset party at shirley, like so much of the scene at sailing week, is a highly anticipated ritual, and the sun had just done its part by vanishing behind a faraway ridge. Down below, the harbor lights at Falmouth started to flicker. on high, the steel band was beginning to simmer. soon enough the dance floor began to sway and percolate.

and gryzelko and her pals, all dressed to the nines, were right in the thick of it.

The springtime regatta in antigua has been a fixture on the yacht-racing calendar for more than 40 years now. its roots are modest: looking to extend their bookings at least one more week, the local charter-boat skippers and hoteliers organized the late-april regatta as a wrap-up to the tourist season. The general idea was to race from one beach resort to another, anchor the boats, throw a huge bash and then do it all again

the next day. The inaugural edition of sailing week drew a handful of local boats, mostly charter craft, but word soon got out about champagne sailing through azure seas, propelled by steady easterly trade winds — as well as the raucous, non-stop parties — and antigua’s little regatta caught fire. Before long, sailing week was drawing the hottest boats and the best sailors from near and far, and its reputation as a carnival of epic proportions, both on the water and off, was sealed.

Today, antigua sailing week continues to go strong. Though the fleet is somewhat diminished from the regatta’s record-setting years, the 2009 running attracted an impres-sive field of 140 boats, including such grand vessels as British yachtsman peter harrison’s stunning 115-foot ketch, Sojana. The trades still honk, and the racing remains spectacular.

as for the parties, they’ve mellowed somewhat, but they’re cranking along too. The midweek break from racing, a dawn-to-dusk bacchanal once known as lay Day, has gone by the wayside, and with it the infamous wet T-shirt contest and re-lated shenanigans. it was fun while it lasted, but frankly the time had come. The Fort James Beach Bash, the shirley heights sunset party, Jolly harbor Day, and the prize-giving ceremony in the rich, historic confines of nelson’s Dockyard, among many less-formal occasions, carry the celebration forward.

These days, the case can be made that going to sea is hardly a requisite to enjoy sailing week. Much of the racing is still conducted over point-to-point courses around the picturesque island and its myriad beaches. Thus, with a rented car, a suit-able map, a copy of the sailing instructions and a sense of adventure, one could spend a most pleasurable holiday fol-lowing the colorful action via coastal roads, stopping now and again for a swim and a rum punch — not for the driver, of course — and then catching up with the sailors for the post-race parties.

Two years ago, Bostonian Becky wheatland set off for the event with a very similar plan. “My friend and i were sick and tired of the cold and decided to just head for antigua,” she says. “we stayed at a hotel, watched all the races, went to the parties and had a great time.” But wheatland, an ac-complished small-boat sailor, also wanted to participate, and by week’s end she secured a slot on a boat for a couple of days of racing.

This year, smitten with her first experience in antigua, she decided to raise her game. The British-based company ondeck ocean racing (ondeckoceanracing.com) offers berths aboard Caribbean race boats on a person-by-person basis, for all levels of experience, and when the gun fired to start the first race of sailing week, wheatland found herself trimming the mainsail on a 65-foot offshore sloop. it was her first time competing aboard such a powerful, purposeful yacht.

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“i learned so much,” she says. “i’d absolutely recommend it to anyone who wants to have a good week of racing, get a ton of sailing experience and party in antigua.”

Margaret gryzelko and her friends would second that opin-ion. They’ve been returning to sailing week for several years now, and they have their routine down pat. Many participants from the united states and abroad charter bareboat yachts from companies such as sunsail (sunsail.com), recruit some pals as crew and to share both the costs and the fun, and then compete in the bareboat divisions, living aboard the boats during the the regatta. But gryzelko’s strategy is a tad more upscale.

along with her regular group of mates — a mixture of guys and gals, some experienced sailors, others beginners — she charters a crewed yacht each year with a hired captain, who in turn gathers a few of his sailing buddies (it’s not too tough to round up sailors eager to race with gryzelko’s mob) from island water world (islandwaterworld.com) in st. Martin. last year, she and her friends raced hard each day, repaired to a sumptu-ous rented villa for showers and refreshments afterward, and then hit their favorite parties each evening.

“we never stay on the boat,” she says. “some nights we eat at home, and others we dine out. our house was lovely.”

