Holiday Sales 2022 -
From December 9-Jan 1 you'll save 10-50% on our most popular lessons and memberships. Don't miss our biggest sale of the year!
If you're looking for even bigger savings this holiday season, check-out our daily "Highlight Reel Deals" featured on our instagram and facebook accounts.
Private Lessons & Harbor Cruises
The perfect gift for the 2022 season!
Whether you are purchasing for yourself or someone else, you can't go wrong with a 2-hour personalized experience on Boston Harbor.
Memberships
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.
full
- One registered skipper
- Access to 27 Rhodes 19s
- One year term
- Includes unlimited guests
family
- Two registered skippers
- Access to 27 Rhodes 19s
- One year term
- Includes unlimited guests
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.
Cruising
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!
Courses
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. 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.
Mid-Fleet Performance 1
- 2-day, 12-hour course on a J80
- Advanced sail trim and theory
- Refined boat handling
- Crew overboard and anchoring
Cruising Courses
Everything you need to sail bigger boats with confidence! All courses are taught on one of our cruising boats, ranging from 30' to 35'. Start with the basics-- we recommend the First Mate course!--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.
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.
