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 around 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 30 feet, including three J/24s, an O’Day 240, a Tartan 27, an Erikson 28, and a Seafarer 30. We offer three classes of cruising memberships: our entry level option (Cruising C) provides access to the J24s and O’Day 25 for day trips, the next level up (Cruising B) enables overnights for the same fleet, and our Cruising A option provides access to the full fleet for day trips and overnights. Cruising membership also includes access to our fleet of twenty five Rhodes 19s and nine J/22s.

We carefully limit our available cruising memberships to ensure everyone has plenty of access, so sign up soon! Starting Monday, December 2, we will make six 2014 memberships available at each of the three Cruising membership levels--if you are sure you want in, please email or call us ASAP and we will put you on the waitlist. If you’re interested in a cruising membership, please email Jake Denney, our Adult Program Director, at

This membership works like a Full membership for your entire staff. Any qualified skipper on your company's employee list or holding a company ID can sail. Courageous offers one, two, or three boat Corporate membership options, depending on how many boats employees might want to use at one time. Have a client who’d enjoy a tour of the harbor under sail? We make it easy, with guest passes included in all corporate memberships. 

To learn more please contact Jake Denney, our Adult Program Director, at

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.

Our One-Day membership option is perfect for out-of-town visitors who are experienced sailors looking for a little time on the water. It’s also a great option for anyone who’s not sure which membership is right for them and wants to come down and check us out!

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!

Price: $395

Our weekday memberships are terrific value! If you’ve got the freedom to sail during the week and take advantage of the late summer sunsets, a Weekday membership may be your best bet, and they are very easy on the budget.

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

Price: $495

The Weekend membership makes a lot of sense for anyone who knows that weekdays just won’t work.  Come out on Saturdays and Sundays all season long!

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

Price: $745

A Family membership is like 3 Full memberships for just $100 more.  Up to 3 skippers in a family can sail under a Family membership, either together or separately. This provides the same access to our great fleet of Rhodes 19s, but for the whole family!

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

Price: $645

Our Full membership gives you access to our whole Rhodes 19 fleet (25 boats!), 7 days a week, May 1st through October 31st (or for one calendar year if purchased after May 1st).  It is by far the best value on the harbor.  For an additional $100, get the J/22 upgrade and use our J/22 fleet as well.  Don’t forget a Guest Pass so that you can take your friends and family sailing!

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

Wednesday, 11 September 2013 10:42

Course Purchase Complete


Congratulations on purchasing a Learn to Sail course at Courageous.

Not only will you be learning a life-long skill that you can enjoy with friends and family, your purchase of this course will support Courageous' vision to remove barriers to access for all Boston youth, the public and people with physical and intellectual challenges.


Please contact the Adult Program to schedule your course.

(617) 242-3821 x17


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