Signup for a Courageous membership and sail one of our boats on Boston Harbor or to the islands whenever you’d like.

Courageous offers a variety of memberships to fit you schedule, skill level, and boat preference — check out the different options, and see which one works best for you. Our sailing area extends out around the Harbor Islands for qualified members.

As a Courageous member, you’ll be a part of an enthusiastic, inclusive community of sailors…and you’ll be helping Courageous provide free and low-cost sailing opportunities for Boston kids.

Member Area

Courageous is open noon – sunset on weekdays and 10 – sunset on weekends and holidays, May 1 through October 31. Boat availability is usually plentiful, but is not guaranteed so we always encourage members to reserve a boat ahead of time.

Membership Benefits

In addition to access to a growing fleet of sailboats for from May through October, you’ll find a welcoming community on and off the water. Members receive discounts on certain courses, event tickets, first access to Courageous events, and discounts through some of our partner programs. From May through October, Courageous runs lots of Member programs including:

Discounts on Courses

As a member of Courageous you will receive up to 20% off certain courses, plus discounts for certain event tickets. Keep an eye on the event calendar for upcoming events on Pier 4!

Island Camping Trips

Set sail for an island with a boat full of camping gear, good food, and friends – thats the essence of the Courageous Camping trips. These are wildly popular, so keep your eyes out for an email for our next trip and be sure to sign up early to make sure you (and your crew!) can enjoy an overnight adventure in the Boston Harbor Islands.

Moonlight Sails

Can you imagine a better night than sailing under the stars? This is your chance to experience Boston Harbor by moonlight in one of our boats. Several nights a year we take out a fleet of Rhodes 19’s and J22’s for a couple of hours in the harbor – all are welcome but a yellow flag rating or higher is required to be at the helm.


Racing is a vibrant scene at courageous in the spring, summer, fall, and winter! We offer beginner & intermediate Rhodes 19 racing, advanced racing in Rhodes 19’s and Lasers, match racing clinics, and frostbite racing. Courageous also provides Race Committee support for Wednesday evening PHRF racing in the harbor and we’re home to the biggest PHRF party of the summer – the annual Barefoot Regatta.

Learn more about racing

Advance your sailing skills

Lessons for Members

If you are new to sailing or if you’re picking it back up after many years ashore, we are excited to help you get comfortable taking the helm of a boat. A great place to begin is with a four day Basic Keelboat Course. Most graduates of this course pass their red flag certification, which is the minimum requirement to take a boat out as a Courageous member.

If you don't need a full course but are  looking to brush up on a few skills before taking the helm on your own, members receive 50% off private lessons, contact to book your lesson today.

Find your course

On the Water Check-outs

Sailors with experience may be able to get out on the water by taking a flag test. Flag ratings are required for every member and must be taken annually. Courageous has three flag ratings:

Red flag – beginner
Yellow flag – intermediate
Green flag – advanced

Members can progress from level to level in a number of ways, contact us to find out more!

Learn more about flag ratings