Adult & Family Sailing

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

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.

This is the best way to learn the basics and then sail at Courageous as a member once you’re ready to sail on your own. All Learn to Sail courses are taught in Rhodes 19's and are suitable for most ages and abilities. The goal of the class is to get you on the water with a red flag rating to practice the skills you have learned.

The next step for sailors looking to increase their skills, Courageous offers advanced keelboat and cruising courses. These course goes cover in-depth sail trim, advanced theory, docking and piloting on a larger and faster vessels.

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.

The Rhodes 19 is backbone of the Courageous fleet with 27 Stewart made keelboats and counting. Stable and easy to handle, they offer a fun, comfortable sailing experience for sailors of all calibers, from novices to seasoned one-design racers.

The J22 is a popular next-step for our members looking for a little more elbow room and offers 7 day/week access all season long. Membership includes access to our R19 fleet ensuring you'll never be left without a way to get out on the water.