Sail for a change

The Flip Flop Regatta

One of the most popular pursuit races in New England returns in 2019!

August 10th, 2019

Courageous Sailing, Pier 4

Event Overview

Since 2003, the Flip Flop Regatta has been a highlight the Boston sailing calendar - a big boat pursuit race that begins in Broad Sound, heads out and around the Brewsters, then back past Deer Island and typically finishing in the Inner Harbor just off the airport. Many visiting racers then head straight to Courageous’ Pier 4 in Charlestown to tie up, relax and enjoy the after-party, usually one of the best and biggest Boston Harbor-side parties of the summer.


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Event History

The Flip Flop Regatta has been near and dear to the Courageous Sailing family since its founding in 2003, in memory of Ally Zapp. The regatta supported the efforts of the Ally Foundation to end sexual violence through science and innovation through 2013. After a hiatus for the Barefoot Regatta in 2014, the Flip Flop Regatta supported Boston-area youth sailing programs. For the first time in 2018, Courageous Sailing will run the regatta and after-party, and all proceeds will go directly to support Courageous kids - providing more opportunities for kids from low income families to participate in Courageous’ summer programs.


Regatta Registration

Join the regatta! Registration includes after-party tickets.

Sign Up Now

After-Party Tickets

Join the party after the regatta, no sailing required.

Make-A-Mark Partnerships


Live & Silent Auctions

Generous donors provide a wide range of auction items. 100% of proceeds benefit Courageous Youth Programs.

Download the Auction Donation Packet

Food & Drink Donations

Each year, Boston-area catering and beverage services provide delicious tastings, refreshing cocktails, and a selection of beer and wine.

Download the Food & Drink Partner Packet

Make-A-Mark Partnerships

Individuals and companies can directly support Courageous Kids this year by making a financial contribution at Make-A-Mark.

Download the MAM Partner Packet

Event Information

Who will the proceeds benefit?
Courageous Sailing teaches sailing and life skills free of charge to over a thousand of Greater Boston's children. We use sailing instruction to teach key leadership competencies, personal responsibility, communication, teamwork, problem-solving, and stewardship. All proceeds from the Flip Flop Regatta will fund the youth sailing and leadership programs.

Who will be there?
Members, neighbors, volunteers, parents, young professionals, sailors from throughout the region, and anyone who wants to have a blast while supporting Courageous Sailing.

Do I need to race to attend the tent party?
You do not need to participate in the race to attend the party. Some part tickets are included with regatta registration. If you need additional crew tickets, they may be purchased ahead of time. Non-crew tickets may also be purchased ahead of time or in person on the day of the event. Capacity is limited, so we suggest buying ahead, especially for large teams or groups!

Are there ID requirements or an age limit to enter the event?
There is no age limit to enter the event. Drinks are available for guests over the age of 21. Proper identification is required to receive your drink wristband.

What are my transport/parking options getting to the event?
Parking is available at the Flagship Wharf parking garage, located at 197 8th Street, Boston, for $13 if you arrive after 5 pm and depart before midnight, as well as at the Nautica parking garage, located at 88 Constitution Road, Boston, for $10 with validation. Please note, vehicles are not allowed to park or make drop-offs on the pier. Click here for a map with directions.

Where can I dock my boat?
Boats that participated in the regatta must arrange for dockage ahead of time. Reserve your spot through Regattaman.

What can/can't I bring to the event?
There is no place to store your personal belongings, so only bring what you will need. There is ample space under the tent, but keep in mind that this is an outdoor event, so please check the weather forecast and dress accordingly.

Where can I contact the organizer with any questions?
General inquiries can be directed to Lauren Saalmuller at Courageous Sailing. Contact Lauren at (857) 452-1766 or

What if I would like to pay via cash or check?
Please send an email to our office manager, Jacob Breslin, at detailing your interest in paying with cash or a check. You will then be added to the guest list and receive direction on how to pay. We apologize for any inconvenience.

Do I have to bring my printed ticket to the event?
Printed tickets that were purchased online are not required for individual ticket purchases. Crew tickets included with registration will be distributed during registration for the regatta and should be presented at the check-in table when you arrive at the event.

What is the refund policy?
There are no refunds available.