Welcome to the Rags to Riches Regatta, Grayton Beach’s most iconic and spirited sailing tradition. Held annually on the Saturday before the 4th of July, this one-of-a-kind race invites adventurous skippers to chart a course from the “rags” of Grayton to the “riches” of Seaside — and back again.

Whether you’re a seasoned sailor or just testing the waters, this friendly but fiercely fun regatta is all about community, celebration, and a little healthy competition on the Gulf. The course is short, the stakes are low, and the bragging rights? Priceless.

Entry includes:

1. Participation in the Regatta

2. Commemorative race shirt for both team members

3. Access to pre-race skipper’s meeting

4. A front-row seat to one of the most beloved traditions on 30A

Space is limited, so register early and get ready to sail your heart out in true Grayton style with the winner receiving $1,000 in Cash. Winner will also receive Team Name on the Rags To Riches Plaque that remains at Chiringo Grayton, year round.