Now celebrating its 29th anniversary, the Rags 2 Riches Hobiecat Regatta returns to the iconic shores of Grayton Beach, Florida for a day of timeless tradition and spirited competition. Against a backdrop of emerald waters and old Florida charm, a fleet of Hobiecat sailboats will race with elegance and adrenaline from the white sand toward glory.
$1,000 Cash Prize
Donate today by purchasing a Hat, Shirt, Wristband, or Raffle Ticket and help us keep the wind in our sails, and raise money for South Walton Artificial Reef Association (SWARA).
Hats & Shirts available to pickup at the Kickoff Party on June 27th at Chiringo Grayton, and at the Palm Folly Tent on Raceday.
Wristbands include AYCD Palm Folly available at the Palm Folly Tent on Raceday (10AM – 2PM).
Raffle Tickets are available for purchase online, and at both the Kickoff Party and Raceday events. You do not need to be in-person to win raffle prizes.
First Warning: 10:55 a.m.
Race Begins: Immediately after
Awards Presentation & ‘Hanging with the Hobies’: 1 p.m.
NOTE: The timing of race-day events will be determined based on the weather conditions. To obtain the most accurate and up-to-date information regarding the Race Start and Finish, we request that you visit the Rags to Riches Registration tent on July 1st or check the Grayton Beach Instagram Page.

Sign up for beach news and local updates—plus a chance to win a $500 30A gift basket. One winner each month!