• Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • 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 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
  • 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 natual energy sources. For the past several years, our youngsters have been learning about marine biology and ocean cleanup through award winning partner programs. Read More

Adult Program

Charlestown Adaptive Sailing Day - Sunday, September 7th


Presented by the Charlestown Waterfront Coalition, Courageous Sailing, and Piers Park Sailing Center.

Date & Time: Sunday, Sept. 7 - 12:00 pm to 3:30 pm.
Location: Breezeway of the Harborview building, next to Spaulding Rehab Hospital, at the base of 16th Street in Charlestown. View a Map

Each year in July and September, Courageous organizes and runs Charlestown Adaptive Sailing Day in cooperation with the Charlestown Waterfront Coalition and Piers Park Sailing Center. Adaptive Sailing Days are an opportunity for adults and kids with any sort of disability to come out for a free one-hour sail with an instructor from Courageous Sailing or Piers Park Sailing Center. A hoyer lift and physically adaptive boats are available for participants who use wheelchairs.  Families and friends are welcome, and lunch and bottled water are provided.

In the years that we’ve been hosting this event, it has proven to be an incredible experience for instructors, participants, and family members alike.  In the words of one mom affiliated with Special Townies, a Charlestown grassroots organization serving children with autism or special needs and their families, being on the water is “just about heaven.” Another mother noted that her son would happily sail all day if given the chance. Clients of Spaulding Rehabilitation Center have enjoyed the chance to get out on the water, too. Every year, more people become part of the community that participates in Adaptive Sailing Day year after year.

Please join us for a fun afternoon of sailing and good company! Click here to sign up.

For more information about Special Townies, check out their Facebook Page 

SailBlind Program

SailBlind, run at Courageous by the Carroll Center for the Blind since the late 1980’s, provides blind and visually impaired people with the opportunity to learn the art and science of sailing. Whether beginner sailors or veteran racers, blind adults and children can have fun and improve their skills using adaptive methods developed by the program, with the help of sighted sailors who volunteer as sailing guides. Participants in the Recreational Sailing program sail Rhodes 19s on Saturdays, and those interested in racing progress to the Step program in a J24, generously donated to Courageous by SailBlind for shared use. The Racing program practices on Wednesdays, and includes some world class racers--two SailBlind boats competed in in the Blind Sailing World Championships in Japan in 2013, with Matt Chao and his team coming in 3rd!

For more information about joining the SailBlind program as a sailor or sighted guide, please visit: www.carroll.org/services/recreation/sailblindYou can also learn more about the competitive world of blind racing through the documentary Sense the Wind, featuring some of our SailBlind sailors, at: www.sensethewind.com.


SailBlind's involvement with Courageous Sailing Center (then Pleasure Bay) began in the late 1970's and early 1980's.  At that time, we weren't even called Sailblind, and Courageous Sailing Center had yet to develop with the docking of the 12-meter namesake at the present site.

- Matthew Chao. Read his full story here.


Special Olympics of Massachusetts (SOMA) Sailing ProgramAdaptiveSOMA

The sailing teams of Special Olympics Massachusetts (SOMA) have been guests of Courageous Sailing since the early 1990s. SOMA begins weekly Wednesday practices shortly after Courageous opens for the season in May, using the Rhodes 19 fleet. Sailing is a “Unified Sport” in Special Olympics, meaning there are generally two athletes with intellectual disabilities as well as two coaches, called Unified partners, in each crew.

By late June each year, some fifteen or more teams from various parts of the state have honed their sailing and racing skills to compete in the Special Olympics Massachusetts Summer Games at MIT. Special Olympics sailors continue to practice at Courageous through September in preparation for the multi-state Rhode Island Special Olympics Invitational Regatta held at the Naval War College in Newport. Massachusetts sailors have won the gold in the top division most years.  

The Special Olympics sailors progress from Level 1, where a partner skippers the boat over half the time and athletes work the sails, to Level 3, there are three athletes who race the boat and one Unified partner who may only advise on tactics and strategy. Many of the SOMA athletes who train here have progressed from their first sail ever to being competent and confident crew members and competitive skippers. SOMA sailors are excited about how self confident their new skills make them feel, and how much they enjoy sailing and the social aspects of participating in the program.

For more information, visit www.specialolympicsma.org.

2014 Holiday-deal-header


Give the gift of sailing this holiday season! 

Looking for the perfect present for an experienced sailor? Want to give someone who’s never sailed before the chance to try something new? Courageous Sailing has lessons and memberships to fill every stocking...and to treat yourself! Even better, your gift will also help Courageous provide free and low-cost sailing opportunities for Boston kids.

Take advantage of our lowest prices of the season!


Frostbiting Week 4: There is always a lot to learn.
Hello Frostbiters, I trust that everyone had a great weekend and Nate ran things well in my absence. Before this week's guest blog by Mark, I have two announcements to share. We have two special events this upcoming Saturday, Rules Clinic, at Seaport School, this Saturday, December 20, 9:30-11am...
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Week 3 Recap: Overtaking at the Windward Mark
 I hope you are all staying warm and dry today. It is one of those days that you don't have to walk far before you look like you've fallen off the dock or been swept overboard. The good news is that this weekend should be warm (high of 45) and dry, with NW winds around 10 knots. I am taking a...
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Frostbing Week Two- Starts Are Hard
Barge- Move forcefully or roughly. Push, Shove, Force. "We can't just barge into a private garden party." or "Barging in at the start line causes havoc and makes Courageous staff anxious and competitors angry." Yes, this week's recap is about starts, and in particular, barging. Which there was a ...
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Week 1 Brings Great Weather, Great Racing
Current was coming straight down the course all day, making starts difficult at first. As the current slacked, the fleet was still pushing hard and we had several boats OCS, but no general recals occured.  In Race 1, the boats starting pin got over into a nice lefty shift, and were able to t...
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Welcome to the 2014-2015 Frostbiting Fleet!
Our first day is in just two weeks (November 15), so what should you be expecting? The best racing in Boston, with 25 boats on the line Newly re-painted and buffed R19s Evenly tuned boats (so no adjusted rigging!) Experienced support boat and RC staff A great group of highly skilled and c...
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