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Boston Freedom Trail to Harvard Square Private Driving Tour

5 (17)

Boston Freedom Trail to Harvard Square Private Driving Tour

5 (17)
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Experience the vibrant history and culture of Boston on this exhilarating half-day driving tour. Immerse yourself in the rich stories of America's independence as you visit iconic landmarks such as Faneuil Hall, the site of the Boston massacre, and the Boston Harbor where the colonists famously dumped tea. Explore the historic neighborhoods of Beacon Hill with its brick houses and cobblestone streets, and the North End with its delicious Italian eateries and local cafes. Discover the importance of preserving architecture in a booming city while passing by the Back Bay's Victorian-era houses. Marvel at the beauty of Harvard University's campus and soak in the atmosphere of Harvard Square. With a knowledgeable guide bringing history to life and highlighting the positive impacts of immigrant communities, this tour guarantees a unique and captivating experience of Boston's past and present. Don't miss the opportunity to savor an authentic Boston lobster roll and create memories that will last a lifetime.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 5 hours
  • Suitable for 1-6 Participants
  • Private Tour, Small Group Tour
  • Guided Experience
  • 360-degree view of storytelling
  • Supporting local businesses
  • Exploring immigrant neighborhoods
  • Preserving historic architecture
  • Visiting iconic landmarks
  • Explore Harvard University’s campus and visit Harvard Square and Memorial Church
  • Drive through scenic neighborhoods like the North End, Back Bay, and Charlestown
  • Visit Freedom Trail sites like Faneuil Hall, Paul Revere House, & Boston Common
  • See top Boston sites like Fenway Park, Boston Public Library, and Charles River
  • Private Transportation
  • Local, English-speaking guide
  • Custom pick up and drop off!
  • Not all locations listed are guaranteed stops
  • Food and drink, souvenirs, tips/gratuities for your guide

Popular Hotels Closeby

More about this experience


Experience the vibrant history and culture of Boston on this half-day driving tour. Designed for those looking to make the most of their time in the city, this tour will take you to the most iconic and historic spots in Boston. From Faneuil Hall to the Boston Harbor, you'll immerse yourself in the rich heritage of the city that played a crucial role in America's independence. Along the way, you'll visit renowned landmarks such as the Old North Church, Bunker Hill Monument, and the U.S.S. Constitution. Explore diverse neighborhoods like Back Bay and Beacon Hill, with their Victorian-era houses and picturesque streets. For food enthusiasts, we'll also make stops in the North End and Seaport District, known for their incredible food scenes, including the opportunity to indulge in an authentic Boston lobster roll.

What to Expect?

During this driving tour, you can expect to dive deep into the history and culture of Boston. You'll explore significant sites linked to America's independence and discover hidden gems in the city's neighborhoods. With a local, English-speaking guide, you'll gain insider knowledge and fascinating insights into Boston's past and present. As you drive through the city, you'll witness the juxtaposition of historic landmarks and modern architecture, creating a unique atmosphere that captures the essence of Boston. This tour offers a comprehensive overview of the city's highlights, ensuring you make the most of your time in Boston.

Who is this for?

This driving tour is perfect for history enthusiasts, culture seekers, and food lovers alike. Whether you're a first-time visitor or a seasoned traveler, this tour provides a captivating experience for anyone interested in exploring the historic spots and diverse neighborhoods of Boston. Families, couples, and solo travelers will all find value in this tour as it offers a well-rounded perspective on the city's past and present. This tour is inclusive and welcomes individuals with various interests and preferences, ensuring that everyone can enjoy and appreciate the beauty and significance of Boston.

Why Book This?

Embark on this driving tour to discover the hidden stories and untold secrets of Boston. With a knowledgeable guide leading the way, you'll gain a deeper understanding of the city's history and its impact on American culture. This tour allows you to cover a significant amount of ground in just five hours, providing a comprehensive overview of the city's most important landmarks and neighborhoods. From the bustling Harvard Square to the charming streets of Beacon Hill, you'll experience the authentic essence of Boston. Additionally, the opportunity to indulge in an authentic Boston lobster roll and explore the city's vibrant food scenes adds a delicious and unforgettable element to this tour.

Good to Know

During the tour, you'll be accompanied by a local, English-speaking guide who will share their insights and knowledge about Boston's history, culture, and architecture. Please note that food and drinks, guide gratuities, and souvenirs are not included in the tour price. It's recommended to wear comfortable shoes and clothing and bring along any necessary personal items. The tour will begin and end at the designated meeting point, providing convenient access to public transportation and parking options. Prepare to be captivated by the fascinating stories and enchanting atmosphere of Boston on this half-day driving tour.


