Rags to Riches Regatta - 30A


Rags to Riches Regatta

Saturday, July 1, 2023 • Grayton Beach, Florida

Benefiting South Walton Artificial Reef Association (SWARA)

The Rags To Riches Regatta’s history dates back forty years to 1981 when a group of sailors in Grayton Beach made plans for a friendly competition to be held on Independence Day. Each Captain contributed a $20 buy-in, but the prize wasn’t the pot. 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).

The 26th annual Rags to Riches Regatta 2023 is presented by Crater Train Brewing Company and The 30A Company. Additional support is provided by our 2023 sponsors including 30A Shine On LivingBerkshire Hathaway HomeServices Beach Properties of FloridaPalm FollyDive 30AChiringoSage and Dragonfly3rd Planet Brewing CompanyHotz Coffee, Jake’s Beach Service, and YOLO Board + Bike.

Saturday July 1, 2023 – 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 July 1st.


An entry fee of $45 per boat will be collected for each registration, with fees donated to support SWARA. Spectators are also encouraged to join the festivities on the beach. 

To register your boat for the race make a $45 donation HERE. You can also purchase a spectator’s ticket by make a $25 donation HERE

Click here to check out the notice of Race. There will be giveaways from our local partners, and official Rags To Riches Regatta shirts will be available for purchase, with original art design by Chris Coleman. Beverages will be provided for a donation of $25 with a spectator’s wristband. Awards will be presented for 1st, 2nd, 3rd place finishers. The Captain and crew for each boat registered will receive a t-shirt and wristband for beverages on the beach.

Check out the official 2023 race shirt!

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).


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.


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


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


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.


Presenting Sponsors

core Sponsors


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