Antigua is the sailing capital of the Caribbean. English Harbour — one of the finest natural anchorages in the world and Nelson's base for the entire Leeward Islands during the Napoleonic Wars — is surrounded by restored Georgian dockyard buildings and has enough charm to justify two days before you even leave the harbour. The Leeward Islands to the north and west — Barbuda, St Kitts, Nevis, Montserrat — offer a week of island-hopping that mixes Caribbean tourism with genuine remoteness. Coastal Skipper level experience is recommended for the inter-island passages.
Day 1: English Harbour — Arrival and Exploration
Nelson's Dockyard, restored by the National Parks Authority and now a UNESCO World Heritage Site, occupies the southern shore of English Harbour. The Copper and Lumber Store Hotel within the dockyard is one of the most atmospheric places to eat in the Caribbean — book ahead. The Pillars of Hercules restaurant on the headland above Galleon Bay has the best view of the harbour entrance.
Falmouth Harbour, adjacent to English Harbour, has the main charter marinas and provisioning. Budget Supermarket on the main road near the marina roundabout has the best prices in Antigua.
Day 2: English Harbour to Barbuda — Codrington Lagoon
Barbuda is Antigua's flat, sparsely populated sister island — 62 miles north and a world apart. The Codrington Lagoon on the west coast is accessible through a shallow channel (carry tide tables — the entrance bar has 1.5m at high water). Inside, the lagoon is one of the Caribbean's finest bird sanctuaries: the largest frigate bird colony in the western hemisphere nests here, with up to 5,000 birds present. Anchor in the lagoon or take a mooring buoy from the warden. The beach on the north coast — Pink Sand Beach — justifies the passage.
Weather note: The passage to Barbuda crosses open water north of Antigua. In strong trades (above Force 5) it is a rough beat; time the passage for lighter conditions in the morning.
Day 3: Barbuda to St Kitts — The Channel
St Kitts is 50 miles north-west of Barbuda — a long day in the trade wind, but the passage is on a reach and the island's volcanic silhouette becomes visible from 30 miles out. Basseterre, the capital, has a restored colonial waterfront and a busy rum bar scene. The Majesty Casino on the southern waterfront is not recommended, but the cricket pitch in the centre of town (the Warner Park Cricket Ground) is worth a look. Anchor in Basseterre Roads or berth at Port Zante cruise ship terminal when the big ships are absent.
Day 4: St Kitts — Narrows Channel to Nevis
The Narrows between St Kitts and Nevis is a two-mile channel with consistent 20-knot trade winds and a short chop — exhilarating sailing, over in 30 minutes. Anchor at Pinney's Beach on the west coast of Nevis, one of the finest Caribbean beaches — palm trees, dark sand, the Four Seasons resort visible in the distance (eat there for dinner if the budget allows; the beach bar is open to non-guests). The Nevis Peak volcano rises 985m from the beach — walk the trail to the summit for views across the Leewards.
Day 5: Nevis to Montserrat
Montserrat is the most unusual island in the Leewards — the Soufrière Hills volcano erupted in 1995 and destroyed the southern half of the island, including Plymouth, the capital. The exclusion zone covers the south; Little Bay in the north is the new settlement and main port. Anchor off Little Bay or at Old Road Bay in the north-west. The Montserrat Volcano Observatory above Brades offers guided tours with views into the caldera and the buried capital. A genuinely extraordinary place.
Day 6: Montserrat to Antigua — Jolly Harbour
The return passage to Antigua takes 4–5 hours in the trade wind on a broad reach. Jolly Harbour on the west coast of Antigua is the alternative to English Harbour — a purpose-built marina complex with a supermarket, restaurants, and full services. Less atmospheric than English Harbour but more practical for provisioning. Anchor in Jolly Bay outside the marina if no berth is available.
Day 7: Jolly Harbour to English Harbour
A final passage south along the west coast and around the southern tip of Antigua to English Harbour. Stop at Curtain Bluff on the south coast — a headland with a small anchorage and one of the finest views on the island — before returning to Falmouth for the handover. Allow two hours for the formal return and handover process.
Frequently Asked Questions
Q: When is Antigua Sailing Week?
A: Late April or early May each year. Antigua Sailing Week is one of the world's oldest and largest offshore racing events — over 100 boats, five days of racing in the waters around English Harbour. Berths and anchorage space are extremely limited during Sailing Week; either book months in advance or plan around it.
Q: Do I need to clear customs at each island?
A: Yes — Antigua, Barbuda, St Kitts and Nevis, and Montserrat are all separate jurisdictions for entry purposes, even though they are close geographically. Keep crew passports and ship's papers accessible. The paperwork is straightforward but takes time at each stop.