• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond
  • Work at Courageous

    The 2015 season is just around the corner, which means there is an opportunity for you to come spend your summer working at Courageous. You'll be outside and on the water with a great staff and sailors from age 8 and up. This could be the start of your lifelong passion for teaching sailing, educating, and organizing in your community. Read More
  • Leadership + Growth

    Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Read More
  • Environmentalism at Courageous

    Courageous is wind powered, but we do more than just use natural energy sources. For the past several years, our young sailors have been learning about marine biology and ocean cleanup from our own Environmental Educators and award-winning partners. Read More
  • Support Courageous Kids

    As 2014 draws to a close, Courageous is celebrating a successful year of teaching sailing and more to Boston kids, and looking ahead to next year. Please consider supporting Courageous in our mission to provide high-quality summer learning opportunities for the kids who need them most by making a tax-deductible donation to our Annual Appeal before December 31. Read More
  • Awareness Campaign

    See our new awareness campaign made by Hill Holliday and Courageous board member, Joe Berkeley. The campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids. Read More

img home 2hour

The easiest way to get out on the water.

No experience required!

Regular Price: $190

Black Friday-Cyber Monday: 50% OFF!

If you're looking for an relaxing, affordable way to give sailing a try or check out Courageous, this is it! The two-hour sail is an opportunity for up to 3-4 people to experience the fantastic views from Boston Harbor, learn some sailing skills, or just sit back and enjoy the ride on a comfortable, stable nineteen foot keelboat. An expert instructor will be there every step of the way, and will be happy to customize the experience for you. If you'd like a private lesson (beginner or advanced), no problem--you'll be amazed by how much you can learn in just two hours. If a leisurely cruise or harbor tour is more your style, great! Or combine the two for a fun, unique experience. Feel free to bring a picnic or snacks for the sail (note that alcohol isn't permitted before or during sailing). Life jackets are provided.

To schedule a sail on a J/22 or one of our larger cruising boats, or a sail lasting longer than two hours, please contact us directly.

If you enjoy your sail as much as we believe you will, Courageous makes it easy to keep sailing with discounts for anyone who is introduced to us through a 2-hour sail! Sign up within a week of your sail, and get a $45 discount on a 12-hour course, or a $95 discount on either a Basic Keelboat Complete course or a Full or Family membership. Please contact us directly to take advantage of this offer.

Purchase + Schedule

 

 

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Looking for information about reedeming a 2 hour sail purchased online from Amazon Local or Living Social? Click here.

Fear and 420s
Youth Program
For most Courageous students, their first day of step 4 is their first time in a dinghy, a transition from a stabile Rhodes 19 to a more responsive 420. This transition isn’t easy. The rounded lines of 420 belie how uncomfortable it is to sail—you’re guaranteed to sit on a cleat and bump your shin o...
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Home Away from Home
Youth Program
For this past summer, and the previous three, I worked in the Swim Sail Science (SSS) program at Courageous. In Swim Sail Science, we work with third and fourth graders from three schools: the Harvard Kent, Orchard Gardens, and the Warren Prescott. Their time in our youth program was split between s...
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Highlights from the 2015 Summer Youth Programs
Youth Program
BBQ with the Mayor Today the 2015 summer youth programs come to an end. We would like to take this opportunity to thank everyone who helped make this a summer a success. Our incredible instructors have taken the time to write about their experiences at Courageous, which we will be sharing weekly th...
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Tale of a Trip on a Tall Ship, by Ian Hay
Youth Program
“I’ll clear one question up for y’all before you ask it because I know you’re going to eventually,” said the thin and soft-spoken cadet, “that fuzzy stuff up on the rigging is called baggy wrinkle; we make it from old dock lines and it’s used as chafe protection for our sails.” From the aft deck of ...
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Courageous Summer Preview
Adult Program
It's time to think about summer! Winter is officially over, and only a few weeks remain until we open our doors for the 2015 season on May 1st! We have been working hard to increase programming this winter and build our fleet. Read on to catch up on the latest the Courageous adult program has to of...
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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129

 

 

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