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Boston Freedom Trail to Harvard Square Private Driving Tour

Quick Details

4 hour Private tour
5 hour Private tour
6 hour Private tour
7 hour Private tour
8 hour Private tour
9 hour Private tour
10 hour Private tour

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  • Visit Freedom Trail sites like Faneuil Hall, Paul Revere House, & Boston Common
  • Drive through scenic neighborhoods like the North End, Back Bay, and Charlestown
  • Relive American history at the sites of the Boston Massacre and Boston Tea Party
  • Explore Harvard University’s campus and visit Harvard Square and Memorial Church
  • See top Boston sites like Fenway Park, Boston Public Library, and Charles River


  • Local Guide
  • Private Transportation

Not Included

  • Food and drink
  • Museum/site admission
  • Guide gratuity


Boston is a magnet for history buffs as well as architecture lovers, and we’re ready to nerd out with our travelers on this Boston driving tour that ventures past all the must-see historic stops in Beantown!

We’ll be exploring significant moments of American history along the iconic Freedom Trail, including landmarks like Faneuil Hall, where the first cries for revolution rang out. Your local tour guide will key in on the events that led to the American Revolution, like an infamous tea party and a pivotal massacre.

Boston is known for many of the nation’s “firsts”, including the very first free public library as well as the first public school in the U.S. and where you’ll learn how this pioneering institution connects us to modern-day public education.

A short drive over to Charlestown will bring us to both the Bunker Hill Monument and the U.S.S. Constitution, the oldest commissioned ship in the Navy. We’ll also be driving through beautiful Beacon Hill, stopping to see the most photographed street in all of Boston!

In Boston’s North End, you’ll discover amazing history from colonial times to modern crimes and get the best recommendations from your guide for the best cappuccinos and cannoli. And as you step inside historic Old North Church (when possible), you’ll learn what really happened during that legendary midnight ride…

If it’s seafood you’re seeking, you’ll find that and more in the Seaport District, where we’ll enjoy sweeping views of the Boston Harbor. More views abound along the banks of the Charles River, where we can take in the city skyline on the Boston Esplanade. See the beautiful Victorian-era homes of the Back Bay and learn how it got its name.  

Finally, we’ll complete our Boston tour at Harvard Square and walk around the country’s most prestigious university campus.

With so much history, culture, and great cuisine, we can’t wait to take you on this action-packed Boston sightseeing tour!