Monday, 09 December 2013 16:47

Quote 2

"… relax and stop thinking about problems.”

Monday, 09 December 2013 16:44

Quote 1

"…try and conquer new things.”

Saturday, 30 November 2013 13:18

Annual Appeal | From the Executive Director

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
Monday, 25 November 2013 09:14

Damage Waiver

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.

Monday, 25 November 2013 09:14

Guest Pass

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.

Monday, 25 November 2013 09:12


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

Monday, 25 November 2013 09:10

Corporate Membership

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

Monday, 25 November 2013 09:10

J/22 Upgrade

The J/22 Upgrade gives you access to our fleet of nine J/22s, in addition to the Rhodes 19s, for just $100 more. While we all love the Rhodes 19, there comes a time when you want to sail in a higher gear. The J/22 is a fast and highly responsive keelboat, built for speed and performance.  You must pass an on-the-water J/22 checkout in order to sail them.

Monday, 25 November 2013 09:09

One Day

Regular Price: $95 + a one-time $50 checkout fee

Our One-Day membership option, similar to a boat rental, is perfect for experienced sailors who are looking for a little time on the water without a longer commitment. In order to take out one of our Rhodes 19s or J22s, we'll need to schedule a quick on-the-water checkout (including a crew overboard recovery drill and docking under sail) with one of our instructors, which you may do in advance or on the day you go sailing. A One-Day membership gives you access to Boston's inner harbor, and can last for a few hours or the whole day--it's up to you!

If you'd like to purchase a One-Day Membership, email to schedule your checkout and reserve a boat. 

Monday, 25 November 2013 09:09

One Month

Regular Price: $300

One-Month memberships make sense if you’ll be away for much of the season, or aren’t sure you want to commit to a full membership. Choose any 30-day period and sail all you want!

Purchase your membership now by clicking on the Purchase Memberships tab to the left!