Rags To Riches Regatta

6.27.26

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.

What started as a lighthearted local tradition has grown into a symbol of Grayton’s unique charm and coastal culture. But like any good tradition, it takes a community to keep it going.

We’re asking for your support to help fund this year’s Regatta — from event logistics and safety crews to prizes and refreshments. Every donation, big or small, helps ensure this iconic event remains free and fun for all, while preserving the spirited legacy of Grayton Beach.

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 26th at Chiringo Grayton, and at the Grayton Beach Tent on Raceday.
Wristbands include AYCD Odd Pelican Beer & Palm Folly Seltzer available at the Palm Folly Tent on Raceday.
Raffle Tickets are available for purchase online, and at the Kickoff Party. You do not need to be in-person to win raffle prizes.

Schedule of Events

Check-In: 8 a.m. – 9:30 a.m.

Skippers Meeting: 10:30 a.m.

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 June 28th or check the Grayton Beach Instagram Page.

History of R2R Regatta

Grayton Beach’s Rags To Riches Regatta’s dates back forty-plus years to 1981 when a group of sailors in Grayton Beach made plans for a friendly competition to be held on July 4th. With a buy-in of $20 per Captain, and a Winner-Take-All purse, the pot wasn’t the real prize. The prize was bragging rights amongst friends, a cool t-shirt, and an ice-cold beer waiting at the finish line. The tradition continues today as 30A locals and visitors gather to cheer on teams as they navigate 16-foot Hobie Cats in the race from Grayton Beach (originally known as the “rags” side of town) to Seagrove (then known as the “riches” neighborhood), while raising money to support our South Walton Artificial Reef Association (SWARA).

With an aesthetic steeped in “old money” coastal luxury—think sun-faded polos, vintage Ray-Bans, and nautical grace—Rags To Riches embodies the golden age of beachside leisure. The event’s name tells a story of journey and transformation, from humble beginnings to sun-drenched sophistication. Whether you’re navigating the swells or spectating with a spritz in hand, this regatta offers a refined nod to classic coastal culture.

Join us as Grayton Beach comes alive with heritage, camaraderie, and the art of the sail.

Rules & Regulations:

The race schedule is subject to change based upon weather and other conditions the day of the race. The final schedule, race course, and other important details will be communicated at the Captain’s meeting on the day of the race. Check back with www.ragstorichesregatta.com for information about getting your boat on the beach. The regatta will be governed by the Rules as defined in the Racing Rules of Sailing (RRS) and GYA regulations for sanctioned events (available at www.gya.org).

ELIGIBILITY

The regatta has principally attracted Hobie 16 beach catamarans. Similar boats are welcome to participate and the race judges will attempt to performance-rate all boats. This however is not an officially sanctioned Hobie (or other) race. The performance rating will be done if possible with the primary goal of a safe, fun, and equitable race.

SAFETY

All boats will comply with United States Coastguard and State safety regulations. It is the responsibility of each skipper to determine whether they should start a race, continue a race, or if lifejackets are appropriate. This does not supersede any class regulations that may require the wearing of lifejackets while on the water.

SUPPORT BOATS AND SAFETY PERSONNEL

Support boats and jet skis will be provided to assist at launch and landing. Security and safety personnel will also be available to assist as needed.

CHANGES TO RACING RULES

The Sailing Instructions may change some of the Racing Rules of Sailing. Any changes will not require prior knowledge by the competitors.

SAILING INSTRUCTIONS AND COURSE

Final sailing instructions will be provided during the Captain’s meeting.
The race instructions are generally as follows (subject to day of race weather and surf conditions):
A Le Mans style start: Participants will launch their boats from the beach, the starting line. Depending on the number of boats participating, the race times may be adjusted to give consideration to the varied start times if all boats are not able to launch off the beach at the same time.
The first leg will consist of sailing west to a buoy approximately 1/2 mile away. The turn will require the buoy to be passed on the port side.
The second leg will be approximately 3 miles to a buoy placed near Seagrove, due east from the start at Grayton. The turn will require the buoy to be passed on the port side.
The third leg will be approximately 3 miles back to the west to the first buoy. The turn will require the buoy to be passed on the starboard side.
The final leg will be approximately 1/2 mile back to the east to a water line finish that will be marked on the beach. Boats must cross the finish line within 100 yards of the beach.