• 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 for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    We’re gearing up for another awesome summer of sailing at Courageous and Jamaica Pond! Our 2016 programs will run between Tuesday, July 5 and Friday, August 12. The lottery for registration opens March 1 and closes March 15. Although our website is currently under construction in preparation for registration, read on to learn more about our youth programs; please note that some details and dates will be updated for 2016. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More

img home 2hour

The easiest way to get out on the water.

No experience required!

Price: $190

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.

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

Learning the Ropes
Youth Program
I had a great summer at Courageous Sailing and have had a number of memorable experiences with kids on the water. One that stands out most to me happened with a student in Step 2. This student was always his own person and has a very colorful disposition but, because of this, had trouble showin...
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Mi Barco es Su Barco
Youth Program
The Swim Sail Science! program at Courageous this summer was very different than the summer youth programs that we have always had. Half of the students' summers were spent in math and reading classes, where they learned about different water systems and our limited supply of fresh water i...
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Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
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Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
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More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129

 

 

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