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.

Just Getting Started?

You’re in the right place! We’ll be happy to work with you to set you up with the private lessons or group class that fits your schedule, learning style, challenges, and goals. Most beginners choose to combine Basic Keelboat Complete (a two-weekend course) with a Full membership, so that you can start by learning the basics, and then sail at Courageous as a member once you’re ready to sail on your own.



Become a full time sailor without owning a boat. Pick up a full membership and sail on Boston Harbor from May through October.

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.