2. August Monday Boat Race
Today you will have to get into the water and follow the boat race at Sandy Ground, which typically includes 15 boats representing the island’s villages. Hundreds more boats will be in the water, filled with locals debating about who will win. The banter you will hear will be endless, and classically Anguillan. No matter what, an Anguillan will defend his boat. It’s a long race, so bring a hat and something to drink.
Guaranteed, the party back on the beach is the biggest of the year in Anguilla. You will see people in the water and on the beach all afternoon, and the fete goes all night, with live music on the beach. The best place to be for these times will either be in your own yacht in the bay, or over by Pump House or Johnno’s Bar, where all the action will be.