For those thinking of launching their own visit to sailing week, gryzelko has some hard-earned advice. “go to the gym a lot and catch up on your sleep,” she says. “otherwise you will not survive. But by all means come and see it. i’ve been to other race weeks, but only antigua is antigua.” » The 43rd Antigua Sailing Week is set for April 24-30, 2010. For more information, including a list of suggested accommodations, visit sailingweek.com.  Sa il o n »

Antigua’s English Harbour spreads out below Sailing Week’s party epicenter, Shirley Heights. Opposite: Onshore and on deck, steel-pan music fills the air.

these days, the case can Be made that going to sea is hardly a

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S t. M a a r t e n » S t. M a a r t e n H e i n e k e n

regat ta » M a r cH 4 –7, 2010 » early each March, the wind-swept isle of st. Martin plays host to what’s become the largest sailing event in the Caribbean, rou-tinely attracting upwards of 300 boats. The motto for the st. Maarten heineken regatta is “serious fun,” and there’s no question that the diligent pursuit of pleasure becomes an earnest quest for competitors, islanders and spectators alike. yes, the trade-wind sailing is fan-tastic, but so too are the après-racing parties, some of which are staged on the Dutch-side beaches, others in the French-side port town of Marigot, and all of which are fueled by an endless supply of icy green bottles, courtesy of the regatta’s longtime title sponsor. when the racing is said and done, top-flight musical acts like the neville Brothers, the wailers, the Marley Brothers and shaggy headline a big bash on kim sha Beach. it’s worth not-ing that 2010 marks the st. Maarten heineken regatta’s 30th anniversary, so needless to say, the fun will be especially seri-ous. heinekenregatta.com » S taY: st. Martin has no shortage of great places to stay, but a good choice during the regatta is the sonesta Maho Beach resort & Casino. not only can you watch some of the racing right from the resort’s beach, but it’s also a short hop away from the event headquarters at the st. Maarten yacht Club. and the Club’s porch is a choice spot to sink a sundowner as the race boats return to simpson Bay’s inner lagoon via the adjacent drawbridge. Be sure to book a pool- or ocean-view room. From $219 in low season ($290 high); 800-766-3782; sonesta.com/mahobeach

S t. D av i D ’ S , g r e n a D a » g r e n a D a c l a S S i c Ya c H t r e g at ta » M a r cH 4 –7, 2010 » The scenic “spice island” of grenada hosts one of the more elegant yachting events in the Caribbean. staged off the isle’s rugged southeastern flank, the four-day grenada Classic yacht regatta is competitive sailing on a grand, traditional scale, and the classic ketches, schooners, yawls, sloops and tall ships that participate are all meticu-lously maintained and masterfully piloted. grenada’s event — moved from February to March for 2010 — is one in a

burgeoning circuit of classic regattas in the Caribbean and abroad, attracting a passionate and eclectic group of wooden-boat aficionados. There are many superb onshore vantage points from which to watch the competition, and the parties following are noted for their grenadian hospitality and variety of live music. grenadagrenadines.com » StaY: in addi-tion to being one of grenada’s loveliest small resorts, with 11 colorful villas and cottages set on 18 acres, Bel air plan-tation, along st. David’s harbor, serves as regatta headquarters. From $150 in low season ($250 high); 866-504-3359; belairplantation.com

tor tol a & virgin g orDa , Bvi » Bvi Spring

regat ta & Sa il in g Fe S t iva l » M a r cH 29

– a pril 4 , 2010 » since the days of admiral nelson, the bus-tling blue waters of sir Francis Drake Channel and the rich cruising grounds of the British Virgin islands have tweaked many a sailors’ heartstrings like few other places. The islands remain a nautical paradise, especially each april during the BVi spring regatta & sailing Festival.

Based out of nanny Cay resort, on the island of Tortola, the regatta is really two events in one. The four-day sailing Festival kicks it off, with crews racing up the channel to Virgin gorda and a warm welcome at the Bitter end yacht Club, where a full schedule of dinghy racing, awards cer-emonies, jump-ups, windsurfing, cookouts — or just relaxing snorkels or dips in the pool — awaits. Bring the family or your nonsailing mates; this is a regatta everyone can enjoy.

after a couple of days at the Bitter end, the event resumes with a race back to nanny Cay, and that’s when the real com-petition begins. The three-day BVi spring regatta is about old-school yachtsmanship, with numerous short races each day and excellent parties at the regatta Village — replete with food and libations — each night. bvispringregatta.org » StaY: To get the full experience, plan to spend the first half of your week at the Bitter end yacht Club, on Virgin gorda. From $530 in low season ($760 high); 800-872-2392; beyc.com. Then spend the second half at the nanny Cay resort, on Tortola. From $105 in low season ($150 high); 284-494-4895; nannycay.com

traditional keelless sailboats compete in the Bahamas.Above: Hobie Cats get in on the racing at the Bitter End yacht Club in the BVi.Opposite: Boats vie for Best-Dressed Crew and Most Photogenic prizes at Grenada’s Classic yacht Regatta.

anTigua’s sailing week may be the best-known Caribbean regatta, but there are plenty of other noteworthy annual sailing events from the exumas to the grenadines. whatever the competitive focus — classic yachts, indigenous workboats or flat-out grand prix racers — each of the following regattas steps smartly in tune with the singular aura of its respective venue. whether you’re looking to hoist a sail yourself or prefer to hit the parties and soak in the ambience, a visit to these islands during regatta time will add a salty taste to your travels.

