Antigua Sailing Holiday

On your first day, you’ll arrive in Antigua, and get a 40-minute transfer to English Harbour. The heart of Antiguan yachting for centuries, it’s a great place to start your sailing holiday. Nelson’s Dockyard, built by the British in the 18th century, sits in the middle of this well-sheltered natural harbour and is a real jewel in the region’s crown. Spend your first afternoon exploring the Nelson’s Dockyard UNESCO World Heritage Site, and the associated bakery, one of the Caribbean’s finest.

Sail out between two fortresses to start your holiday with a voyage east to the uninhabited Green Island, which is a favourite secluded, secret spot of ours (so maybe we shouldn’t be telling you...). The island is encircled by reefs, so caution is needed on approach. There is one very special bay that has a single mooring buoy. You’ll need a spotter on the bow to get through the reef, but once there it’s a wonderfully peaceful place to spend an evening, with amazing snorkelling, too. Take the dinghy ashore and stroll 100m across the island to the wild Atlantic coast.

Let your sails out and make steady progress along the coast towards the palm-fringed Carlisle Bay, a superb snorkelling spot, with clear water and fewer crowds. The bay is well sheltered, and has a really gorgeous beach, which has two very nice restaurants on it, East and Indigo.

Cruise 10nm north up to Deep Bay, a very secure and sheltered anchorage on the west of Antigua. The bay is famed for the shipwreck that lies at its entrance, a merchant vessel called the Andes, which sank in 1908. The tip of a mast is still visible above the water, and it’s worth a visit with the dinghy once you’re anchored. While you’re here, it’s well worth the easy hike up to the old Fort Barrington, which has superb 360˚ views of the surrounding coast, and is a wonderful place to watch the sunset. As this is a short leg, it’s worth stopping at Hermitage Bay for an extended lunch stop, where rumour has it Queen Elizabeth II once went swimming.

A longer sailing day takes you north from Deep Bay to Dickenson Bay, a great place to stop for lunch. The sweeping beach is scattered with hotels, bars and restaurants. Our favourites are Ana’s on the Beach, Sneaky Petes Beach Bar, and Coconut Grove. Then turn southwards and sail down to Jolly Harbour. An extremely well sheltered and well- equipped harbour, Jolly Harbour is home to a string of bars, and is a great place to stock up on provisions. There’s also a swimming pool, fuel dock and 18-hole golf course.

Otherworldly turquoise waters lap against pristine sands in this lovely anchorage just 2nm from Jolly Harbour. Today is a nice and gentle sail, and as this is a short leg, it’s worth stopping at Hermitage Bay for an extended lunch stop, where rumour has it Queen Elizabeth II once went swimming! The legendary Sheer Rocks bar sits on a hill at one end of the bay overlooking Coco Beach, and is blessed with sensational views of the sun dipping the horizon.

There’s time for one last day of sailing as you head back to English Harbour. The journey along the coast from Coco beach takes you past Ffryes Bay, a decent lunchtime anchorage. Once you're back at base, you should set off on a walk and climb up the hill to Shirley Heights – the views are well worth the effort! Shirley Heights really comes alive on Wednesdays and Sundays, when steel drum bands lead ‘jump up’ parties. You'll also be able to walk over from Nelson's Dockyard to Falmouth Bay, and gaze at the mega yachts across from the Antigua Yacht Club.