Anguilla is not an island of monuments. It was too dry and too flat to make a plantation economy work, so it was never rich, and there is very little colonial architecture. What it has instead is older than that, and quieter.
Fountain Cavern National Park
A limestone sinkhole near Shoal Bay holding a freshwater spring that the Arawak used for at least a thousand years. Inside are petroglyphs and a stalagmite carved into a figure of Jocahu, the Taíno creator deity — one of the most important pre-Columbian sites in the Lesser Antilles. Access is restricted to protect it, so check locally before setting out.
Wallblake House
Built in 1787 and the only surviving plantation house on the island, in The Valley. The stone kitchen and stables survive alongside the main building. It sits beside St Gerard's Church, whose walls are laid with local stone and whose side openings are fitted with ships' timbers rather than glass.
Heritage Collection Museum
A private museum in East End assembled over decades by Colville Petty, running from Arawak artefacts through the salt industry to the 1967 revolution — the episode when Anguilla rebelled to stay British rather than to leave. Small, dense, and the best single explanation of the island you will find.
Sandy Ground and the boat yards
The harbour village is where Anguilla's racing sloops are built by hand, in the open, from wood. If a boat is under construction you can usually stand and watch. This is the island's living heritage in a way no museum is.
Big Springs and the salt ponds
Another Arawak petroglyph site sits at Big Springs in Island Harbour. The salt ponds at Road Bay and Rendezvous Bay were the island's main export industry until the 1980s and are now the best places for birdwatching — herons, egrets, stilts, and in winter, migrating waders.
The 1967 revolution
Anguilla's defining political event is barely known outside the Caribbean and inverts every expectation. In 1967 Britain grouped the island with Saint Kitts and Nevis into a single associated state. Anguillians objected, expelled the Saint Kitts police force, and declared themselves separate. Two years of negotiation failed and in March 1969 Britain landed paratroopers on the island — who were met by a population that wanted to remain British, not to leave. Anguilla got its wish and is a British Overseas Territory to this day. Anguilla Day on the 30th of May marks the start of it, and the story is told properly at the Heritage Collection Museum.