In celebration of the United States’ 250th anniversary and Boston’s maritime history, Sail Boston 250 will draw millions to Boston Harbor as a majestic fleet of tall ships sail in.
From July 11 to 16, a fleet from over 25 countries will be viewable from land — but for an up-close experience, you can learn to sail and take to the water yourself.
Ahead of the six-day bicentennial event, numerous sailing schools around the Boston area offer courses for all skill levels.
Adults new to sailing can enroll in the Beginner Mercury Classes. This program encompasses an orientation to fundamental concepts, a rigging class, a shore school utilizing a simulator, and a guided sail — an opportunity to get that first-time, on-water experience. An adult intermediate class and two advanced classes are also available.
For youth, CBI offers the Summer Junior Program, featuring classes beginning in June, taught by nationally certified, world-class instructors.
Where: 54 Lewis Wharf, Boston
The Boston Sailing Center, New England’s oldest sailing school on Boston Harbor, provides courses accredited by the American Sailing Association.
For novices, the Learn to Sail course is the recommended starting point, where the primary objective is for students to become comfortable sailing within Boston Harbor and the Boston Harbor Islands National Park. The curriculum covers safe harbor navigation, including managing ship traffic, weather planning, boat handling, and sail trim.
Where: Charlestown and Jamaica Pond
Courageous Sailing offers comprehensive Learn to Sail courses, taught by expert U.S. sailing-certified instructors. The ultimate goal is to equip students to achieve a “red flag” rating, which allows them to check out a boat independently, without an instructor. These courses are kept small, with a maximum of three trainees per boat.
Where: 95 Marginal St., East Boston
Piers Park Sailing Center’s Learn to Sail course offers hands-on lessons with expert instructors who simplify the fundamentals, making sailing accessible while teaching all necessary basics. Upon completion, students are eligible to use Piers Park’s sailboats, provided with a valid sailing pass.
Where: 256 Marginal St., East Boston
For beginners, First Reef Sailing School provides the Basic Keelboat, a three-day course that begins in the classroom before moving on to on-the-water sailing practice and maneuvers. Intermediate and advanced sailors can choose from a variety of other courses.
For a shorter format of training, the center also offers sailing clinics, which cover specialized topics like night sailing and passing routing.
Where: 134 Memorial Dr., Cambridge
The Charles River Sailing Academy, located at the MIT Sailing Pavilion, is now open for registration for summer 2026. MIT Sailing Coach Mike Kalin and his staff will conduct beginner and intermediate sailing lessons for 11- to 16-year-olds.
The program consists of eight four-day sessions, running from the first session on June 8 until the end of August.
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