LOOK Die Bildagentur der Fotografen GmbH / Alamy
Samantha DiMauro
August 07, 2014

“America’s Walking City” didn’t earn its nickname for nothing. Most of Boston’s charm lies within easy walking distance; from the North End to Fenway is a scenic hour-long stroll of the city’s major landmarks, including the State House, the Public Garden, and the chic boutiques and cafes of Newbury Street. Tour operators, many of whom are acting professionals and trained historians, are entrenched in the city’s nearly 400-year-old history. They’re also keyed in to the latest developments (late night laws and hotel openings) and are ripe with local gossip. The best city tours are as entertaining as they are informative—an opportunity to explore the neighborhoods with a costumed guide looking vaguely like Paul Revere in his tri-corn hat and britches, or to cross the Charles River in one of the iconic rainbow-hued duck boats.

Urban AdvenTours

Shift your sightseeing into high gear on with a fleet of adventure-seeking cyclists.  Since founder Andrew Prescott began leading tours from his apartment one decade ago, Urban AdvenTours has become a familiar sight throughout the city, easily recognizable by the electric green fenders on custom-made city bikes. The original classic city view tour continues to cover the hallmark Boston sights, while a nature ride through the historic Emerald Necklace is prime for leaf peeping in autumn. Athletic history aficionados will love Paul Revere’s Ride to Freedom, where bikers are lead along the famed Midnight Ride.

Ghosts and Gravestones Tour

Get in touch with Boston’s dark side on this nightly, “frightseeing” trolley tour. A talented cast of sinister characters recounts the chilling legends surrounding some of the most haunted sites in Boston (Fort Warren; The Omni Parker House Hotel) and many guests have taken part in their own ghost stories. You may just walk away from a graveyard excursion with a photograph of a spectral spirit as a souvenir.

Boston Harbor Cruises

Founded in 1926, this cruise company has grown from a single boat to a fleet of 32 vessels, including ferries, catamarans, and speedboats. Take an easy-going trip across Boston’s working port, down the Charles River, and toward the bay to see both historic and contemporary landmarks like the Boston Light. For those seeking a more adrenaline-fueled tour, opt for the open ocean whale watch or an afternoon on “Codzilla,” the city’s singular punk rock speedboat tour. 

Old Town Trolley Tour

The old-fashioned, orange and green open-air trolleys are popular with visitors on mild summer afternoons. Enjoy the fully narrated ride through Boston on an old-fashioned, or use the service as “transportainment,” hopping on and off at the 20 major stops at your leisure. Old Town Trolley Tour tickets are good for two days, giving you ample time to explore the key highlights along the route, from the stuck-in-time bakeries of the Italian North End to the burgeoning Liberty Wharf Seaport District, home to the Institute of Contemporary Art and a number of modern, upscale restaurants. 

Boston Duck Tour

Ask any local or repeat tourist, and they’re likely to have experienced the quintessential Boston duck boat ride—on more than one occasion. Wind around the city and into the Charles River on a repurposed World War II-style amphibious DUKW vehicle; all while a very knowledgeable, comedic guide fills your mind with fun history and Boston trivia. Blow your duckbill whistle as loud as you possibly can at the Bostonians on the sidewalk as you ride by. They’ll love it. I swear.

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