• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond


Friday, October 9: With winds expected to build to an average of 19 knots with gusts to 32, plan for restrictions for Red and Yellow Flag skippers and the possibility that Courageous will be closed for all sailing.          Please check back before heading over!
  • Work at Courageous

    The 2015 season is just around the corner, which means there is an opportunity for you to come spend your summer working at Courageous. You'll be outside and on the water with a great staff and sailors from age 8 and up. This could be the start of your lifelong passion for teaching sailing, educating, and organizing in your community. Read More
  • Leadership + Growth

    Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Read More
  • Environmentalism at Courageous

    Courageous is wind powered, but we do more than just use natural energy sources. For the past several years, our young sailors have been learning about marine biology and ocean cleanup from our own Environmental Educators and award-winning partners. Read More
  • Support Courageous Kids

    As 2014 draws to a close, Courageous is celebrating a successful year of teaching sailing and more to Boston kids, and looking ahead to next year. Please consider supporting Courageous in our mission to provide high-quality summer learning opportunities for the kids who need them most by making a tax-deductible donation to our Annual Appeal before December 31. Read More
  • Awareness Campaign

    See our new awareness campaign made by Hill Holliday and Courageous board member, Joe Berkeley. The campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids. Read More

Racing in our J/22 fleetMember Benefits & Events

Your membership at Courageous provides much more than simply the freedom to sail on Boston Harbor and the surrounding waters whenever you like during the regular season.  Members also enjoy affordable sailing clinics, member barbecues and parties, regattas, night sails, discounted full courses, deals on sailing gear, and much more.

Camping Trips
Camping trips are back in 2012!  Check back soon for dates and contact us to sign-up early.

From May through September, we race each night, Monday through Thursday.  For 2012, Mondays mean J/22 team racing, with a rotating schedule of fleet, team and match racing.  Tuesdays are our night for Advanced Rhodes 19 fleet racing, Wednesdays our J/22 skippers can try their luck against the big boats in PHRF racing, and Thursdays are our open Rhodes 19 fleet racing series, complete with chalk-talks, on the water coaching and post-race debriefs.  When the days get shorter in the fall, we'll switch from Thursday evenings to Saturday afternoons for our R-19 racing.

Feeling rusty?  Stop in on alternate Saturday and Sunday mornings from 10:30am - 1:30pm for three hours of group instruction (for just $25).

A great Courageous tradition. This season, every Thursday, after racing.  Or on other days, the grill is available to members, so help yourself and have a picnic on Pier 4!

Member Parties!
Every month. The views from Pier 4 make it a great place to spend an evening.  These are a great way to meet your fellow members, and make new friends to go sailing with.

New Sailor Nights
Every two weeks. Come down, meet other members, share what you know. Let's keep the community in community sailing!

New Racer Nights
Every two weeks. Come down, get paired up with experienced racers and find out what all the fuss is about on the race course.

Harbor Island Tows
Twice monthly, we cut out the commute for Harbor Island-bound members with Saturday morning tows.  Whether sailing alone or as a flotilla, we'll get you past the airport fast so you have more time to explore.  Skippers must be approved by Dave or Cha. 

Moonlight Sails
A full moon means night sailing! Meet at Courageous for a cook out on the pier, rig your running lights, and set off for a breathtaking sail under the skyline of Boston.  Boats are restricted to the inner harbor.

Discounts on Courses
Our courses are the best deal around. For 2011 we are offering a full selection of the courses you have been wanting and asking for, taught by the highest quality, US Sailing certified instructors. No matter where you are in your sailing career, there's always more to learn. Do yourself a favor this year and sign up early. Members get an extra 10% off our already great prices.

Great Deals on Sailing Gear
Check out our store, and don't hesitate to contact us directly to learn more!  Email lindsey@courageoussailing.org or call us at 617.242.3821.
Life as a Courageous Kid
Youth Program
My 18th birthday, this April, inspired me to do some serious thinking about what it means to be mature and how I define adulthood. At the same time that I was working through these big questions for myself, I became a member of the senior staff for the first time at Courageous. Although I ...
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Speaking my Language
Youth Program
This summer, I was a sailing instructor in Courageous' Swim Sail Science program (otherwise known as SSS). The SSS students are from various diverse backgrounds and live all over the city of Boston. With that being said, the kids represent several different ethnicities and do not always speak Englis...
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Experiencing the J/80s
Youth Program
This past spring, Courageous received a donation that allowed the purchase of two J/80s.  J/80s are 26-foot-long sloop-rigged sport boats, with a roller furling headsail and an asymmetrical spinnaker.  The intention is, assuming Courageous likes the J/80s and finds that they suit its needs...
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A Place for Growth
Youth Program
This summer, my second at Courageous, I had the opportunity to gain a greater understanding of the Youth Program as a whole. Previously while working with the Instructors in Training, I only had a narrow view of that one piece of Courageous. Returning to Courageous, I was excited to become a part of...
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How Blue Note came to Courageous
One of of my favorite stories of 2015 is the arrival of Blue Note.   A comfortable yet sprightly 30 footer in wonderful condition, Blue Note comes to us through the generosity of the family of Dr. Paul Blum, a remarkable scientist, Peace Corps volunteer, and Boston Harbor sailor.  Blue Not...
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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



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