Previous participants of this driving tour have praised its comprehensive itinerary and knowledgeable guides. Many have expressed their appreciation for the opportunity to explore both famous landmarks and hidden gems in Boston. Travelers have also raved about the chance to indulge in an authentic Boston lobster roll and experience the city's diverse food scenes. Overall, participants have found this tour to be a captivating and enriching way to explore the history and culture of Boston.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Your Itinerary


(Pass by)

-We are committed to a “360-degree view” of storytelling, featuring stories about under-represented groups, such as women, immigrants, and people of various ethnicities, ages, religions, and sexual orientations -Our guides prioritize “supporting local” through recommending and patronizing family-run and locally owned businesses so that culture and traditions are preserved and are passed onto the next generation -Throughout the driving tour, we will explore the various neighborhoods in which immigrant populations, sometimes welcomed and sometimes not-so-welcomed, have left permanent and positive impacts on the history and culture of our modern city -Your guide will point out the importance of preserving architecture in a booming city where instead of tearing down historic buildings, we have restored and created a city around them

Beacon Hill

Your Boston tour passes through one of the prettiest neighborhoods of Boston, Beacon Hill. Upon this hill resides Massachusetts State House and where streets are lined with brick houses, cobblestone streets, small shops, and significant historic landmarks.

North End

The neighborhood of Boston’s North End is not only known for its historic buildings – including Paul Revere’s home and Old North Church – but also its excellent Italian eateries and local cafes carrying locally roasted Beantown coffee.

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, chain stores, food stands, and more.

Charles River Esplanade

Following the Charles River along the banks of the Back Bay neighborhood, this esplanade attracts all sorts of recreation and leisure activities, including performances at Hatch Memorial Shell.

Back Bay

Built on reclaimed land originally part of the Charles River basin, this neighborhood is known for its luxury shopping, historic landmarks like Boston Public Library, and some of the city’s best preserved Victorian architecture.

Old North Church & Historic Site

Built in 1723 and the oldest standing church building in Boston, Old North Church played an important role in the city’s colonial days leading up to the American Revolution

Harvard University

Your Boston sightseeing tour can include a walk through this Ivy League university that is the oldest institution of higher learning in the United States. The school is known for its beautiful campus, historic buildings, many styles of architecture, movie filming locations, and its long history of notable graduates.

Bunker Hill Monument

(Pass by)

This granite obelisk, erected between 1825 and 1843, marks the pivotal 1775 Battle of Bunker Hill, one of the first major battles between the Red Coats and Patriots in the American Revolutionary War.

USS Constitution

(Pass by)

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.

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.



5 (17)


We had the most amazing experience ever thanks to Nabil! Nabil’s knowledge of the city and sites is second to none. We saw the most amazing things and received a truly exceptional guide to Boston. Nabil answered all of our many questions with incredible detail and facts. We highly recommended Nabil!


Nabil was our guide and was full of knowledge and history of the Boston area. He took the time to show our son Harvard and MIT at our request. Highly recommend him and this tour.


I am SO glad i took this city driving tour. Our guide was so personable and such a great storyteller. Kept us all engaged for the full 6 hours and knew every nook and cranny of the city. Will recommend this tour to everyone I know visiting Boston.

Akram S

I absolutely loved this tour and was extremely impressed by Nabil’s enthusiasm for the history of Boston. I saw everything I wanted to see and more. Nabil was an extremely safe driver too which made was quite different from driving tours we’ve done in other cities


This tour is 100% worth it. We saw so many sites and many of them hidden gems all throughout Boston. I was extremely impressed with this experience and would highly recommend Nabil, our tour guide. He was an excellent storyteller, very knowledgeable of Boston, a lover of history and with great comedic timing. I highly recommend this tour to anyone who wants to see all of Boston’s highlights and learn so much American history. It was a thought provoking day.


This tour completely exceeded my expectations. We decided to try this tour because it was too cold outside to be walking the entire Freedom Trail. We were so happy we did. Nabil did a wonderful job showing us everything we wanted and many things we didn't even know we wanted to see - all from the comfort of a spacious, clean and warm vehicle completely protected from the elements. Highly recommend!!


This tour is wicked awesome! We chose this tour because we only had one day to see the city and we didn't want to go on a walking tour (especially with some goofy costumed guide). We were picked up at our hotel and our guide drove us all over Boston and Cambridge. We saw a lot of the historical sights that we wanted to see but we also saw some amazing places that we would have never found on our own like this amazing bakery where we had incredible bread and various photogenic views of the city. Our guide was very knowledgeable of the area, sharing historical stories and hysterical tales. This was well worth the money!


Nabil was a really great tour guide! He took my group on a private tour of Boston and we had such a great time while learning all about the history of the town. We really couldn’t have asked for a better tour guide. Highly recommend!


Nabil did an amazing job on our tour of Boston when we were in town for a wedding. Our daughter just started 5th grade and she loved every minute of it... asked so many questions!


What a great tour! What a great tour guide! Nabil was, by far, the best guide we have ever had on a personal tour. If you’re ever in Boston, be sure to book a tour and ask for him. You certainly will not be disappointed.
Collected by Evendo, Tripadvisor & Viator
2024-04-15 22:23