What started as a shared passion for the sea has grown into one of Anguilla's most iconic events. Anguilla Poker Run sends participants beach-hopping by boat across five stunning stops, each with food, music, and pure island energy — kicking off at Johnno's Beach Bar with breakfast and building from there. Part race, part party, part celebration of life on the water, the Poker Run draws boating enthusiasts from across the region every August as part of the Anguilla Summer Festival. Expect a bikini contest, adrenaline, and the kind of day that stays with you long after you leave the island.