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

About Courageous


Our Mission

Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth and leadership.

Our Vision

Courageous Sailing is a community that embraces sailing as a platform for life-long learning, personal growth and leadership; a center of sailing excellence committed to removing barriers to access for all Boston youth, the public and people with physical and intellectual challenges.


Courageous Sailing was established in 1987 as a 501(c)(3) by the late South Boston sailing enthusiast Harry McDonough. It was Harry’s dream to use sailing to build character and camaraderie among Boston children from all economic and ethnic backgrounds.  For 25 years, we have continued to grow and deliver our mission to transform children’s lives through sailing programs that inspire learning, personal growth and leadership.  In Harry’s words, “Every child's perspective is improved 50-yards off-shore.”

Courageous is now a nationally recognized year-round educational center for community sailing and youth development.  Courageous offers Boston-area youth free and low-cost out-of-school-time programs in sailing, environmental education, job skills development, and leadership training. In 2011 we were honored to be named one of the top 10 community sailing programs nationwide by both US Sailing and Sail Magazine.

How Courageous Got Its Name

The America's Cup 12 meter "Courageous" once lived at Pier 4 in the Navy Yard. This two-time America's Cup winner lent its name to Courageous Sailing in the late 1980s. The boat now resides at the Museum of Yachting in Newport, Rhode Island, where it has been restored and is still being raced.

Our Partners in Community Service

Courageous is proud to partner with many like-minded nonprofit organizations.  During our longstanding relationship with Special Olympics of Massachusetts, Courageous has hosted the Special Olympics Summer Games, and continues to be a host training venue for Special Olympics athletes two days each week.  We have another close partnership with The Carroll Center for the Blind, whose pioneering Sail Blind program has called Courageous a home base for two decades.  With the Carrol Center, Courageous has been host to national blind sailing regattas, the annual Harry McDonough Regatta for the Blind, and weekly Sail Blind racing and recreational practice sessions.  Courageous is also home base for the Big Sisters Association of Greater Boston's annual Adventure Sail program for inner-city girls, an event that has drawn hundreds of women and girls into the sport of sailing.  In recent years we have been developing new and exciting relationships with Boston Family Boatbuilding, Boston Afterschool and Beyond, and the Boston Public Schools.

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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

Register one boat, or two!

We've made it even easier for you to bring two teams (and help send more kids out on the water this summer!)

  • Sponsor six to ten children for the week-long Youth Program Sailing 101 course
  • 5 nights of racing on Boston Harbor - May 23; June 6; June 8; June 13; June 20; June 27
  • Company logo on the jib sail for the 2016 season
  • 20% discount on Learn to Sail Courses
  • Level 1 Corporate Membership from May 1st through October 31st


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Call or email Dave DiLorenzo to register your company for the Corporate Challenge

617 242 3821 ext.10