2023 Flip Flop Regatta
Welcome to the 2023 Flip Flop Regatta Information page.

Dear Friends of Courageous;

The Flip Flop Regatta is back Sat. Aug. 12th!  One of the largest New England regattas of the season, FFR is a pursuit style race starting in Broad Sound, around the outer harbor islands and back to the finish in Boston Harbor. It’s a fun and competitive race for all - no handicap certificate? No problem! We'll get you a rating for the race - liveaboards and 1st time racers are welcome.  

Your entry fee and all proceeds support Courageous Sailing's youth programs and further our mission of transforming children's lives through sailing programs that inspire learning, personal growth, and leadership.

Becoming a Skipper Sponsor is a great way to support Courageous by potentially doubling your contribution. If your employer has a matching gift program for qualified 501(c)(3) nonprofit organizations, submit the receipt from your Sponsorship along with the completed sponsorship form (download from the information page) to your company. All details, NOR, SIs, etc. will be posted on Regattaman.

If you are unable to race but you or your crew would still like to support Courageous: Donate here.

With Pier 4 still closed for repairs, we will again have a post-race gathering at Pier 6 Restaurant in the Navy Yard starting at 16:30, awards at 18:00. Light apps will be served, cash bar. 

Your participation and donation will help Courageous be there for the kids who need our programs more than ever, especially while our pier is being repaired.

Thanks for your continued support, and hope to see you on the race course Sat. August 12th!

Dave Alexander                          Dave Di Lorenzo
Board President                         Executive Director 


Sat : Aug 12

(Registration Not Open)

Thu Aug 10, 2023 : 15:36

Notice #1- Skipper's Meeting And Start Times

We are just two days away from the 2023 Flip Flop Regatta! As of this afternoon, we are up to 48 boats and counting, and the weather is looking great, though we’re crossing our fingers for a little more breeze. It’s not too late to register - we are accepting entries until 17:00 Friday Aug. 11th, so spread the word! Some details for the event: 

Skipper’s Meeting:

When: Friday 11 August,  18:00 

Where: In Person: @ Courageous Tent on Pier 3, Boston Navy Yard

Parking: Street parking or validated (small discount) parking @ The Nautica


Pizza and beverages will be available 

Online link: Here  (BYO pizza and beverages…..)

We will review SIs, scratch sheets, hang out skipper’s bags, and answer any questions for new participants. If you can’t make the skipper’s meeting in person, join online and pick up your skipper’s bag at the awards ceremony at Pier 6 Restaurant after the race. 


  1. As the current forecast is looking light, start times will not be posted until 09:00 the morning of the race. This will allow the RC to make the call between Random Leg Light and Random Leg Medium ratings as close to race time as possible. Please triple check your starting times Saturday morning for both courses - print / download / write your start times on the back of your hand. RC will not be able to give you start times on the water. 

  2. NOR and SIs are live on FFR Regattaman page - please download and review. 

  3.  Notifications: All additional notices will be posted on Regattaman Here

  4. Spirit Award - This is a fun race - dress up, decorate your boat, grill while you’re racing (okay, don’t do that…..) and go for the 2023 Flip Flop Spirit Award! 

Post-Race Gathering / Awards:

Where: Pier 6 Restaurant, Pier 6 in the Navy Yard.
When: Post-race, 16:30 - 19:30. Light apps will be provided, cash bar. Award ceremony will start at 18:00. 

Dockage: Pier 4 is still being repaired, so we cannot offer any dockage. Check NOR for list of nearby marinas. 

Lastly, a huge thank you to all our Skipper Sponsors….. if you haven’t done so yet, please help us do what we do for Boston’s kids by donating to Courageous. We’ll have a Venmo QR code at the awards ceremony, or you can click Here

See you Saturday! 


The Courageous Flip Flop Race Committee


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