Each year individuals from businesses around Boston support the Courageous Sailing Summer Youth Program by racing on a company-sponsored boat. 

2014 Teams


2014 Results


2014 Recap 

Evening Racing

With 6 total nights of racing in 2015, plus catered food and drinks after.

Monday nights in late May and June, seasoned and novice racers alike set sail off of Pier 4 in the Charlestown Navy Yard for some fast-paced, college-style, short course keelboat racing. Racers are welcome to helm their own boat, or have one of many experienced Courageous instructors take the lead around the buoys. At sunset we return to the dock and gather under the tent for catered food and drink and some of the best views in Boston. It makes Monday evening feel like Saturday night.


5. Fidelity

Your Impact

Courageous Sailing serves 1,000 children each year, most of whom would not otherwise have the opportunity to learn to sail or experience the ocean.

Our youth programs draw upon the rich natural and human history of Boston's waters. We seek to teach Boston’s youngest generation about the importance of protecting these invaluable resources; the possibility of careers in maritime, scientific and educational fields; and their ability to learn from and enjoy this city’s natural beauty to the fullest extent regardless of their socioeconomic status. For our students, our sailboats also represent a unique and powerful “classroom” that inspires the imagination, encourages personal growth, bestows positive life skills, and provides a social network from which students may draw energy and support for the rest of their lives.

Join the fun

Start the season off with your company team, enjoy waterfront access for 16 more weeks.

Each team competes with their company name and logo proudly emblazoned on their boat's jib sail, which remains on the boat through the entire season. And all participants enjoy a Courageous corporate membership, which makes it easy to keep sailing on Boston Harbor all summer long. Use your company’s challenge boat as a weekly perk for employees, or commit a dedicated team to the cause and try to win it all. Either way it’s sure to be a fulfilling way to spend a Monday evening while supporting the next generation of Boston’s youth sailors.



Past Participants

AlphaGraphics Amgen Anchor Capital
Arnold World Wide Atlas Venture Atwood group
Bank of America Merril Lynch BCG Bingham Dana
BNY Mellon Bookbuilders of Boston Bzz Agent
Cabot Caturano & Company Cox Engineering
CRP Delta Dental Detwiler / Fenton
Deutsche Bank E A P D Law Eastern Bank
Eastern Yacht Sales Eaton Vance Edwards Wildman Palmer LLP
Falcon Investments Fidelity Finnegan
First Marblehead Flagship Ventures Foley Hoag
Forrester Grubb & Ellis GVA Williams
Hylas Yachts Mc Gladery McKinsey
Mellon Capital Merrill Lynch MorganStanley
My Marketing Manager Nixon Peabody Northern Trust
Northfield Information Services Novell Old Mutual
Patriot Energy Group Peabody and Arnold Pembroke
Pomeroy & Co. PWC Reimer&Braunstein
Roux Sail Magazine Sail Time
Silvania Skinner Soveriegn Bank
State Street State Street Corporation Summer Associates
Sylvania The Boston Company The Stevens Group
Vitale Wachovia Securities Weeden & Co
Wells Fargo Wells Fargo Advisors Windhaven
Winward Investment   WJ Lynch
Xenon   Zoom Info