Summer vacation doesn’t need to be over!

Fall is the perfect time to experience Boston Harbor, and Courageous Sailing is offering special deals for Charlestown residents.

  • Basic Keelboat Complete  Learn to sail in just 2 weekends, then sail free through October 31!

  • 2017 memberships Includes free fall membership through October 31.

  • Combine the two to save even more, and get a free refresher lesson in the spring!

  • Fall 2-hour sail for just $95, 50% off! Want to give sailing a try before you sign up? Take a 2-hour lesson or cruise with one of Courageous’s fantastic instructors for just $95.

Purchase Courses
Purchase Memberships
Courageous's sailing season runs from May 1 to October 31. Basic Keelboat Complete course must be taken over two consecutive weekends, Saturday and Sunday from 10-4:30 each day, and completed before October 31. At the conclusion of your course, you'll need to demonstrate competency and knowledge of sailing basics in order to sail as a member. Courageous membership includes access to our fleet of 27 Rhodes 19 keelboats, plus free or discounted member activities like cookouts, camping trips, moonlight sails, racing, and more. Free refresher lesson (2 hours) must be taken in May or June 2017. Memberships purchased with Free Fall expire October 31, 2017.

Adult Program

Whether you’re an old salt or you’ve never been on a boat before, Courageous is the place for you!

At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor.  Maybe you’re looking to learn the basics or explore the Harbor Islands, or you want a convenient way to take your family and friends out sailing without the hassle and expense of boat ownership.  Or perhaps you’re a hardcore racer or a veteran cruiser.  No matter what your style or skill level, you’ll find that there’s a spot for you in the Courageous community. 

Adult Program Courses

Whether it’s your first time on a boat or you have years of experience under your belt, when it comes to sailing there’s always more to learn.  We offer a wide range of courses, led by expert US Sailing certified instructors.  Our classes are extremely hands-on and are kept small (usually no more than three students in the boat with an instructor) for a highly individualized learning experience.  While our group classes are geared towards adults (18+), we are more than happy to set up private lessons for families or individuals of any age and experience level.   You do not need to be a Courageous member to take a course.


Learn more about courses



A Courageous membership means that you can take one of our boats out for a sail on Boston Harbor whenever you’d like.  There are many membership options for individuals and families, including monthly, weekend, weekday, and full annual memberships.  Different memberships offer access to different types of boats in our fleet, ranging from daily use of our Rhodes 19s to overnight trips on our larger cruising boats.   Membership also includes much more: barbeques, racing, fireworks-watching parties, moonlight sails, Harbor Island camping trips, and discounts on courses.  As a Courageous member, you’ll be a part of an enthusiastic, inclusive community of sailors...and you’ll be helping Courageous provide free and low-cost sailing opportunities for Boston kids.

Learn more about membership

Contact the Adult Program


Bryan Lee

Adult Program Director
617-242-3821 x14



Courageous Mainsail Partners


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