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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.

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  • 2-Hour Private Lesson or Harbor Cruise just $95!

    If you know someone who would love to give sailing a try (or take their skills up a notch with a private lesson), this is the perfect gift! This two-hour sail is an opportunity for up to 3 or 4 people to experience the fantastic views from Boston Harbor, learn some sailing skills at any level, or just sit back and enjoy the ride on a comfortable, stable Rhodes 19 keelboat. An expert instructor will be there every step of the way, and will be happy to customize the lesson or cruise. Read More
  • 20% off our introductory Basic Keelboat Complete course

    In just 2 weekends, our Basic Keelboat Complete course will give a total sailing novice the opportunity to learn all they need to sail on their own, for just $440. This hands-on 24-hour US Sailing course is taught by one of our expert instructors in a 19 foot keelboat with up to 3 students. Combine the course with a Full or Family membership (25% off!) so that the newly minted skipper will be able to sail at Courageous all season long. Read More
  • 25% off Full Individual and Family Memberships

    A Courageous membership means that you can take one of our boats out for a sail on Boston Harbor whenever you’d like. Mem- bership also includes much more: barbeques, racing, fireworks- watching parties, moonlight sails, Harbor Island camping trips, and discounts on courses. You’ll be a part of an enthusiastic, inclusive community of sailors...and you’ll be helping Courageous provide free and low-cost sailing opportunities for Boston kids. Read More
  • 15-20% Off All Other Courses and Memberships

    Know somebody who’s ready to take their sailing skills up a notch, or who is looking for a way to get out on the water without the hassle and expense of boat ownership? Courageous has a variety of courses, ranging from a 12-hour beginner course to Advanced Keelboat to Bareboat Cruising, to challenge sailors of any level. Our different memberships offer access to the boats in our fleet, so that old salts and graduates of our courses can sail Boston Harbor in style. Read More
   
 

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Contact the Adult Program

 

Jake Denney

Adult Program Director
adultprogram@courageoussailing.org
617-242-3821 x14

DISCLAIMER: Courageous’s sailing season runs from May 1 to October 31. Basic Keelboat Complete course must be taken over two consecutive weekends, Saturday and Sunday from 10-4:30 each day, and completed before October 31. At the conclusion of your course, you’ll need to demonstrate competency and knowledge of sailing basics in order to sail as a member. Courageous membership includes access to our fleet of 25 Rhodes 19 keelboats, plus free or discounted member activities like cookouts, camping trips, moonlight sails, racing, and more.