Work for Courageous

At Courageous we are committed to making the highest quality sailing education accessible to the community. We rely on instructors and staff members who are both great sailors and great teachers, super dedicated and hardworking, able to handle any number of unexpected surprises the day throws their way, and enjoy working in outdoors (most of the time). Even on the most challenging days, we still think this is a great place to work because of the role we play in the community, the opportunities we offer to kids and adults, and of course the best views of Boston from land or sea.

Current openings are listed to the left. See which one works for you. We look forward to seeing you down on the Pier.


  • 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



Courageous Mainsail Partners


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