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 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.

St. Maarten
St. Maarten Heineken Regatta
March 4 - 7, 2010; heinekenregatta.com

Early each March, the wind-swept isle of St. Martin plays host to what's become the largest sailing event in the Caribbean, routinely 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 fantastic, 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 noting that 2010 marks the St. Maarten Heineken Regatta's 30th anniversary, so needless to say, the fun will be especially serious.  

STAY: 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

St. David's, Grenada
Grenada Classic Yacht Regatta
March 4 - 7, 2010; grenadagrenadines.com

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 meticulously 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.  

STAY: In addition to being one of Grenada's loveliest small resorts, with 11 colorful villas and cottages set on 18 acres, Bel Air Plantation, along St. David's Harbor, serves as regatta headquarters. From $150 in low season ($250 high); 866-504-3359; belairplantation.com

Tortola and Virgin Gorda, BVI
BVI Spring Regatta & Sailing Festival
March 29 - April 4, 2010; bvispringregatta.org

Since the days of Admiral Nelson, the bustling 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 ceremonies, 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 competition 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.  

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

Bequia, the Grenadines
Bequia Easter Regatta
April 1- 5, 2010; begos.com/easterregatta

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 Competition and Crazy Craft Race on Easter Sunday round out the fun. Book early: The Easter Regatta draws prodigious crowds.  

STAY: At the centrally located Bequia Beachfront Villa Hotel, check out the racing and partake 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. 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 national 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 exclusively 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 cleaving upwind, this type of vessel is a handful. Capsized boats are frequent, soaked sailors a given.  

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, Anguilla
Anguilla Regatta
May 7 - 9, 2010; anguillaregatta.com

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 neighboring 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.

STAY: 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

Jost Van Dyke, BVI
Foxy's Wooden Boat Regatt
May 28 - 30, 2010; foxysbar.com/woodenregatta.html

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 gathering 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.  

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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