Antigua Sailing Week is about to celebrate its 50th anniversary. Here's how to get the most out of this one-in-a-lifetime-regatta

Laura Ivill

Taped onto the stern of an elegant teak-decked sailing boat in Nelson’s Harbour, Antigua, was a handwritten note. “Volunteer crew wanted: here to Nantucket via the BVIs & Bermuda. Leaving early May. Looking for some sailing experience?”

It’s the kind of note that triggers wild visions of leaving your old life behind and cruising the sunshine-drenched waters of the West Indies all the way to Nantucket, south of Cape Cod, USA. Maybe one day.

Antigua is a mecca for yachties. Once a year, in December, the big money comes in for the Antigua Charter Yacht Show, and every spring it’s Sailing Week, a much more casual affair, fitting with the island’s low-key and surprisingly undeveloped nature. Roadsides are dotted with bungalows on stilts, their colourful paintwork peeling in the tropical heat, and a great many of the 365 beaches are untouched and empty.

Late April – an ideal time to visit this year-round climate – is Sailing Week, when enthusiasts congregate for all-comer races off the south coast and a circumnavigation of the island, all 108 square miles of it. This years marks the 50th anniversary of the event, so expect a bonanza year.

Us Brits feel right at home in the Mainbrace Pub, which feels as authentic as any ancient Thameside tavern, with hand-hewn beams and nautical antiques.

For race-watchers, you can get out on the water in the Chase the Race event at the start of the week. The best of the action, however, is always to join in as crew, signing up on one of the many yachts taking part, or perhaps chartering a whole boat, if, say, your sailing-club buddies fancy some fun in the sun. Although you’ll find one or two professionals at the helms, Antigua Sailing Week is all about the taking part, getting your adrenalin fix in the rolling seas of the Caribbean, kicking back and having a great holiday.

The daily races are between buoys off the south coast bays of Nelson’s Dockyard, English Harbour and Falmouth Harbour. If these sound wildly romantic, they are. Nelson’s British fleet in the Caribbean was berthed here due to the sheltered deep waters, and if your sail needs a running repair then it will likely be in one of the original 18th-century workshops. Nelson’s Dockyard is an authentic step back in time, so much so that it was awarded UNESCO status last summer. Don’t miss the ridiculously quaint museum, which has, so they say, Horatio Nelson’s very own telescope.

The waterfront is the hub for prize-giving, and the stage doubles for the evening entertainment, with giant speakers pumping out reggae, soca, DJ sets and headline acts. Freshly caught seafood is served at communal outdoor tables. It’s the place for casual socialising and swapping stories of the day’s high drama.

Nelson himself couldn’t wait to get the hell out of this “vile spot”, but anyone who secures one of the 14 suites in The Copper & Lumber Store Hotel, built in 1789 to store the materials needed for repairing the fleet, will have themselves a better time of it. Us Brits feel right at home in the Mainbrace Pub, which feels as authentic as any ancient Thameside tavern, with hand-hewn beams and nautical antiques.

Next to the Dockyard is the five-star Inn at English Harbour, which has contemporary Caribbean styling in its 28 suites and beach cabanas, with mahogany floors, four-posters and verandahs leading onto the beach or gardens. Or try The Admiral’s Inn with its infinity pool, hammocks, spa and private beach. And for the ultimate in escapist jet-set luxury, Jumby Bay, a Rosewood Resort, is set on its own island with private water taxi.

All-inclusive resorts in the south and southwest are popular with families, but can seem pricey. Suites at Carlisle Bay are spacious, simply furnished and set around a bay of golden sand with a backdrop of magnificent hills, typical of the island’s natural beauty.

A must-do walk along the coastal path takes you out of the resort up along the bluff to Rendezvous Bay, where you’ll be greeted by a majestic sweep of powdery sand. From here you can swim to your heart’s content, while yachts race madly between points out to sea.

It’s not easily accessible by car, and there’s no café, so you may well have the place all to yourself (that is, until the planned hotel arrives). You can enjoy this as a circular walk from Falmouth Harbour, too.

Antigua’s steady trade winds give these islands a decent blow, which is why it’s a popular destination for all-inclusive family sailing weeks whatever your level, beginners and race-fiends alike.

50th Antigua Sailing Week takes place between 29 April and 5 May. To find out more visit Virgin Atlantic flies three times a week from Gatwick to Antigua from £479, to book visit or call 0844 2092770. Doubles at Carlisle Bay cost from £621, including breakfast and afternoon tea. Visit For information on the island, visit visitantigua​

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