Sailing in Boston Harbor in the evening

Create an Event


From the picturesque small boats on the Charles to the big boat racers on the Harbor, from the the visiting historic tall ships to the cutting-edge round-the-world Volvo raceboats, Boston is a sailor's city. There is simply no better way to experience its distinctive urban skyline than from the water.

Just next door to the living history of the USS Constitution in the Charlestown Navy Yard, Courageous Sailing has been teaching Bostonians to sail since 1987. Named after the famous America's Cup 12-meter yacht, Courageous was founded to make sailing on Boston Harbor accessible to all. As a US Sailing school with expert instructors and a large fleet of fun, safe, easy-to-handle keelboats, Courageous memberships and courses are some of the best, most affordable anywhere. And Courageous program revenue goes to support its youth program, which remains entirely free to kids in need.

crossing boats

With its unparalleled views and convenient location just steps from nearby Tavern on the Water, Courageous is the perfect venue for group events, large or small. BoatWorks and RaceWorks programs out of Courageous can be booked for as few as 12 and as many as 60 people.

GEL’s BoatWorks and RaceWorks experiences can be conducted on nimble Rhodes 19's or the slightly larger J22’s.

Looking for lower intensity or to accommodate a group of 4-12? Ask about Charting Change programs aboard one of Courgeous Sailing's racer cruisers.

Boston Weather

Weather courtesy of Weather Underground
Data provided by Weather Underground

Boats Available

  • Rhodes 19's
  • J22's
  • Seafarer 30
  • Erickson 28
  • Mirage 338


  • J 22 or Rhodes 19 BoatWorks Events, up to 60 people.
  • Seafarer or Erickson Programs, up to 6 participants per yacht.
  • Custom RaceWorks Programs can occasionally be structured for groups larger than 60.

"I didn't realize how challenging, inspiring and just plain fun our time on the water would be. This ranks as the best leadership training exercise we've done by far."


"The parallels between what goes on on land — i.e., our working environment — and what went on on the water were uncanny."

Ernst & Young

"Merging two large, geographically dispersed organizations offered some unique challenges. Jay and GEL were tremendous."

Partner, Booz Allen Hamilton

"Jay and his team put together one of the most effective and enjoyable days of team-building activity that it has ever been my pleasure to participate in (and I've been in far too many)."

IFC/World Bank

"Most of our leadership program participants have never sailed before. Trepidation? Sometimes. Positive feedback? Always."

The Symphony Group