Boston Freedom Trail to Harvard Square Private Driving Tour

  • 4-10 Hours
  • Driving Tour
  • Group price up to 6Groups of 7+ call to book
  • Private Tour
  • Daily


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!

Community Impact

We are committed to a “360-degree view” of storytelling, featuring stories about underrepresented groups, such as women, immigrants, and people of various ethnicities, ages, religions, and sexual orientations.

During our visit to the towns of Lexington and Concord, we will provide recommendations and offer opportunities to patronize small and local businesses.

Your guide will speak of the important role Concord played in the Underground Railroad and how one of the town’s most prominent families of their day served as a refuge for many people escaping slavery.

You will learn about the ongoing efforts by locals who are protecting historically and environmentally significant places including Walden Pond and Walden Woods.


Freedom Trail

You’ll be discovering the history of the United States at several locations along this famous trail in Boston with a knowledgeable local guide to bring history to life!

Faneuil Hall Marketplace

 Originally built as a public market house and assembly room, this landmark has more recently served as a site of significant speeches and houses unique shops, food stands, and more.

Fenway Park

Our tour will pass by this world-renowned baseball stadium, home of the Major League Baseball team Boston Red Sox since 1912!

Massachusetts State House

You’ll love seeing the glittering dome of the inspiring, historic, and beautiful Massachusetts State House, designed and built by famous federalist architect Charles Bulfinch in 1798. From the outside, take in the views of modern Boston, including the skyscrapers of downtown, the Financial District, and the tallest building in New England: The John Hancock Tower.

Old South Meeting House

You can’t come to Boston and not mention the Boston Tea Party. This location, in-fact a church, is where it all began – one night in 1773, when it was the largest building in the city! Stop here with your tour guide to learn more about this historic building.

Granary Burying Ground

 Originally part of Boston Common, this cemetery dates back to 1660. During your Boston Freedom Trail tour, you’ll pass by the final resting spot of famous Revolutionary heroes like John Hancock, Paul Revere, and Sam Adams.

Quincy Market

We’ll pass by this national historical landmark on our Boston history tour to learn more about the early days of the market and how it has transformed over the years.

Boston Seaport

This newer Boston neighborhood draws visitors for its city views and shopping. We’ll stop here on our tour to enjoy its harbor views, artwork, and restaurants – your tour guide will have recommendations on where to get some great New England seafood!

Boston Harborwalk

Enjoy views of Boston along this peaceful shoreline walkway around the Boston harbor. 

Boston Public Library

This gorgeous landmark was established in 1852 as the first free library in America and its vast collection of millions of books, artifacts, and more make it the third-largest public library in the United States.

Trinity Church

An excellent example of Richardsonian Romanesque style, this work of art and architecture was built between 1872 and 1877, and its intricate exterior and interior is sure to impress anyone!

Make Way for Ducklings Statues

We can stop at Boston’s most beloved sculpture, Make Way for Ducklings, based on the 1941 children’s book written and illustrated by Robert McCloskey.

Harvard Square

 Your Boston driving tour will include a stop at the plaza in the heart of Harvard Square, which serves as a meeting point for local residents and, in particular, Harvard students, who come here to enjoy the area’s many stores, coffee shops, and entertainment venues.

U.S.S. Constitution

 The oldest commissioned ship in the Navy, U.S.S. Constitution, sits in the waters off the Charlestown neighborhood and can be toured for more information about its illustrious history.

Mount Auburn Cemetery

This beautifully landscaped cemetery – the first garden cemetery in the United States – serves as both a resting place for many notable Boston elites as well as an arboretum for a variety of trees. Find out from your local tour guide what sets this National Historic Landmark apart from other cemeteries!

Price Includes

Price Excludes

  • Local English-speaking guide
  • Private Transportation
  • Food and drink
  • Museum/site admission
  • Souvenir and guide gratuity

Pickup Information

Start times: We offer pickup anytime from 9am-2pm

Pickup: This tour offers custom pick up and drop off (hotel,airports,etc)


Driving Tour

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