Know somebody who’s ready to take their sailing skills up a notch, or who is looking for a way to get out on the water without the hassle and expense of boat ownership? Courageous has a variety of courses, ranging from a 12-hour beginner course to Advanced Keelboat to Bareboat Cruising, to challenge sailors of any level. Our different memberships offer access to the boats in our fleet, so that old salts and graduates of our courses can sail Boston Harbor in style.
In just 2 weekends, our Basic Keelboat Complete course will give a total sailing novice the opportunity to learn all they need to sail on their own, for just $440. This hands-on 24-hour US Sailing course is taught by one of our expert instructors in a 19 foot keelboat with up to 3 students. Combine the course with a 30% off Full or Family membership so that the newly minted skipper will be able to sail at Courageous all season long.
If you know someone who would love to give sailing a try, this is a gift they’ll love! This two-hour sail is an opportunity for up to 3 or 4 people to experience the views from Boston Harbor, learn some sailing skills, or just sit back and enjoy the ride on a comfortable Rhodes 19 keelboat. An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise.
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), J/22s (faster, more responsive keelboats), 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.
To book your charter, please email email@example.com, or call us at 617 242 3821.
Courageous can also accommodate private groups requiring 2 or more boats. See our Corporate Functions page for more information.
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.
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, 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!
Weekend & Holiday pricing:
Rhodes 19: $95
Rhodes 19: $65
One-time checkout fee applies to all one-day memberships ($30 for Rhodes 19 + J/22, $50 for J/24). Checkout fee is waived if you complete your checkout in under 30 minutes on the water.
To purchase a One-Day Membership, select the appropriate option from the dropdown menus on our membership page. Weekend rates apply on Memorial Day, July 4th, and Labor Day. Please email firstname.lastname@example.org to schedule your checkout and reserve a boat.