The Leeward Islands carry more history per square mile than almost anywhere else in the Caribbean. English, French, Dutch, and Danish colonial powers all fought over these islands for two centuries; the forts, dockyards, and estate houses they left behind are among the finest examples of colonial-era military architecture in the Atlantic. Add the natural drama of Nevis Peak and Montserrat's active volcano and a week in the Leewards provides more content than a fortnight anywhere else in the region.
Nelson's Dockyard, English Harbour, Antigua
The only continuously functioning Georgian naval dockyard in the world — a UNESCO World Heritage Site. The dockyard was built in the 1740s and served as the main British naval base in the eastern Caribbean until 1889. The Admiral's Inn, the Copper and Lumber Store, the Pillars of Hercules capstan house, and the boat sheds are all original 18th-century buildings, most now converted to hotels, restaurants, and marina offices. Horatio Nelson served here from 1784–87 and hated every minute of it (he described Antigua as "this infernal hole").
Entry to the national park is around US$8; the dockyard museum within is free. Allow a full morning to explore properly. The dockyard is accessible from the charter base at Falmouth Harbour — walk over the hill (20 minutes) or take the dinghy around the headland.
Shirley Heights Lookout, Antigua
The hilltop fortifications above English Harbour offer the finest view in Antigua — the entire south-west coast, both harbours, and on clear days the island of Guadeloupe to the south-east. The Sunday evening barbecue at Shirley Heights has been running for decades: steel band from 1500, reggae from 1900, and a reliable crowd of sailors from the anchorage below. The military fortifications themselves — powder magazines, gun platforms, and the remains of a signal station — are worth exploring during the day when they are mostly empty.
Brimstone Hill Fortress, St Kitts
A UNESCO World Heritage Site on the south-west coast of St Kitts: a complete British artillery fortress built between 1690 and 1790 on a volcanic plug 244m above the sea. The fortress was known as the "Gibraltar of the West Indies" — it commands the entire south-western approaches to the island and, on a clear day, seven other islands are visible from the battlements. The magazine, barracks, infantry quarters, and officers' quarters are all intact. Entry around EC$25. Taxi from Basseterre (the main port, 10 miles) or from the cruise ship pier at Port Zante.
Nevis Peak Trail
Nevis Peak (985m) is the dominant geographical feature of the island — a near-perfect volcanic cone rising from the sea, usually wreathed in cloud at the summit. The trail from the source spring on the south-east slope to the summit takes 4–5 hours return and requires a local guide (the trail is poorly marked above the cloud line). The views on clear mornings — before the trade wind clouds build — encompass St Kitts, Antigua, Montserrat, Guadeloupe, and Statia. The guide service operates from Nevis under the Four Seasons nature programme; book in advance.
Alexander Hamilton's Birthplace, Nevis
The founding father of the United States' financial system was born in Charlestown, Nevis in 1755. The Museum of Nevis History occupies the restored house — a modest two-storey building on the waterfront — and contains the most comprehensive collection of Hamilton artefacts outside the United States. The museum is small but well-curated; the ground-floor rooms have been restored to 18th-century appearance. Entry around EC$10. Located in Charlestown, accessible from the anchorage at Pinney's Beach by dinghy at the town dock.
Frequently Asked Questions
Q: When is Nelson's Dockyard least crowded?
A: Early morning on weekdays outside Antigua Sailing Week (late April). The dockyard fills with charter crews in the afternoon and with race spectators during Sailing Week. A 0800 visit gives you the buildings largely to yourself.
Q: Is the Montserrat Volcano Observatory accessible from the sea?
A: Yes — anchor at Old Road Bay on the north-west coast and take a taxi from the jetty to the Observatory (approximately 15 minutes). The MVO runs guided tours of the observation deck with views into the exclusion zone and the lava dome. Check the MVO website for current exclusion zone boundaries before approaching the south of the island by sea — the zone extends offshore.