three sheets

to the

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.
story by h er b mccor m ic k

Antigua Sailing Week

attracts the world’s
top racing yachts,
including the 57-foot
Charisma, owned and
skippered by Spanish
banker Alejandro
Pérez Calzada.

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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
Before long, sailing week’s
reputation as a carnival
of epic proportions was sealed.
5 6   c a r i b b e a n t r av e l+l i f e   
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 Rhoderick Grimes-Graeme; Right and previous spread: Cory Silken
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.
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.
c a r i b b e a n t r av e l m a g . c o m 57
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.

“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
BANANA PANCAKE/Alamy; Right: Holger Leue/getty images

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,

these days, the case can be made 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.

that going to sea is hardly a 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

requisite to enjoy Sailing week. set for April 24-30, 2010. For more information, including a list
of suggested accommodations, visit sailingweek.com. Sail on »

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fun for the whole crew
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.

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 burgeoning circuit of classic regattas in

regat ta » March 4–7, 2010 » Early each the Caribbean and abroad, attracting a
March, the wind-swept isle of St. Martin passionate and eclectic group of wooden-
plays host to what’s become the largest boat aficionados. There are many superb
sailing event in the Caribbean, rou- onshore vantage points from which to
tinely attracting upwards of 300 boats. watch the competition, and the parties
The motto for the St. Maarten Heineken following are noted for their Grenadian
Regatta is “serious fun,” and there’s no hospitality and variety of live music.
question that the diligent pursuit of grenadagrenadines.com » STAY: In addi-
pleasure becomes an earnest quest for tion to being one of Grenada’s loveliest
competitors, islanders and spectators small resorts, with 11 colorful villas and
alike. Yes, the trade-wind sailing is fan- cottages set on 18 acres, Bel Air Plan-
tastic, but so too are the après-racing tation, along St. David’s Harbor, serves
parties, some of which are staged on as regatta headquarters. From $150 in
the Dutch-side beaches, others in the low season ($250 high); 866-504-3359;
French-side port town of Marigot, and belairplantation.com
all of which are fueled by an endless
supply of icy green bottles, courtesy Tortol a & Virgin Gorda, BVI » BVI Spring
of the regatta’s longtime title sponsor. Regat ta & Sailing Festival » March 29
When the racing is said and done, top-flight musical acts like – April 4, 2010 » Since the days of Admiral Nelson, the bus-
the Neville Brothers, the Wailers, the Marley Brothers and tling blue waters of Sir Francis Drake Channel and the rich
Shaggy headline a big bash on Kim Sha Beach. It’s worth not- cruising grounds of the British Virgin Islands have tweaked
ing that 2010 marks the St. Maarten Heineken Regatta’s 30th many a sailors’ heartstrings like few other places. The islands
anniversary, so needless to say, the fun will be especially seri- remain a nautical paradise, especially each April during the
ous. heinekenregatta.com » STAY: St. Martin has no shortage BVI Spring Regatta & Sailing Festival.
of great places to stay, but a good choice during the regatta is Based out of Nanny Cay Resort, on the island of Tortola,
the Sonesta Maho Beach Resort & Casino. Not only can you the regatta is really two events in one. The four-day Sailing
watch some of the racing right from the resort’s beach, but it’s Festival kicks it off, with crews racing up the channel to

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 ss i c Ya c h t R e g at ta
» March 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
clockwise from left: Cory Silken; Tim Calver; George H.H. Huey/Corbis
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 Traditional keelless
sailboats compete
and excellent parties at the Regatta Village — replete with food in the Bahamas.
and libations — each night. bvispringregatta.org » STAY: To get Above: Hobie Cats
get in on the racing
the full experience, plan to spend the first half of your week at at the Bitter End
Yacht Club in the BVI.
the Bitter End Yacht Club, on Virgin Gorda. From $530 in low Opposite: Boats vie
for Best-Dressed
season ($760 high); 800-872-2392; beyc.com. Then spend the Crew and Most
second half at the Nanny Cay Resort, on Tortola. From $105 in Photogenic prizes
at Grenada’s Classic
low season ($150 high); 284-494-4895; nannycay.com Yacht Regatta.

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 Bequia, the Grenadines » Bequia Ea ster Regat ta » April 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 –24, 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. culminate with visiting crews joining locals to race on island
Bequia’s Easter The sponge and crayfish seasons were over, and a sailboat race workboats, a tradition unique to this charming grass-roots
Regatta is gaining
momentum among seemed like a good excuse to spruce up the workboats — and regatta. You can watch much of the competition from the
racers of vintage
and modern boats. perhaps lodge a wager — before putting the boats to rest. No shore and then retire to Sandy Ground and its wide array of
Above: On Tortola, one suspected that this grass-roots racing would become a na- restaurants, or enjoy fresh local fare or a barbecue supper
Nanny Cay Resort
hosts the BVI tional obsession and that an entire festival of parties, parades, right on the beach. anguillaregatta.com » STAY: Quaint, well-
Spring Regatta.
Opposite: Pouring fashion shows, music, food, drink and camaraderie would be equipped and affordable, Sea View Apartments is just a short
the celebratory spawned from these good-natured seagoing skirmishes. But stroll away from the regatta bustle at Sandy Ground. From
bubbly in Anguilla.
that’s exactly what has happened. $60 year-round; 264-497-2427; inns.ai/seaview
These days, the National Family Island Regatta, open ex-

Clockwise from right: Gary Bogdon; Wilfred Dederer Bequia; Macduff Everton/Corbis
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 » STAY: 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
Road Bay, Anguill a » Anguill a Regat ta » May 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
Jost Van Dyke , BVI » Fox y ’s Wooden Boat Regat ta » May 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 ✸

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