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

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.

If fast, friendly, easy to sail boats and Harbor Island cruising are calling your name, this is the membership for you! The Mid-Fleet Cruising membership gives you access to our three J80s and two Pearson 26s.

For some of us, it’s all about the big boats and thoughts of sailing around the world. Our cruising fleet won’t take you quite that far, but it will take you around Boston Harbor and then some. Whether you want to invite friends and family for trips around the Harbor Islands, anchor for a picnic lunch, spend a night moored or at anchor under the stars, or practice your big boat skills in preparation for a bareboat trip in the Caribbean, our cruising membership has you covered.