The first race, Old Road, started with winds gusting up to 35 knots but all sailors returned back safely with smiles on their faces as everyone is so pleased to be back on the water after two years of postponements . Winners in their classes were the beautiful 114' staysail schooner Aschanti IV, the classic 36' sloop Alani sailing in her first Classics, traditional Carriacou work boat Genesis, vintage 1936 Seefalke II, spirit of tradition 91' yawl Bequia, the tall ship class 157' staysail ketch Chronos and the historic class 44' LJ Windward . 

The dragon challenge was held in Falmouth Bay due to the sea state outside the harbour. Seven of these Olympic class 29' one design keel boats closely competed against each other with the 2019 winner Rocco Falcone representing Antigua Yacht Club successfully defending his challenge against New York, Cortina Italy, Mill Reef Antigua, Monaco and St Maarten yacht clubs.