The racing events are perhaps the backbone of the regatta. The original regattas evolved around the sailboat races. There are now two race events, held on two different days. One is an around the buoys race within Elizabeth Harbor and the second is an around Stocking Island race where the boats leave the harbor via one of the cuts, sail out into Exuma Sound, and return via the other cut.

The races are open to all sailboats and they are separated into classes by the race committee. There is a multihull class and several mono-hull classes. PHRF ratings are given out by the race committee to all boats in an attempt to even things out. There is perhaps no prettier sight than to see some three to four dozen beautiful sailboats under full sail in a fresh breeze in Elizabeth Harbor.

In 2008, sailboat racing in George Town has taken on a new look with pre-regatta sailing events including buoy racing in the harbor, a cruise race to Long Island, a fifteen mile ocean race, and seminars on sail trim and rules of racing.