Antigua Sailing Itinerary: A 7-Day Crewed Week Around the Island

Your week begins at Nelson's Dockyard inside English Harbour, on Antigua's south coast — a 40-minute transfer from V.C. Bird International. Your captain and chef meet you at the dock with cold drinks and a chart briefing, walk you through the boat, and get your gear stowed. The dockyard itself is the briefing's backdrop: a restored 18th-century Georgian naval base of stone warehouses, sail lofts, and the old Admiral's Inn, still working, still berthing yachts, and a UNESCO World Heritage Site since 2016.

There's no rush to leave on day one. Most crews take a short shakedown sail the three miles around to Falmouth Harbour next door — a wide horseshoe bay where the season's largest yachts lie at anchor — or simply settle into Freeman's Bay at the mouth of English Harbour, where the swimming is good off the back of the boat and Galleon Beach is a tender ride away.

Late afternoon, take the climb up to Shirley Heights — the restored 1780s military lookout 490 feet above the harbour. The view down over English and Falmouth Harbours at golden hour is the postcard of Antigua, and on Sunday evenings the lookout turns into the island's long-running barbecue and steel-pan party. Dinner aboard tonight or ashore at the Admiral's Inn in the dockyard; the boat sits quiet on its chain in one of the most protected anchorages in the islands.

After breakfast aboard, your captain clears English Harbour and turns west along the south coast. The morning is an easy reach in the trades, the green hills of the interior rising to starboard and the open Caribbean to port. Antigua's south coast is a string of deep bays and headlands, and the sailing here is the gentle, sun-on-the-deck kind — a turn at the wheel if you want it, the foredeck if you don't.

The day's anchorage is Carlisle Bay, a curved white-sand bay backed by green hills on the south coast, fronting the discreet Carlisle Bay resort. It's a calm, protected spot for a lunch on the hook and an afternoon swim. The water is flat, the beach is long, and the pace drops the moment the anchor sets.

The afternoon highlight is just offshore: Cades Reef, a two-mile barrier reef running parallel to the south coast inside a marine reserve. It's the island's best snorkel — coral heads, reef fish, and clear water with almost no current. Your captain runs you out by tender or repositions the boat to drift the reef, then it's back to Carlisle Bay for sundowners and dinner aboard.

Today rounds the southwest corner of the island and heads up the leeward west coast — the calm, protected side, in the lee of the land and out of the swell. It's a short, soft sailing day with time to slow down. The west coast is where Antigua keeps its quietest anchorages, away from the harbours and the cruise traffic of St. John's further north.

The day's destination is Hermitage Bay and the cluster of anchorages around Five Islands Harbour — a string of secluded coves on the west coast fronting low green hills, with the exclusive Hermitage Bay resort tucked into one of them. The beaches here are quiet and the water is flat; some afternoons you'll share the bay with one or two other boats and no one ashore.

This is a deliberate rest day in the middle of the week — paddleboards and kayaks off the swim platform, a long lunch, an afternoon swim, and nothing on the schedule. Your chef provisions for a dinner aboard, the boat barely moving on its chain, the sun setting straight off the bow into the Caribbean on the island's west-facing side.

A short hop up the coast brings you to Deep Bay, one of Antigua's most rewarding anchorages and one of the few where the highlight is in the water you're floating on. In the middle of the bay, in about twenty feet, lie the masts and hull of the Andes — a wooden sailing ship that caught fire and sank here in 1905, fully loaded. The masts come close enough to the surface to snorkel, and the wreck has become a small reef of its own.

Above the beach on the northern headland stand the ruins of Fort Barrington, an 18th-century gun emplacement that guarded the approach to St. John's Harbour. The short walk up is worth it for the view back over the bay, the boat at anchor below, and the whole sweep of the west coast you've sailed.

Deep Bay is a calm, sand-bottomed anchorage with a good beach, so the day splits naturally between the wreck snorkel, the walk to the fort, and an afternoon in the water. Dinner aboard tonight with St. John's — the island's capital and its only real town — a short distance up the coast if you want to provision or step ashore.

The longest sailing day of the week takes you around the north of the island and into the North Sound — a shallow, reef-strewn corner of turquoise water and small uninhabited islands off Antigua's northeast tip. The route passes Long Island, home to the exclusive Jumby Bay resort, before threading into the Sound proper. Your captain will pick the line through the reefs; this is good-light, eyeball-navigation water, and all the better for it.

The anchorage is off Great Bird Island, a small wildlife sanctuary inside the North Sound National Park. It's a classic desert-island stop — no development, a short hike up to a ridge with a panoramic view over the Sound and its reefs, and the home of the rare Antiguan racer, once the world's most endangered snake, now recovering on the protected islets.

This is the wild, quiet end of Antigua — turtle grass and reef in clear shallow water, birds working the cays, and an anchorage that feels a long way from the harbours of the south coast. Swim, hike the ridge for the view, and have dinner aboard on the hook with the reef breaking gently in the distance.

Down the east coast today to Nonsuch Bay — a large bay on Antigua's windward side, sheltered from the open Atlantic by a barrier reef that runs across its mouth. Behind the reef the water goes flat and clear, and the sailing inside the bay is some of the prettiest of the week: protected water with a real breeze, the kind of conditions that make Antigua a sailor's island.

You anchor off Green Island, an uninhabited islet on the east side of the bay with a handful of small coves and white-sand beaches, almost nothing built ashore, and reef snorkeling straight off the boat. It's the windward coast's answer to the calm of the west — turquoise, breezy, and empty, with the Atlantic breaking white on the reef a half-mile off.

Spend the afternoon working the coves — a different beach for lunch, a snorkel on the reef, paddleboards across the flat water inside the bay. Nonsuch is also one of the Caribbean's best flat-water sailing and kiting venues for exactly the reason it's a good anchorage: steady trades, protected water. Last dinner aboard tonight in one of Antigua's quietest corners before the short run back to the dockyard.

A final morning on the hook at Green Island — a swim, a slow breakfast on the aft deck, a last snorkel on the reef — before lines off for the short reach back around the southeast corner of the island to English Harbour. It's an easy closing sail, the windward coast giving way to the familiar headlands of the south, and the dockyard opening up on the bow as you round into the harbour.

Charters typically disembark in the morning, so the last night is usually spent back at English Harbour or Falmouth, with a farewell dinner aboard or ashore in the dockyard. If the timing's right, one more climb to Shirley Heights closes the loop where it started.

Seven days, a full circle of the island, and not a single long passage — Antigua done the way the island rewards: under sail in steady trades, anchored somewhere different every night, and back to flat water by sundown.