Community Boating’s boathouse sits on the Esplanade at the foot of Beacon Hill, and its fleet of small sailboats scattered across the Charles River Basin is one of the city’s signature warm-weather sights. This is America’s oldest public sailing program, and the orientation is where every new sailor starts: a dockside tour of the boats and facilities, a walkthrough of how the teaching program works, and time for questions — no membership required to attend.

From there, the beginner path is famously quick: a pair of short on-land classes covering rigging and sailing theory, then a guided sail, and soon you’re taking a boat out with the skyline off your bow. The season runs spring through fall on tiered memberships that include classes and equipment. Landlubber adults are the target audience — no experience, gear, or boat ownership needed.