Big Boat racing in Barbados consists of the Offshore Regattas and the Round-the-Buoys Series, with the season running from January to July. The highlight of the sailing calendar is the Mount Gay/Boatyard Regatta, which takes place in the last weekend of May, or the first weekend in June.

Offshore Regattas take place on Sundays and races are set in Carlisle Bay and along the South and West Coasts of Barbados. This type of racing attracts the larger competitive yachts, and boats are divided into Racing and Cruising Classes. Different designs of boat are handicapped under the CSA Rating Rule, and include Benetau, Vanderstadt and DuBois, among others, as well as some locally designed boats.

The Round-the-Buoys Series tales place on Saturday afternoons and is a little more laid-back, with racing being confined to Carlisle Bay. The Series attract some of the smaller boats, though many boats sail in Offshore and Round-the-Buoys races. The format is staggered starts, and boats are handicapped using a performance rating that determines their start time. This start time may vary every week, and the first boat to cross the line wins. Apart from this handicap class, the Round-the-Buoys also consists of class racing, including Lasers, Optimists and catamarans.

Big Boat racing is organised by the The Barbados Yacht Club.