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The 7 Best Boston Tours You Can Book Right Now

Boston Harbor Skyline

Visitors to Boston are sometimes surprised at how compact the city is. But it’s usually a pleasant surprise, because that means it’s possible to see most of the city’s sights in a single day—if you’re on the right tour. Here are the 7 best Boston tours for exploring the city from all different angles, from a walking Freedom Trail tour with a costumed guide to a food tour that lets you chow down on the North End’s best pizzas.


Freedom Trail Tour from Histrionic Academy

The 2.5-mile-long Freedom Trail Boston passes by more than a dozen locations that played crucial roles in America's fight for independence from the British. You'll take in the site of the Boston Massacre, tour Paul Revere's house, and walk among the headstones in the city's oldest burial ground.


River Sightseeing Tour from Charles Riverboat Company

This relaxing cruise takes you on a guided tour of the Charles River, which separates Boston proper from Cambridge and other towns. You can see a surprising number of sights from the water, including Beacon Hill, MIT, and Harvard, and you’ll share the water with plenty of rowers.



Hop-On, Hop-Off Trolley Tour from Cityview Trolley Tours

You’ll see just about everything on this hop-on, hop-off tour, which passes top sights including the Old State House, Charleston Bridge, and Boston Common, with guides dispensing facts and history all the way. You can also check out the Boston Wax museum (included) or book a harbor cruise at a discounted rate.

People on scavenger hunt


Scavenger Hunt from Operation City Quest

You'll have no idea what you'll see on this tour—and that's the point. There are 140 objects scattered around Boston for you to find, learn about, and document on your phone, so all the sightseeing is up to you.


Pizza and Taverns Tour from Boston Pizza Tours

Part history lesson, part culinary crawl, this walking tour takes you through the North End and downtown, where you'll sample authentic Italian pizzas and sip pints in the same bars where heroes of the Revolution made their plans to defy British rule.

Boston harbor


Sunset Harbor Cruise from Boston Green Cruises

Boston Harbor provides some of the best views of the city’s skyline, and the sunset makes for a beautiful backdrop during this hour-long cruise aboard a low-emission vessel.

Gray Line Trolley


3-Hour Trolley Tour from Gray Line Boston

A standout among Boston trolley tours is this 3-hour outing, which includes plenty of time for pictures at stops such as Copley Square, Fenway Park, and Charlestown Naval Yard (home of the USS Constitution). When you’re not snapping selfies, listen up for stories about the Freedom Trail, Back Bay, and more.

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Tour guide in costume4 Reasons to Do the Boston Freedom Trail

You can drink in the same bar Paul Revere and George Washington did, for one.
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