Every year, Courageous serves over 1,000 kids from Boston, hosts events and regattas, and provides instruction and waterfront access to hundreds of individuals, families, and corporations.
Spend the best summer of your life teaching sailing, science, and life skills at Courageous!
Get a taste of sailing or enjoy a leisurely cruise around the harbor - the choice is yours!
Need to brush up on specific skills to pass a flag rating? Or maybe you need specific times outside our normal course schedule.
If you're just in town for a couple of days or thinking about becoming a member, a one day rental might be your best option.
Learn to sail in just two weekends, no previous experience required.
Become a member and sail our fleet from the Mystic River to Hull and everywhere in between.
Blind match racing is a growing part of sailing with fully visually impaired sailors competing.
Courageous helps provide access to the waterfront for Charlestown residents with special needs children.
Special Olympics of Massachusetts trains in our fleet of Rhodes 19's.
Every Monday evening in June, 25 teams from Boston area companies race in the Challenge to raise money for Courageous Youth Programs.
Small to large team building exercises, daytime or evening events, 1,000 person capacity tent.
There are no upcoming events.
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Once you start sailing the bigger boats, it’s hard to stop! And there’s always more to learn. Our Bareboat Cruising course is the next step. It picks up where Basic Cruising leaves off and covers topics such as navigation, anchoring, and heavy weather sailing in much greater detail. You’ll learn the things you need to know when chartering a sailboat: controlling the boat under power with confidence; big boat docking techniques; provisioning; visiting the fuel and pump-out dock; VHF communication; and more. We will also take you through a tour of all the important boat systems, pulling up cushions and floorboards so you know exactly where everything is, what it does, and what to do (or who to call!) when it doesn’t work. This course typically includes 3 days of sailing, two overnights at anchor or moored, and additional prep and debrief time. Maximum of 4 students.
2021 Update- Posted November 2020
Due to Covid 19, we were unable to fulfill a number of of our courses from the 2020 season and will be working to execute on those courses before posting new ones. If you would like to join our Waitlist please sign up here. Any contacts on our waitlist will be the first contacted when we post new courses and/or open enrollment for the 2021 season.
Many course participants choose to test for their US SAILING Bareboat Cruising certification, which signifies that you have sufficient skills and knowledge to safely and confidently skipper an auxiliary powered cruising sailboat between 30’ and 45’ in length, in winds above 15 knots, within sight of land during daylight hours. This certification is widely respected and accepted by many sailboat charter companies in the US and other parts of the world. Most Bareboat graduates are also qualified for a Courageous cruising membership.
Passing this course along with the associated prerequisites qualifies the student to apply for their International Proficiency Certificate. This is needed if they wish to bareboat cruise in the European Union (EU). For more information regarding the IPC please contact email@example.com
You can see the whole US Sailing Bareboat Cruising curriculum online here.
Cancellation and Refund Policy: Please note that in an effort to keep our courses and memberships as affordable as possible, we must limit changes in schedule and membership. Because staff and instructors are hired and scheduled in advance, Courageous memberships, lessons, and/or other program fees are not refundable for any reason, including cancellation due to weather, or the participant’s inability to utilize the membership, lesson, or program. That said, we do understand that sometimes life gets in the way of sailing plans and, if necessary, we will work with you to reschedule for a later date. We cannot reschedule lessons within two weeks of their start date unless we are able to fill the spot with another student. All rescheduled lessons purchased before September 1 must be completed before the end of the season for which they were purchased; if purchased between September 1 and October 31, rescheduled lessons must be completed before June 30 of the following year.
This year, our team thoughtfully constructed a program that would recreate in the virtual world the community that makes being on the pier so special. Our top priority was to support our kids emotionally and help them address the feelings of isolation, anxiety, and stress that many were experiencing. Our strategy:
“I think every year with kids at Courageous you see relationships form. I think whether online or in person, I still had those relationships form with students and coworkers… One thing Courageous does well is unity. I have always found myself making new friends, connecting with old ones, and becoming friends with my instructor. Courageous to me is one big family and I think everyone is always there to support you.”—Jean, Swim Sail Science instructor and former Courageous kid
After our kids’ tough spring of remote learning in school, we knew that it would be critical to make the online Courageous Sailing experience hands-on and interesting, especially because many of our students—especially those already disproportionately affected by the upheaval of the pandemic—had lost so much ground academically. We needed to make learning fun! Our strategy:
“I was SO impressed at the job your team did. On the first day I walked by my Step 5 (somewhat sullen, quarantined) teenager hearing him laughing and happily engaging with his group. Then hearing what they were doing everyday was so amazing. Highlights I heard about (or watched): the sailing regatta app (so cool!); The underwater view of the sea under the dock; the interview with the Commander of the Constitution (that was really amazing)! I commented to my husband that the Courageous Team should be coaching the schools on how to run Zoom meetings.”—Kristin, Courageous parent
Youth are living in a world that can feel frightening, hostile, and unjust—a place where it’s difficult to feel safe, set worry aside, and just be a kid. Whether on Zoom or on the water, Courageous made sure that our students had plenty of opportunities for fun.Our strategy:
“I could have fun at home as much as outside.”—Ryhan, Courageous student“My favorite memory from Courageous is hanging out with instructors and friends and having fun with them!”—Zhencong, Courageous student