Rags to Riches Regatta

The 29th edition of the annual Rags To Riches Regatta returns to Grayton Beach on Saturday, June 27. The small catamaran race is a tradition among SoWal sailors, families, friends, and Grayton Beach lovers. Come out to watch the regatta take off from the shores of Grayton Beach as they race to Seagrove Beach and back to Grayton.

Schedule of Events:
Crooked Island Captain’s Party: 
Friday, June 26 | 5PM – 7:30PM at Chiringo Grayton
RACE DAY:
8AM – 10AM : Boats Transported onto the Beach by Official Permitted Vehicles
11AM: 29th Rags to Riches Regatta Race

Born on the beaches of Grayton Beach in 1981, the Rags to Riches Regatta is more than a race—it’s a living piece of South Walton history. What started as a laid-back Fourth of July challenge between local sailors has grown into one of the most beloved traditions along 30A. ragstorichesregatta.org