Give the Gift of Sailing!

It's the season of gift giving and what better way to show someone you love them than to give them an experience that lasts a lifetime!

Our most popular gift is back!  Save 50% on 2-hour-sail Private Sails on Boston Harbor until 12/31/23.

Private Sails & Harbor Cruises
Don't miss out on the best way to save!

Are you new to Courageous or the sport of sailing? Our bundles are the best way to join and save! 


The Courageous Experience:

Beyond sailing lessons and memberships, Courageous is a community that has something for everyone. 

If you're not sure where to start, check out our 2-hour sail options!  

Looking for something to wrap? Pair your experience with some of our Club Gear. 


Courageous Gear!


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 5 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!


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. Also discounted for Black Friday, our Mid-Fleet Performance 1 course will give you a firm foundation in Performance Sailing as well as prepare you to take our Mid-Fleet Cruising checkout.

Private Sails, Cruises, and Additional Sailing Courses

Whether you're looking for an intimate date night far away from the crowds or a customized lesson to brush up on your skills, we've got you covered. Join us for 2 hours on the water in 2021, and we promise you'll leave stress and worry on the dock.