59th Annual
Summerset Regatta

This year CMCS is proud to present the 58th annual Summerset Regatta on the weekend of October 17-19, 2025.

In 1965, a few adventurous sailors placed a classified ad in the local newspapers looking for “Anyone interested in racing sailboats from Fort Myers Beach to Naples”. That first race led to an annual event that sailors in Southwest Florida look forward to each year – known as the Summerset Regatta. This was also the genesis of the racing program for Caloosahatchee Marching and Chowder Society (CMCS), now in our 51st year of operation. Today, sailors from Charlotte Harbor to Marco join in the fun of racing and cruising. Yachts race in Saturday’s buoy races and Sunday’s distance race(s) in the Gulf of Mexico near Fort Myers Beach.