At Courageous Sailing, youth experience sailing as a platform to develop leadership skills, gain confidence, and experience hands-on environmental science. Even our newest sailors enjoy the thrills of skippering a boat, going fishing off our docks, and making new friends, the first steps on their journey to becoming integral members of the Courageous Sailing community.  Our 5-Step Summer Sailing School curriculum provides a framework for learning and growing through increasing independence, responsibility, and achievement. Read the Frequently Asked Questions for more information about Courageous Summer Youth Programs.

We’re gearing up for another awesome summer of sailing at both our Charlestown and Jamaica Pond locations! Our 2016 programs will run between Tuesday, July 5 and Friday, August 12.  The 2016 Summer Youth Program Lottery is now closed.

For information on the 2016 lottery registration, fees & scholarship eligibility, and step program registration, click here.

  • Beginner/Intermediate Rhodes 19

    For great informal racing on Boston Harbor, Thursday nights at Courageous is the place to be. Racing is a great way to sharpen your sailing skills…plus it’s fun! Read More
  • Advanced Rhodes Racing

    This competitive fleet attracts our top Frostbiters, as well as elite racers from various area fleets. Extensive racing experience and an in-depth knowledge of the racing rules are required to skipper; anybody is welcome to crew. Season prizes will be awarded. Read More
  • Laser

    A popular boat at every club around the world and Courageous has a fleet of 12 new boats with upgraded lines packages and rig options (Full, Radial, and 4.7) for each hull. We race Lasers on Tuesday nights in the spring and summer. Those wishing to store their own boat here at Courageous are encouraged, and even recieve a discount on the racing series. Read More
  • Frostbiting

    For the hard-core racer inside you that scoffs at some ice and snow. Despite taking place in the middle of a New England winter, this is our most popular racing series. Every Saturday from mid November through early April 24 Rhodes 19's can be seen racing in the best wind of the year on Boston Harbor. Read More
  • High School

    Boston Public High Schools and Boston Latin practice and race in our fleet of Club 420's in the spring and fall. Read More
  • PHRF

    Qualified cruising members are welcome to use our new CS30 for Wednesday PHRF racing, run by Constitution Yacht Club. Sportboat members are welcome to use one of our new J80s as well, subject to availability and skipper qualifications. Read More



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