Five Places to Take Sailing Lessons in Boston

Whether you’re a rookie or a salty dog, your sailboat journey starts here.

Illustration by Jeannie Phan

For Smooth Sailing

Community Boating

From its perch on the Charles River Esplanade, Community Boating is responsible for the sailing dinghies dotting the river that have become an iconic Boston image. Incorporated in 1946 with the goal of providing accessible, inexpensive sailing opportunities, little has changed about this program except for the expansion of its offerings. There are classes for both adults and kids, from beginner to advanced levels, and for experienced sailors, four-passenger sailboat rentals are available to the public from April through October.

21 David G Mugar Way, Boston,

For Technical Instruction

Boston Sailing Center

When the weather’s fine, you might want to get right out on the water—but not so fast. This organization’s “Learn to Sail” course takes place in a classroom on Lewis Wharf before students head out onto Boston Harbor in a Sonar, one of the fleet’s fourteen 23-foot-long boats. You’ll sail to Boston’s outer harbor on the last session of the course, then you’ll complete the written American Sailing Association (ASA) test to receive your sailing certification.

For a Confidence Boost

Courageous Sailing

Heralded for its summer day camp for kids ages 8 to 15, Courageous Sailing views the sport as a platform to develop leadership skills, gain confidence, and enhance personal growth while exploring the marine environment on keelboats, dinghies, and 420s. Based at Charlestown’s Pier 4 and on Jamaica Pond, the organization also offers adult sailing programs that range from beginner to advanced, and there are navigation and cruising courses that teach the essentials of larger boat handling. Once you have your sea legs, you can try racing on 19-foot Rhodes and 14-foot Lasers—also a big part of the Courageous Sailing culture.

For Building Community

Piers Park Sailing Center

Located on the East Boston Waterfront, this community-centric program is devoted to inclusive and adaptive programming. Youth programs are designed to increase science literacy and resilience while fostering an environment of mentorship, while summer and after-school programs start at age 10 with on-the-water skill building in basic keelboats. Adult fundamental courses, meanwhile, are conducted on the center’s fleet of 23-foot Sonars; upon completion, you’re eligible to sail the fleet’s boats on your own with a sailing pass.

For Experience on Larger Boats

First Reef Sailing

Run by lifelong sailors Paul Sullivan and Forrest Hardy, First Reef opened in 2022 with the goal of providing ASA certification courses, clinics, and a group of people who could sail together. Instruction takes place on 26-foot Colgate day sailers, and “on land” classes, including Intro to Navionics and Intro to Passage Routing, are also offered. Not sure if you want to commit? Sullivan and Hardy also host open houses at their outpost in the Boston Harbor Shipyard and Marina.

First published in the print edition of the June 2024 issue with the headline, “The Life Aquatic.”