Sailing Antigua: 7 Days in the West Indies

Home to some of the most spectacular sailing events in the Caribbean, from Antigua Sailing Week to the Antigua Classic Yacht Regatta, Antigua brims with white-sand beaches and deserted coves straight from your sailing daydreams. Blending natural splendor and centuries-old sailing culture, the island is a must-see for experienced sailors and first-timers alike.

Below, a one-week sailing itinerary highlighting some of the island’s most sought-after stopping-off points. After landing on the northern coast with Tradewind Aviation, your first destination is one of Antigua’s most famous.

Day 1: English Harbor

Framed by towering fortresses and sweeping beaches, English Harbour exudes naval history as the founding place for the Royal Navy’s Caribbean fleet in the eighteenth century. A day in the harbor puts you close to fascinating outposts like the restored marina Nelson’s Dockyard and the restored military lookout Shirley Heights, a UNESCO World Heritage Site.

Step inside Admiral’s House Museum – also in Nelson’s Dockyard National Park – to learn about the importance of the dockyard in Antiguan and Caribbean history, then climb up to Shirley Heights Lookout for one of the most iconic images of Antigua: English Harbour and Falmouth Harbour at sunset. The former military base has been converted into a restaurant and bar and is the perfect place to end the day on Sundays with an evening party and live steel drum band.

Day 2: Nonsuch Bay

Your first day on the open water takes you to Nonsuch Bay, about eight miles northeast of English Harbour. On the way, you will pass Half Moon Bay Beach, one of Antigua’s most beautiful shorelines and snorkeling destinations, and York Island, which should be given a wide berth when sailing. Protected by a windward barrier reef, the secluded Nonsuch Bay is the perfect place to anchor for the night.

Near the edge of the bay, the uninhabited Green Island is a favorite among sailors who frequent Antigua with its tranquil white-sand beaches, lush greenery, and variety of exotic birds onshore.

Day 3: Great Bird Island

Quiet and serene, Great Bird Island off of Antigua’s northeastern coast is both a spectacular beach escape and a 20-acre sanctuary for endangered wildlife like red-billed tropicbirds, West Indian whistling ducks, frigates, and rare lizards.

As you sail from Nonsuch Bay to the island, you will spot Devil’s Bridge – a natural arch carved by the sea – and Mercer’s Creek Bay, home to Stingray City Antigua, along your route. Once anchored, explore the destination’s vibrant coral reefs and take a hike to the top of the island for exceptional views of the surrounding North Sound National Park.

Day 4: Dickenson Bay

One of the most beautiful and popular locales on the island, the white-sand beaches of Dickenson Bay are home to many of Antigua’s high-end resorts, along with restaurants, shops, and adventure activities. Pass Prickly Pear Island and Jumby Bay Resort on Long Island to reach the lively enclave, then spend your time soaking up local culture, windsurfing, and horseback riding on sugary white-sand beaches.

Overlooking the picturesque shoreline, casual elegant eateries like Ana’s Restaurant and Art Gallery and Coconut Grove beckon, and just outside of the bay, there are a few uninhabited islands that are worth a snorkeling trip for their one-mile-long coral reef brimming with diverse marine life.

Day 5: Deep Bay

Not far from Dickenson Bay, take a short sail past Fort James and St. Johns (the capital of Antigua) to anchor in Deep Bay. With protected waters and a hundred-year-old shipwreck in the middle of the bay, the destination is ideal for snorkeling. Onshore, pristine beaches are the perfect place to sunbathe – but offer little shade – and interesting hikes abound in the surrounding landscape. Walk to the tip of the cape to take in the boundless ocean at sunset, and hike ten minutes north to the hilltop Fort Barrington to go back more than 200 years in history and enjoy sweeping vistas of the island.

Day 6: Jolly Harbour

One of Antigua’s most well-known destinations, Jolly Harbour welcomes sailors to a bustling marina, a one-mile long shoreline that is perhaps the widest on the island, and some of the island’s best restaurants. After sailing past Five Islands and reaching the marina, spend your day indulging in freshly caught lobster and coconut shrimp at outposts like The Nest Beach Bar and Restaurant (on the neighboring Valley Church Beach) and swimming in the shallow waters of Jolly Beach, or plan for an afternoon at The Jolly Harbour Golf Club, an 18-hole championship course.

Day 7: Falmouth Harbour

Complete your journey close to where you began in Falmouth Harbour, a horseshoe-shaped bay on the southern coast featuring three expansive marinas and a boatyard. The hub for Antigua’s yachting community can be reached by passing Cades Reef – where snorkeling the inner reef may bring you face to face with stingrays and harmless reef sharks – and Carlisle Bay Antigua. Once docked alongside Antigua’s luxury yachts in the harbor, take a dive in the bay to explore the iconic Pillars of Hercules underwater. If you need to head back to the neighboring English Harbour to wrap up your trip, simply head around the point.