• 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
  • Support Courageous Kids

    As 2015 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
  • 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
  • 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.
Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
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Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
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More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
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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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Happy, Excited, and Free
Youth Program
For the past four years, I have had the privilege of working with students from Swim Sail Science, a program Courageous created in partnership with Boston Public Schools. The SSS program aims to serve students who are at risk of summer learning loss. These students continue their academic studies th...
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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



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