Except when frozen over, the waterways coursing through the city serve as a playground for boaters of all stripes. All types of pleasure craft, with the exception of inflatables, are allowed from the Charles River and Inner Harbor to North Washington Street on the waters of Boston Harbor, Dorchester inner and outer bays, and the Neponset River from the Granite Avenue Bridge to Dorchester Bay.
Boat Drop Sites. There are several boat drop sites along the Charles, including Clarendon Street, the Hatch Shell on Embankment Road, and Pinckney Street Landing (all in Back Bay); Brooks Street at Nonantum Road, and the Richard T. Artesani Playground, off Soldiers Field Road (both in Brighton); the Charles River Dam, at the Museum of Science in Cambridge; and Watertown Square, at Charles River Road in Watertown. Boston, Massachusetts. www.mass.gov/eea/agencies/dcr/massparks/recreational-activities/boat-ramps.html.
Charles River Watershed Association. This association publishes detailed boating information on its website. Boston, Massachusetts. 781/788–0007; www.charlesriver.org.
Head of the Charles Regatta. In mid-October about 400,000 spectators turn out to cheer the more than 11,000 male and female athletes who come from all over the world to compete in the annual Head of the Charles Regatta, which in 2014 marked its 50th anniversary. Crowds line the banks of the Charles River with blankets and beer (although the police disapprove of the latter), cheering on their favorite teams and generally using the weekend as an excuse to party. Limited free parking is available, but the chances of finding an open space close to the race route are slim; take public transportation if you can. During the event, free shuttles run between the start and end point of the race route on both sides of the river. Banks of the Charles River, Harvard Square, Cambridge, Massachusetts, 02238. 617/868–6200; www.hocr.org.
Lessons and Rentals
Boston University. From May to October, Boston University offers beginner to advanced rowing and sailing programs. Dewolfe Boathouse, 619 Memorial Dr., Harvard Square, Cambridge, Massachusetts, 02139. 617/353–9307; www.bu.edu/fitrec.
Charles River Canoe & Kayak Center. From May through mid-November you can rent a canoe, kayak, paddleboard, rowboat, or rowing shell from Charles River Canoe & Kayak Center. The center also offers a variety of canoeing and kayaking classes for all skill levels as well as organized group outings and tours. 2401 Commonwealth Ave., Newton, Massachusetts, 02466. 617/965–5110; www.paddleboston.com.
Charles River Canoe & Kayak Center's kiosk. From this kiosk you can rent canoes and kayaks from May through mid-October. If the weather is iffy, call ahead to see if they're open. Soldiers' Field Rd. near Eliot Bridge, 1071 Soldiers Field Rd., Allston, Boston, Massachusetts, 02134. 617/965–5110; www.paddleboston.com/boston.php.
Community Boating. Near the Charles Street footbridge on the Esplanade, Community Boating is the host of America's oldest public sailing program. From April through October, $99 nets you a 30-day introductory membership, beginner-level classes, and use of sailboats and kayaks. Full memberships grant unlimited use of all facilities; splash around for 60 days for $245 or all season long for $315. Experienced sailors short on time can opt for a one-day sailboat rental for $85; kayaks and paddleboards rent for $45 per day. 21 David Mugar Way, Beacon Hill, Boston, Massachusetts, 02114. 617/523–1038; www.community-boating.org.
Community Rowing. This organization teaches rowing courses from introductory to competitive adult and youth levels. Private lessons are also available. Harry Parker Boathouse, 20 Nonantum Rd., Brighton, Boston, Massachusetts, 02135. 617/779–8267; www.communityrowing.org.
Jamaica Pond Boat House. From May to October, Courageous Sailing operates out of the Jamaica Pond Boat House and provides lessons and equipment for rowing and sailing on the pond, except when youth classes are in session; call ahead to confirm. One-hour kayak and sailboat rentals are $20 (rowboats are $15; $10 with a fishing license). Cash or check only. Jamaica Way and Pond St., Jamaica Plain, Boston, Massachusetts, 02130. 617/522–5061; courageoussailing.org/jamaica-pond.