Monday, 09 December 2013 16:53

Quote 3

Written by

“… work together better with other kids.”

Monday, 09 December 2013 16:47

Quote 2

Written by

"… relax and stop thinking about problems.”

Monday, 09 December 2013 16:44

Quote 1

Written by

"…try and conquer new things.”

Age Rising 3rd and 4th graders
Swim Requirement None. Weak and non-swimmers welcome. Swimming classes are provided by the Charlestown YMCA and the Curtis Hall Community Center (Jamaica Plain).
Experience Requiment No experience necessary. New sailors welcome.
Limits One 5-week session per child per summer. Closed enrollment. Must be referred by a partnering Boston Public School.
Daily Schedule

8:30 AM - 3:30 PM*, Monday - Friday

*drop off begins at 8:00 AM at the Harvard-Kent School; 3:30 pick-up also from the Harvard-Kent; extended day option available

Dates Mon 07/06/15 - Fri 08/07/15 (tentative)
Locations Charlestown and Jamaica Pond (transportation may be available for both locations)
Cost $0
 To Register: To receive announcements about registering for the 2015 SSS program, complete this form.

Course Description:

(01/29/15 Note: At this time, program details have not been finalized. Thank you for your patience as we work to make the 2015 program possible!)

This five-week long program is a great way to introduce your child to Boston's waterways. The program is designed to build students' confidence around water, knowledge of water and boating safety, and appreciation of the natural environment.

As part of our Summer Sailing School, we operate two other summer programs: the Summer Learning Project (SLP) and SwimSailScience (SSS). Both programs specifically target Boston Public School students identified as being at risk for summer learning loss. The students in these programs receive transportation, two meals each day, and lessons in swimming, sailing, and science, all at no cost to their families. No prior sailing or swimming experience is necessary for students to attend. Unlike our "Step" programs, students must be referred by their schools in order to register. Past Boston Public School partners for the Summer Learning Project have included the Harvard-Kent, Warren-Prescott, Adams, Haley, and Young Achievers.

Note: Registration for the 2015 Summer Learning Project is not open to the general public. Registration for the 2015 Swim Sail Science program will be conducted at select Boston Publics Schools. Please return to this website in late February 2015 for more information on which schools we will be working with.

Check out video of the 2013 Summer Learning Project Program.

From the Executive Director

When I joined Courageous in the summer of 2007 as the youth program racing coach, my biggest challenge was our youngest racer, Emily. Full of promise but short on attention span, she seemed to specialize in undoing the best-laid lesson plans. Whether off collecting jellyfish during chalktalks, or jumping out of her boat during a race to go for an unannounced swim, she had a knack for doing things her own way. There was no arguing with the amount of fun she was having, but it was not exactly the kind of race training I had in mind.


That summer, and every summer since, Courageous provided Emily with opportunities to grow and develop her skills–and she did. In 2011 she graduated from our Instructor-in-Training program, and just completed her second year as a full-fledged instructor. This season, when one of our younger students was struggling with some difficult issues in her life, she turned to Emily.  It wasn't an easy situation, but Emily responded with sensitivity and maturity that made all the difference.


For me, seeing Emily grow through the Courageous program–becoming not just a great sailor but a role model, mentor, and teacher who is able to give back and make a difference in the lives of our youngest Courageous kids–is what it's all about. This fall, Emily just started her freshman year at URI, where she has–no surprise–joined the sailing team.


This summer was full of countless similar moments. There is a long, long list of Courageous kids– Maia, Matt, Adam, Colleen, Liz, Jack, Sara, Kayla, Alexis, Griffin, Morgan, Luke, Ian, Will, Mikaya, Kelsey, Amy, Anthony, Claire, Audrey, Leo, Kieran and so many more–who, in what feels like the blink of an eye, have become incredible leaders and role models.


This season we have so much to celebrate.  We were again a major partner for the award-winning Boston Summer Learning Project. We received our biggest grant ever from the Mabel Louise Riley Foundation, enabling us to dramatically improve our outreach to underserved communities and launch an exciting new program that combines swimming, sailing, and marine science classes for 60 rising fourth, fifth, and sixth grade students from the nearby Harvard-Kent school in Charlestown.


As I head into my seventh year at Courageous and my second year as director, I am moved beyond words by the accomplishments of the Courageous community over the past 26 years. One person at a time, one act of generosity at a time, we have built one of the country's leading organizations dedicated to using sailing as a platform for growth, learning, and empowerment. I hope you will join me in continuing to support the Courageous mission.


Thank you,
Dave DiLorenzo, Executive Director

Private Keelboat Charters

A private charter is a fun opportunity for a group of up to 3-5 people to get out on Boston Harbor in a sailboat, with no need to worry about planning a thing! Experience the fantastic views of the city from the water, learn some sailing skills or take the helm if you’d like, check out some Boston landmarks, or just sit back and enjoy the ride.  An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise for you.  We have a variety of boats available for charter, including Rhodes 19s (comfortable 19-foot keelboats that fit up to 3-4 people), J/22s (faster, more responsive keelboats that fit up to 4 people), and our cruising boats, which can fit 4-5 and are suitable for longer trips around the Harbor Islands.  Feel free to bring a picnic or snacks for the sail (note that alcohol isn’t permitted before or during sailing).  Life jackets are provided.  Minimum of 2 hours; price includes as many guests as can safely fit on the vessel. 

