Every Caribbean island has a sport. Anguilla's is boat racing, and it is not a tourist attraction that happens to involve locals — it is the other way around.
Where it comes from
Anguilla had no plantations worth the name and no export crop, so for two centuries its men went to sea: to Santo Domingo to cut cane, to the Dominican Republic, to Curaçao's refineries. They sailed there in wooden sloops built on the beach at Sandy Ground, and the race home was a matter of pride. When the schooners stopped running, the racing stayed.
The boats
Anguillian racing sloops are built by hand from wood, without plans, by boatwrights who learned from their fathers. They carry no engine and no deck — the crew sits on the windward rail and shifts sandbags and stones as ballast when the boat turns. Hulls run from around fifteen to twenty-eight feet, and the sail area is enormous for the size. Boats are owned by villages and families, and the names — De Chan, Real Deal, Light and Peace — are known to everyone on the island.
When to see it
The season runs from Anguilla Day at the end of May through the Summer Festival in August, with the biggest races in carnival week. Anguilla Day itself features the round-the-island race, which starts and finishes at Sandy Ground and takes most of the day.
How to watch
Sandy Ground is where the starts and finishes happen and where the crowd gathers. There is no ticket and no grandstand: people stand on the beach with a drink, and the bars run all day. Ask which boat is favoured and you will get a long answer. The races are followed with a seriousness that surprises visitors — this is the closest thing Anguilla has to a national institution.
How a race works
Boats start from the beach rather than from a line at sea — crews push off together on a signal, which makes the first minutes chaotic and decisive. Courses run out to a marker and back, sometimes several times, and take from ninety minutes to a full afternoon for the round-the-island race. There is no handicap system worth the name; boats are grouped by size class and the rest is crew and local knowledge of the wind behind the headlands.
Where the boats come from
Sandy Ground and Island Harbour are the two building villages. A new sloop is a community project, funded by subscription and built in the open over months. If you pass a hull under construction on the beach, stopping to look is entirely normal and the builders will usually explain what they are doing.