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

Intermediate and Advanced Sailing

Once you know the basics, you may be looking to increase your skills or learn about larger vessels. Courageous offers courses than can satisfy a whole range of interests on an easy to sail and adaptable J80. Whether you want to take a few more friends out to the Harbor Islands or you want to finally give the asymmetrical spinnaker a try, our courses will provide all the tools and confidence you might need to achieve those sailing goals.

Cruising Courses & Certification

Everything you need to get started on cruising! Basic Cruising will teach you everything you need to know to start cruising Boston Harbor and the Boston Harbor Islands. All courses are taught on one of our five cruisers, including our First Mate course, in which our students learn the skills to be a competent and confident crew. Start with the basics and then work your way up to becoming Bareboat certified and ready to take on a week in a chartered cruising boat down south next winter.


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

J80 Fleet

The J80 is a versatile option for those sailors seeking a larger vessel that can race as well as go for a leisurely cruise to the harbor islands. This fleet 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.

Cruising Fleet

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.