Courageous can also accomodate private groups requiring 2 or more boats. See our Corporate Functions page for more information. 

Rhodes 19: $95/ hr (Minimum of 2 hours per lesson; price includes up to 4 guests.)
J/22: $125/ hr (Minimum of 2 hours per lesson; price includes up to 5 guests.)
Cruising Boat: $150/ hr (Minimum of 2 hours per lesson; price includes up to 6 guests depending on vessel.)
Please contact us directly at 617.242.3821 to set up your private charter. 

Members who purchase the optional damage waiver are released from financial responsibility for physical damage to Courageous boats in their care and custody, so long as it is not caused by the Member's negligence or intentional conduct, violation of the Courageous Sailing Agreement & General Release and Membership Terms & Conditions, failure to stay clear of other boats and obstacles, or running aground.  No waiver of damage liability shall be effective until the damage waiver payment is received.  Please note that the damage waiver does not waive financial responsibility for damage or injury to other boats, property or people, towing services, or lost equipment.  Please read our Sailing Agreement & General Release and Membership Terms & Conditions to fully understand our policies.

For a one time fee of $50 per season, a guest pass allows you to take as many guests sailing with you as many times as you want throughout the season.  Generally, a Rhodes-19 or J/22 can fit one skipper and 3-4 guests safely at one time.

Regular Price: Daysailing 24: $1150. Cruising 24: $1300. Cruising 30: $1900. Cruising 34: $2200.

For some of us, it's all about the big boats, backup engines, and thoughts of sailing around the world. Our cruising fleet won't take you quite that far, but it will take you out of the harbor and then some. Whether you want to invite friends and family for trips around the Harbor Islands, anchor for a picnic lunch, spend a night moored or at anchor under the stars, or practice your big boat skills in preparation for a bareboat trip in the Caribbean, we've got a convenient cruising membership option for you.

The Courageous cruising fleet is growing and improving every year, with boats ranging from 24 to 34 feet, including three J24s, an O'Day 240, a Tartan 27 yawl, an Erikson 28, a CS 30, and a Pierson 34. We offer four classes of cruising memberships. Our Daysailing 24 entry level option provides access to the J24s and O'Day 240 for day trips. The next level up (Cruising 24) includes overnights on the same fleet. Cruising 30 members may take the 27-30 footers for day trips and overnights; Cruising 34 membership includes the Pierson 34 as well.

Cruising membership also includes access to our fleet of twenty seven Rhodes 19s and nine J22s. All cruising members will need to have a check-out and orientation for the boats they will be sailing; please see our Flag Ratings section, especially "Green Flag for Cruising Members," for more information.

We carefully limit our available cruising memberships to ensure that everyone has plenty of access. To learn more about pricing and availability, please email Jake Denney, our Adult Program Director, at

Talk about a fantastic company perk! Courageous makes it easy for you and your coworkers and employees to get out on the water. We offer two types of Corporate memberships to fit your needs:

Corporate Full Membership
Price: $1500 for one boat; $500 for each additional boat.

This membership works like an Individual Full membership, shared by your entire staff. Anyone on your company's employee list or holding a company ID can take out a boat, once they've earned a flag rating (see our Flag Ratings section for more information). This option works best if you've got employees who are already skilled sailors, so that they can take other staff and clients out sailing. Choose the one-boat, two-boat, or three-boat option, depending on how many boats your staff members might want to use at one time. A corporate guest pass is included, so that employees can take clients, friends, and family out for a sail. J22 upgrades may be purchased by individuals. On-the-water checkouts for the first 3 sailors who want to earn flag ratings are free; checkouts for additional sailors cost $50. All employees also enjoy the benefits of membership, including discounts of 10% off courses and 50% off private lessons.

Want to take it up a notch by adding the excitement of racing in a weekly June series? Check out our Corporate Challenge page for more information. A Corporate Full membership is included with participation in the Challenge.

Corporate Passbook
Price: $1150 for 10 passes; $1800 for 20 passes; $2350 for 30 passes

Don't have many experienced sailors on staff? No problem--Courageous does! A Corporate Passbook provides you with 10, 20, or 30 passes, each of which can be redeemed for a 2-hour sail for up to 4 people, with one of our expert instructors aboard. You may use up to 3 passes at a time, allowing up to 12 employees or clients to sail in three of our comfortable, stable Rhodes 19 keelboats. Each 2-hour sail can be a private lesson (beginner or more advanced), a relaxed cruise, or a bit of both. All passes must be used within one season. Please contact us at least a week in advance to schedule your 2-hour sails.

Please contact Jake Denney, Adult Program Director, to purchase Corporate memberships at