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

Evening Racing

With 6 total nights of racing in 2014, 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.



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5. Fidelity

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.

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.


Register one boat, or two!
This year we've added an extra night of racing, plus 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
  • 6 nights of racing on Boston Harbor

    May 19; June 2; June 9; June 16; June 23; June 30

  • Company logo on the jib sail for the 2014 season
  • 20% discount on Learn to Sail Courses
  • Level 1 Corporate Membership

    Send your staff sailing! All your employees can enjoy the advantages of a Courageous membership, enabling sailing all season on Boston Harbor from May 1st to October 31st (Limit one reservation at a time)


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

617 242 3821 ext.10


challenge event-sponsors


Every year the Corporate Challenge is a success is due in large part because of these companies that help make it happen

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