Adult Memberships (8)

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

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. 

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!

Price: $445

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: $545

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!

Regular Price: $845

A Family membership is like three Individual full memberships for just $100 more than a single membership. If there are 2 or 3 adults in your family who would like to sail -- but you don't always plan to sail together -- a Family membership is the way to go. This provides the same access to our great fleet of Rhodes 19s, but for up to 3 skippers. Don't forget to add on a Guest Pass, so that all 3 members can take out friends and family!

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

Individual Full Membership

Free membership through October 31, 2015 with the purchase of a 2016 membership!

Regular Price: $695 

Our individual Full membership gives you access to our whole Rhodes 19 fleet (27 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 $150, get the J22 upgrade and use our more high performance J22 fleet as well. Don't forget a Guest Pass so that you can take your friends and family sailing!

Members must pass an on-the-water checkout and written test in order to sail a Courageous boat without an instructor; please see our Flag Ratings section for more information. Our sailing area extends out around the Harbor Islands for qualified members. Courageous is open noon - sunset on weekdays and 10 - sunset on weekends and holidays, May 1 through October 31. Boat availability is usually plentiful (with the exception of before 3:30 on weekdays during our 6-week summer Youth Program), but is not guaranteed.

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



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