Kayaking Boston | A Get-Started Guide

Want a fresh perspective on sightseeing (and a little fresh air, too)? Kayaking Boston offers a memorable way to experience New England’s marquee city.

By Yankee Magazine

Apr 02 2018


Kayakers and sailors take to the water in the Charles River Basin. | Kayaking Boston

Photo Credit : Lorianne DiSabato via Flickr/Creative Commons

Famed as one of America’s most walkable cities, Boston packs an impressive amount of history, architecture, and cultural appeal into its compact footprint (less than 50 square miles). In just one afternoon, you can cover a lot of ground — but you can cover a lot of water, too, if you try your hand at kayaking Boston.

kayaking boston
Kayakers and sailors take to the water in the Charles River Basin. | Kayaking Boston
Photo Credit : Lorianne DiSabato via Flickr/Creative Commons

The slow-moving, generally flat Charles River, which runs from Hopkinton to Boston, is ideal for laid-back floating. Upstream, there are wooded parks and a scenic six-mile “lakes district” filled with quiet coves and inlets. Downstream, the Charles bisects Cambridge and Boston and opens up into a broad basin that’s home to several rowing and yacht clubs. Here is where you’ll find the jaw-dropping city views, as the river runs past Boston’s Back Bay neighborhood and its lovely waterside Esplanade.

kayaking boston
Cruising one of the peaceful lagoons along the Charles River Esplanade. | Kayaking Boston
Photo Credit : Leslie_atFlickr/Creative Commons

Kayaking Boston Harbor, which connects to the Charles via locks near the TD Garden, is not for the faint-hearted. The waves and wind can be challenging — and then there’s the traffic. Ferries, cruise ships, and massive container ships all ply these waters. But kayakers can and do cruise the inner harbor, an activity that got a boost in 2011 with the opening of Fort Point Pier. Designed for nonmotorized watercraft, this public dock is a great put-in/take-out spot for those with their own boats. However you get to the harbor, though, the payoff is considerable: up-close views of Boston’s North End, downtown, and the Seaport District, as well as the USS Constitution in Charlestown.

kayaking boston
Low-key sea kayaking lessons at Spectacle Island help beginners experience the natural beauty of the Boston Harbor Islands National and State Park. | Kayaking Boston
Photo Credit : Courtesy of Boston Harbor Island Alliance/Photo by Tom Kates

For those ready to take kayaking Boston to the next level, about four miles offshore from downtown lies the edge of the Boston Harbor Islands National and State Park. The largest recreational open space in eastern Massachusetts, the park spans 34 islands and peninsulas. Its sprawl means that sea kayakers who are leery of launching from the inner harbor can choose from a variety of alternative put-in sites in Winthrop, Quincy, Hingham, and Hull. Not ready to tackle the open-water crossing to the Boston Harbor Islands? There’s a terrific (and free!) sea kayaking lesson offered on Spectacle Island on summer Mondays that’s suitable for beginners. All you have to do is reserve your spot and catch a ferry ride, and the rangers will help you do the rest.

Kayaking Boston | Outfitters and Resources

Paddle Boston/Charles River Canoe and Kayak

Known as the go-to for paddling fun in the Greater Boston area, this outfitter got its start back in the early 1970s. Today it operates five waterside locations renting canoes, kayaks, and standup paddleboards. Its Kendall Square location, in Cambridge, allows for easy round-trips onto the Charles River, or one-way trips to its nearby location in Allston/Brighton. The Cambridge outpost also hosts a wide variety of tours for visitors interested in kayaking Boston, from skyline and sunset outings to a trip into Boston Harbor. Named a 2011 Yankee Editors’ Pick for “Best Instant Getaway.”

kayaking boston
The Zakim Bridge soars above a tour group from Paddle Boston/Charles River Canoe and Kayak. | Kayaking Boston
Photo Credit : Charles River Canoe & Kayak

Community Boating

The oldest and largest community sailing program in the country has taught generations of Bostonians to tack and jibe. But if you’d rather dip a paddle than hoist a sail, you’ll still find fun at Community Boating. From April through October, the organization rents kayaks and paddleboats by the day, which can be taken out into the basin between the Longfellow and Mass. Ave. bridges. Beginners are welcome, though some age restrictions do apply.

kayaking boston
With the Prudential Tower punctuating the skyline behind them, kayakers in rentals from Community Boating enjoy an day of paddling on the Charles. | Kayaking Boston
Photo Credit : Community Boating Inc. Boston

Suburban Kayak Outfitters

There’s more to explore in the Greater Boston area than the city skyline and seaport. For instance, Boating in Boston runs five suburban locations that range from Hopkinton State Park in the west to Wakefield’s Lake Quannapowitt in the north; all offer kayak rentals and instruction, among other activities. On the North Shore, you’ll find a worthy option in Essex River Basin Adventures (named a 2016 Yankee Editors’ Pick for “Best Kayak Tour”). There, choose from a full menu of guided tours and learning opportunities that traverse the scenic Essex River Basin and beyond. On the South Shore, check out Nantasket Kayaks, whose Hull location is perfectly suited for exploring the Weir River Estuary and the pristine shoreline of World’s End.

Do you have any favorite tips for kayaking Boston? Let us know!

Skiing Near Boston | Where to Go
Hiking Near Boston for Those Who Love Adventure
7 Favorite Boston Seaport Restaurants