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?

Most beginners choose to combine Learn to Sail (a two-weekend course) with a Full membership, so they can learn the basics and then sailing at Courageous on their own as a member.

Get the Learn to Sail Package

Sailing 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. Our Learn to Sail courses are extremely hands-on and have a 1:3 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.

2 Hour Sails

A great way to get introduced to sailing. Give as a gift or purchase one for yourself!.

Buy a 2 Hour Sail


Become a full time sailor without owning a boat. Signup for a Courageous membership and sail one of our boats on Boston Harbor or to the islands from May through October.

Rhodes 19 Membership

The year-long individual membership is our most popular option, yet with a 27 boat fleet there is always opportunity to get on the water.

Join Today