Lesson or Harbor Cruise for Four, or a Keelboat Course and Membership at Courageous Sailing (Up to Half Off)


98% of 54 customers recommend

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In a Nutshell

Under instructor supervision, guests sail 19-ft. Rhodes sailboats, cruise Boston Harbor, or take steps toward sailing certification

The Fine Print

Promotional value expires Jun 30, 2013. Amount paid never expires. Limit 1 per person, may buy 3 additional as gifts. Valid only for option purchased. Must sign waiver. Slots will be open 5/1/13 through 9/30/13. Reservation req'd by 6/30/13, subject to availability. May begin booking 1/15/13. One week cancellation notice required or $30 fee for sailing option or $100 fee for course option may apply. Subject to weather. Keelboat courses consist of four six-hour days over two consecutive weekends. Must pass course in order to take out boats without an instructor. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Courageous Sailing - Charlestown: Lesson or Harbor Cruise for Four, or a Keelboat Course and Membership at Courageous Sailing (Up to Half Off)

Sailing on international waters allows sailors liberties that can't be taken on land, such as naming a dog a swearword or rebroadcasting NFL games without the written consent of the league. Go above the law with this Groupon.

Choose Between Two Options

  • $95 for a two-hour sailing lesson or harbor cruise for up to four (up to a $190 value)
  • $575 for a 24-hour basic keelboat complete course and a two-month sailing membership (up to a $1,150 value)

Seasoned instructors captain Courageous Sailing's fleet of 19-foot Rhodes sailboats on Boston Harbor, initiating students in the ways of the sea during private two-hour sailing lessons. Seafarers learn the ropes of steering and operating sailboats, confidently taking the tiller under instructor guidance to navigate the waves without trying to saddle up a whale. For a relaxing evening, groups can opt to let the captain steer while they enjoy the scenic, salty waterscape.

The basic keelboat complete course gives participants a solid grasp of the fundamentals of sailing, prepping them to take certification exams at the end of their training. An included two-month membership, which is activated on the last day of the course, grants access to the entire 24-boat Rhodes-19 fleet so fledgling sailors can put their skills into practice.

Though this merchant sometimes offers a discounted price online, this Groupon is still the best deal available.

Courageous Sailing

Some people may see sailing as a way to save money on gas when traveling by water, but Courageous Sailing, recognized as a top 10 community sailing center by US Sailing and Sail Magazine, sees it as a way to educate, build leadership skills, and promote life-long learning in youth, adults, and the physically disabled. Since 1987, the nonprofit organization has hosted sailing programs for Boston's youth along with providing accessible sailing lessons and membership to the community at large. The Courageous staff serves numerous children a year with their curriculum, which teaches kids personal responsibility, communication, problem solving, and teamwork through sailing. They’ve also hosted local Special Olympians, as well as weekly races for visually impaired youths through their partnership with The Carroll Center for the Blind.


98% of 54 customers recommend

  • “Loved it!!!!!!!”

  • “My family enjoyed the afternoon, highly recommended.”

  • “Great!”

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    Pier 4, Charlestown Navy Yard

    Charlestown, MA 02129


    Get Directions

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