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The Boston Public Garden and the Boston Common are great ways to enjoy the city

After spending a few days in New York and Long Island, it was time to explore Boston. Known as the capital of the state of Massachusetts, this was one of my favorite stops of the entire summer road trip. Founded at the mouth of the Charles River and with a population of about 600,000 inhabitants, the city has played a fundamental role in the history and culture of the United States, being the birthplace of the well-known Kennedy. Interested in discovering what to see and where to eat in Boston?

What to see in Boston

We spent an evening and a full day in Boston. Check out our itinerary to inspire your next trip.

Buying a Charlie Ticket is the best way to get around Boston
Buying a Charlie Ticket is the best way to get around Boston

Prestigious universities

Boston is well known for its academia because both Harvard and the MIT (Massachusetts Institute of Technology) are located in the Cambridge area. Since they’re a bit far out and we arrived at dusk, we drove there with our rental car from New York and then dropped it off at the airport.

The MIT dome at night
The MIT dome at night

Newbury Street

We started our full-day visit to Boston in Newbury St, an elegant street lined with shops, restaurants and art galleries. Nearby is Copley Square, surrounded by some of Boston’s most distinctive buildings. On one side you will find Trinity Church, a masterpiece of neo-Romanesque art in the United States, made with granite and sandstone. The John Hancock Tower, a glass building which is the tallest in New England, is located in front of the church.

On the other side of Copley Square you’ll notice two magnificent buildings: the Gothic Old South Church and the Boston Public Library, housed in a beautiful Italian palazzo where we had breakfast (see section on ‘Where to eat in Boston’ below).

Old South Church
Old South Church
Shop along Newbury Street
Shop along Newbury Street

Boston Public Garden and Boston Common

Take your time to enjoy walking around the green lungs of the city of Boston: the Boston Public Garden and the Boston Common. Located side by side, these parks offer plenty of outdoor space to play, jog or take a boat ride. It was so lively and nice when we visited this summer but I imagine it must be equally beautiful in the winter time.

Cypresses in the Boston Public Garden
Cypresses in the Boston Public Garden

Beacon Hill

Right next to the Boston Public Garden and the Boston Common is the Massachusetts State House. Functioning as the seat of the state government, it served as a model for the Capitol in Washington DC. Its golden dome indicates the starting point for the state roads.

Does this golden dome remind you of something?
Does this golden dome remind you of something?

The iconic Beacon Hill neighborhood is located behind the Massachusetts State House. For decades, this was the most sought after in the city featuring steep streets and a succession of mansions and elegant federal-style townhouses.

An elegant street in Beacon Hill
An elegant street in Beacon Hill
This doggy seems to be out of service
This doggy seems to be out of service

Freedom Trail

The Freedom Trail was my all-time favorite during our day-visit to Boston. This pedestrian itinerary passes by historical places of interest related to the War of Independence and to the city itself. This four-kilometer trail is marked by a red line on the sidewalk and starts from Boston Common, winds through downtown and ends at Bunker Hill in Charlestown.

Freedom Trail sign on the sidewalk
Freedom Trail sign on the sidewalk
You can't get lost following the Freedom Trail!
You can’t get lost following the Freedom Trail!

Our first stop along the Freedom Trail was Park St Church, a stronghold of the anti-slavery movement. Continuing down Tremont St, we explored King’s Chapel -which was the main Anglican church in old Puritan Boston – and its tiny cemetery. Further down on School St, we came across a mosaic embedded in the sidewalk marking the location of the first public school, founded in 1635. Next to it is the Old City Hall.

Old City Hall
Old City Hall

Once on Washington St, we discovered the Old South Meeting House. This is where the heated rally that led to the Tea Party took place in December 1773. During this episode, the American colonists threw a whole shipment of tea into the sea in protest against the tax imposed by the metropolis on the import of this and other products. This event is considered one of the precedents of the subsequent United States War of Independence.
Just a few blocks away from this historic landmark, we found the Old State House, dwarfed by the construction of the financial district. This building was the seat of the British colonial government and was where the Declaration of Independence was read to the citizens of Boston in 1776.

Two bikes locked in front of Tremont Temple
Two bikes locked in front of Tremont Temple
Old State House in Boston
Old State House in Boston


Strolling through Faneuil Hall and Quincy Market, head north in order to get to the Paul Revere House, a famous patriot who alerted a neighboring town of the imminent arrival of British troops.
The Freedom Trail then crosses the North End and passes through the Italian neighborhood, Boston’s Little Italy. You’ll find plenty of Italian restaurants, cafés and shops here, especially along Hanover Street.

Italian restaurants abound in Boston's North End
Italian restaurants abound in Boston’s North End


Crossing the iron North Washington Street Bridge over the Charles River you’ll reach Charlestown, where the Navy Yard is located and the USS Constitution is docked. You can even access the deck or visit the museum.
Our last stop on the Freedom Trail was at the Bunker Hill Monument, which commemorates a battle of 1775.

USS Constitution
USS Constitution
A statue in front of the Bunker Hill Monument
A statue in front of the Bunker Hill Monument
Boston harbor
Boston harbor

Chinatown, the Theater District & Back Bay

After the succulent dinner at Legal Sea Foods (see details below), we strolled through the docks and piers of the waterfront, we explored Chinatown and the Theater District and we returned through the Back Bay neighborhood. This is now the most exclusive one in Boston, and in case you’re interested, where supermodel Gisele Bündchen lives with Tom Brady and their kids.

Where to eat in Boston

If you’re looking for places to eat in Boston, find my recommendations below:

  • Boston Public Library: we came here for breakfast and we loved it. The beautiful interior of this Italian palazzo is a great spot to kickstart your day!
How gorgeous is the patio at the Boston Public Library?
How gorgeous is this patio at the Boston Public Library?
  • Legal Sea Foods: if you’ve been in the United States for a while, chances are you’ve eaten at this seafood restaurant chain. With several venues in Boston, we had dinner at the one in Long Wharf (255 State St). Located right by the harbor, we tried the famous lobster for dinner and we even had a bib and a nutcracker.
Legal Sea Foods was our spot for dinner after a long day of walking around Boston
Legal Sea Foods was our spot for dinner after a long day of walking around Boston
Calamari, mussels, corncob and lobster at Legal Sea Foods
Calamari, mussels, corncob and lobster at Legal Sea Foods

Trip details

  • Accommodation in Boston: we stayed at Howard Johnson Inn Fenway Park Boston, a small hotel a few steps away from the Fenway Park stadium, home to the Red Sox.
  • Transportation: buy your Charlie Card to get around the Boston area. Although the city can be easily explored by foot, we got ours after dropping off our rental car at the Logan international airport in order to reach our hotel in Fenway Park.

I hope you liked Boston, I certainly did! Have you visited this American city already? What did you think? Please leave a comment below.

Interested in more of our summer road trip adventures? Read about all of our stops below: