The Anguilla Summer Festival runs for around ten days from the end of July into the first week of August. It is the island's carnival, and it is built around two things at once: the calypso and masquerade tradition of the wider Caribbean, and the boat racing that is particular to Anguilla.
The boat racing
Carnival week is the peak of the racing season. Races run most days from different beaches — Sandy Ground, Meads Bay, Rendezvous Bay, Island Harbour — and the August Monday race is the one everybody attends. Crowds line the beach from early morning and the bars open with them.
The carnival calendar
- Calypso competitions — heats through the week, with the Calypso Monarch final the highlight; songs are written for the year and comment sharply on local politics.
- J'ouvert — the pre-dawn street procession that opens the main days, with paint, powder and music trucks from around four in the morning.
- Parade of Troupes — costumed bands through The Valley in the afternoon heat.
- Miss Anguilla — the pageant, taken more seriously than visitors expect.
Getting around during festival
The Valley and Sandy Ground both become impassable by car on the main days. Taxis are in demand and prices rise; arrange a driver in advance or plan to walk. Accommodation books out well ahead, and the ferry from Sint Maarten runs busier than usual.
What it feels like
Anguilla has around fifteen thousand people, and during festival it feels as though all of them are in the same place. This is not a performance staged for visitors — the troupes, the calypso and the boats belong to the villages, and the whole island turns out. Come with no schedule and follow the crowd.
Where it came from
The festival dates to 1974 and merged two traditions: the August Monday celebration of emancipation, observed across the British Caribbean since 1834, and the boat races that Anguillians had been running from the beaches for far longer. That is why the calendar mixes calypso and masquerade with a sailing regatta — most other islands celebrate one or the other.
Practical advice for visitors
Book accommodation months ahead; the island fills with Anguillians returning from abroad. Carry cash, since the stalls and bars do not take cards. Sun protection matters more than you think — the parade runs through the hottest part of the afternoon and there is almost no shade in The Valley.