Open House Sale

April 22-April 30

10-50% OFF courses and memberships

Spring into the season!

As we kick off the season with our Annual Open House events down by Pier 4, we welcome you to join us in the fun (and savings) with our final sale prices for 2022. 

We will be hosting our in-person events at a neighboring pier (Charlestown Marina, by Pier 6 restaurant) and hope to see each of you there. If not, our savings can also be found here and last all week long!

If you are looking for a unique gift to give for mothers day or fathers day, or a new and fun reason to join us on the water this season, this is it!

Enjoy 10-50% off courses, membership, and Harbor Cruises. 


Private Lessons & Harbor Cruises

The perfect adventure or experiential gift this summer!

Whether you are purchasing for yourself or someone else, you can't go wrong with a 2-hour personalized experience on Boston Harbor.

Check out our 2-hour sail options!

Rhodes 19 Core Fleet

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.

Mid-Fleet Cruising

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 four J80s and a Tanzer.


For many, the Cruising Membership is the most coveted membership tier. The cruising fleet gets you out farther, faster, and for longer. Our 4 30'-35' boats have at least 2 berths and a head aboard, allowing you to cruise in comfort. Take a day trip to a harbor island or pick up a mooring for a night at sea. Memberships go quickly, so get yours before they are gone!

Learn to Sail

This is the best way to learn the basics! This course covers all you need to know to sail on your own at Courageous as a member. All Learn to Sail courses are taught in Rhodes 19s and are suitable for most ages and abilities.

Bundle & Save! Purchase our Learn to Sail 1 & 2 together and you'll save over $100. Add in a membership to save more than 50% on your membership price!

Intermediate Sailing

Ready to get out on some larger boats? Or maybe sail a little faster? We have some great deals on courses that will introduce you to performance sailing.

Meet the J80 is our aptly named, one-day clinic that will help you either get comfortable on a different boat after learning to sail on our Rhodes 19s or show you how to introduce this sportboat to others.