fun for the whole crew

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Beq uia , t He g ren a D ine S » Beq uia e a S t er regat ta » a pril 1–5 ,

2010 » The fastest-growing event in the southern Caribbean, the Bequia easter regatta is an ideal excuse for a springtime dash to the islands. The regatta itself is an alluring mix of old and new, with a racing fleet that’s roughly half contemporary racers and half traditional double-enders from Bequia and the nearby islands of Canouan and Carriacou. along with the racing boats, a sizable spectator fleet of a hundred yachts or more drops anchor in admiralty Bay to enjoy the party. The easter holiday adds a festive note to the proceedings for locals and visitors alike; in concert with the requisite music and dancing, the popular sand Castle/sand sculpture Compe-tition and Crazy Craft race on easter sunday round out the fun. Book early: The easter regatta draws prodigious crowds. begos.com/easterregatta » S taY: at the centrally located Bequia Beachfront Villa hotel, check out the racing and par-take of the festivities from your own one- to four-bedroom cottage by the sea. From $207 in low season ($311 high); 800-367-8455; bequiabeachfrontvillas.com

great exuMa, tHe BaHaMaS » national FaMilY iSlanD regatta » april 20 –2 4 , 2010 » look across elizabeth harbour’s expanse of turquoise water on an afternoon during the third week of april and you might feel like you’ve drifted astern a good half-century. The glorious view from the Bahamian port of george Town, great exuma, hasn’t changed too much since then, for it was 1954 that the island hosted the first running of what would become the national Family island regatta. The sponge and crayfish seasons were over, and a sailboat race seemed like a good excuse to spruce up the workboats — and perhaps lodge a wager — before putting the boats to rest. no one suspected that this grass-roots racing would become a na-tional obsession and that an entire festival of parties, parades, fashion shows, music, food, drink and camaraderie would be spawned from these good-natured seagoing skirmishes. But that’s exactly what has happened.

These days, the national Family island regatta, open ex-clusively to boats built and designed in the Bahamas, is a revered institution, one largely responsible for maintaining the craft of traditional boat building. with a huge sail plan, as well as long planks on which the crews hike out when cleav-ing upwind, this type of vessel is a handful. Capsized boats are frequent, soaked sailors a given. nationalfamilyislandregatta .com » S taY: Just a stone’s throw from the event epicenter at regatta park, georgetown’s Club peace & plenty will put you squarely in the action. From $155 in low season ($180 high); 800-525-2210; peaceandplenty.com

r oa D BaY, a n g uil l a » a n g uil l a regat ta » M aY 7– 9, 2010 » The northernmost of the leeward islands, anguilla has a rich and storied history of competitive sailing. The sheltered harbor of road Bay serves as the perfect racecourse, and the neigh-boring beach at sandy ground provides ample room for the parties. all you need are sailboats, and the anguilla regatta, run over a three-day weekend in early May, attracts scores of them. The partying starts on Thursday evening, and the racing gets under way on Friday morning. on sunday, the festivities

culminate with visiting crews joining locals to race on island workboats, a tradition unique to this charming grass-roots regatta. you can watch much of the competition from the shore and then retire to sandy ground and its wide array of restaurants, or enjoy fresh local fare or a barbecue supper right on the beach. anguillaregatta.com » S taY: Quaint, well-equipped and affordable, sea View apartments is just a short stroll away from the regatta bustle at sandy ground. From $60 year-round; 264-497-2427; inns.ai/seaview

J o S t va n DY k e , Bv i » F ox Y ’S Wo o D e n B oat regat ta » M aY 28 –

30, 2010 » Foxy’s, tucked under the palm trees at the head of great harbor on Jost Van Dyke, may just be the quintessential Caribbean beach bar, where music, food and laid-back vibes go hand in hand. and Foxy’s wooden Boat regatta, which just celebrated its 35th anniversary, might well be the coolest gath-ering of well-traveled wooden boats. like the man who runs the place, Foxy Callwood, both the regatta and the watering hole are one of a kind. The sailing and the parties are on equal terms here, as the entire point of the exercise is to celebrate good old boats and the people who love them. Foxy’s wooden Boat regatta takes place over Memorial Day weekend. foxysbar.com/woodenregatta.html » StaY: The very best way to enjoy Foxy’s — and the rest of Jost Van Dyke — is on the beach, under the stars. Catch a ferry, pitch a tent, lose your shoes, and either find yourself a berth on a boat or hike and swim the days away until the racers are anchored and back at the bar. Call proprietor ivan Chinnery at the white Bay Campground to reserve your campsite. Campsites $20 year-round; cabins from $45 in low season ($65 high); 284-495-9358; ivanscampground.com ✸

Bequia’s Easter Regatta is gaining momentum among racers of vintage and modern boats.Above: On tortola, Nanny Cay Resort hosts the BVi Spring Regatta. Opposite: Pouring the celebratory bubbly in Anguilla.

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