• Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • 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
  • 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
  • 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
  • Environmentally Friendly

    Courageous is wind powered, but we do more than just use natual energy sources. For the past several years, our youngsters have been learning about marine biology and ocean cleanup through award winning partner programs. Read More

img home 2hour

The easiest way to get out on the water.

No experience required!

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. Normally $190, we are offering this during Open House for $135. 

Purchase + Schedule

 

 Individual Admission Option

For those who want the same experience at an even more accessible price, we offer individual admission as well! Normally $95, we are offering this during Open House for $60. 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.

Purchase + Schedule

 

 

livingsociallogoAmazon-Local

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

Step 4: Cruising learning lessons!
Youth Program
Written by Step 4 Assistant Leader, Ian Hay Today I regained my faith in adolescents’ possession of common sense. The day was intolerably muggy and boat assignments seemed dubious as I watched my students tack deep close reach to deep close reach up out of the Mystic. We had already narrowly escape...
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Welcome back to Environmental Education at Courageous Sailing!
Green
By Emily Hart, 2014 Environmental Education Program Coordinator: I’m excited for my first summer at Courageous as the Environmental Education Program Coordinator. We’ve had a great first week! We have two initiatives this summer to encourage staff and students to take positive actions on environme...
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Day 4 of the Challenge
Challenge
By Judith Krimski Ladies in da House! This intrepid reporter, AKA Master of the Obvious has noticed that WOAH! THE LADIES are dominating Corporate Challenge 2014. We racing sailors are all cognizant of the fact that sailing is a male dominated sport. I am reminded of this every time I go to a Lase...
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June 16- Day 3 Recap
Challenge
Monday, June 16. By resident Challenge Blogger Judith Krimski.  Yes, there was more of that sailboat racing stuff on Boston Harbor. Winds veering from easterly sea breeze to SW. It never fails. Just another stellar night on Boston Harbor and my "happiness quotient" is a solid 9.99999. Every t...
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Corporate Challenge - Night 1 - June 2nd
Challenge
Wind: South 8-10 knots with some higher gusts. Windward/leeward course was set from North to South. W4s were the call of the night. Fleet consisted of nineteen Rhodes 19s. We get all sorts of people who enjoy sailing at Courageous: kids in summer programs, families, young adults studying at local...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129

 

 

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