2 Days in Boston – Weekend in Boston Itinerary

Newbury Street, Boylston Street, 2 Days in Boston (12 of 19)

The City of Boston is filled with so much history, stunning architecture, culture, and uniqueness which will surely amaze you.

I visited Boston not expecting to be too impressed but I was pleasantly surprised how much I loved the city. Because I had such a fantastic time on our weekend trip, Boston became one of my favourite cities in the USA.

My love for the city is what spurred me to create the ultimate 2 days in Boston itinerary. My itinerary consists of a map including destinations such as restaurants, historical sites, parks and much more.

So keep reading to get the perfect two-day experience in Boston!

Note: We did a LOT of walking so make sure to bring some comfy shoes if you’re following this itinerary. The only area we did not walk to was the Sam Adams Brewery Tour.

Map of Boston Tourist Attractions

The map includes two different layers: layer one is day #1 in Boston and layer two is day #2. The red stars and lines drawn indicate the official Freedom Trail and all the sites.

2 Days in Boston – Day 1

Breakfast at The Thinking Cup

Breakfast at The Thinking Cup, 2 Days in Boston (1 of 19)

We stumbled upon the perfect coffee shop while trying to find a breakfast spot. The Thinking Cup coffee shop is a fantastic place to eat and drink your morning cup of joe.

There are only three locations in the world but the one we found was right next to the start of the Freedom Trail.

Breakfast at The Thinking Cup, 2 Days in Boston (1 of 19)
Breakfast at The Thinking Cup

We loved the coffee shop so much we decided to eat here for two days straight. The coffee and food are delicious and a terrific spot to start your weekend in Boston.

Boston Public Gardens

Boston Public Gardens, 2 Days in Boston
Boston Public Gardens

Located right next to the start of the Freedom Trail, the Boston Public Gardens are not to be missed before your journey on the Freedom Trail.

Boston Public Gardens, 2 Days in Boston

Established in 1837, the garden is the first botanical garden in the United States. The garden maintains a Victorian elegance and has had swan boats for rent for over 100 years!

Start The Freedom Trail

Boston Freedom Trail, 2 Days in Boston

The Freedom Trail is the ultimate highlight of Boston. At 2.5 miles long, the trail shows the best parts of Boston and more. If you are planning only one day at Boston, this trail is a must.

The trail is filled with historical parks, churches, museums, burying grounds, a ship, historical houses, and so much more! You can experience the trail in several ways such as hiring a tour guide, do a self-walking tour, or even an audio tour.

I suggest taking all day to complete this trail because it is filled with so many great sites and history.

The Freedom Trail begins at the Boston Common and is known as America’s oldest public park in the United States. The Commons was my favourite park in Boston due to the shapely trees, the modern skyscrapers in the distance, and the colourful flowers.

The Massachusetts State House, 2 Days in Boston
The Massachusetts State House

After the Boston Common, the trail takes you through The Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, King’s Chapel Burying Ground, Benjamin Franklin Statue & Boston Latin School, Old Corner Book Store, Old South Meeting House, Old State House, and the Site of The Boston Massacre.

Old State House, 2 Days in Boston
Old State House

At some of the sites, you can tour inside but it costs USD10-USD20 per person.

Granary Burying Ground where Benjamin Franklin’s parents were buried, 2 Days in Boston
Granary Burying Ground where Benjamin Franklin’s parents were buried

Eat: Lunch at Quincy Market or Faneuil Hall Marketplace

Faneuil Hall Marketplace, Quincy Market, 2 Days in Boston (16 of 19)
Quincy Market or Faneuil Hall Marketplace

The Quincy Market is located on the freedom trail between the site of the Boston Massacre and Paul Revere’s house. The proper name of this area is actually called “Faneuil Hall Marketplace”, a name that the Boston Mayor Josiah Quincy requested.

But eventually, a sign “Quincy Market” was added to commemorate the mayor who helped create the market.

Quincy Market comprises of three buildings (Quincy Market, North Market, and South Market) filled with restaurants, shopping, and food stalls. The area is usually buzzing on weekends with tourists and locals trying to enjoy the day.

Pepper Palace in South Market, 2 Days in Boston
Pepper Palace in South Market

Tip: Make sure to visit the Pepper Palace in South Market if you love hot sauces like us. 

Finish The Freedom Trail

Old North Church, 2 Days in Boston (4 of 1)
Old North Church

After Lunch at Quincy Hall, we finished out the Freedom Trail at the Paul Revere House, Old North Church, Copp’s Hill Burying Ground, the USS Constitution, and Bunker Hill Monument.

Copp’s Hill Burying Ground, 2 Days in Boston (18 of 19)
Copp’s Hill Burying Ground

The last set of destinations only had a few sites in close proximity but there was still quite a few people walking around.

USS Constitution, 2 Days in Boston (19 of 19)
USS Constitution

The largest crown of people were trying to see the USS Constitution but the ship was surreal to see. You are able to see several decks of the ship and see how the sailors lived.

Copp’s Hill Burying Ground

Eat: Dinner at North End – Mamma Maria or Lucca

North End, Mamma Maria, 2 Days in Boston
Mamma Maria at North End

One of my favorite spots of Boston was the North End. Why?

Because the area has loads and loads of Italian restaurants and who doesn’t love Italian food?

We were lucky enough to grab a spot at the famous Lucca restaurant at the last minute and it was spectacular. Mama Maria is also a well-known Italian restaurant in the city.

2 Days in Boston – Day 2

Commonwealth Avenue Mall, Back Bay

Commonwealth Avenue Mall Park, Back Bay, 2 Days in Boston (3 of 7)
Commonwealth Avenue Mall Park

Established in 1856, Back Bay was a bay that would flood due to the Atlantic Ocean sending in waves to the Charles River. Eventually, a dam was built along with a new park called Commonwealth Avenue Mall.

The park is about 52 acres and is known for the beautiful uniform trees. The Park is a great place to take a stroll and take in all the greenery along with the surrounding Bostonian architecture.

Walk to Charles River Esplanade, Back Bay

Commonwealth Avenue Mall, Back Bay, 2 Days in Boston (13 of 19)
Charles River Esplanade

Esplanade Park runs 3 miles on the Boston shore adjacent to the Charles River. The park has plenty of views of the river, city, and several bridges. Many locals enjoy the scenery, running, kayaking, or even just taking a casual stroll. The park is a perfect spot to hang out and enjoy the day.

The Esplanade is also a great seasonal area to experience.

Spring days are filled with colourful, bright, cherry trees bursting into bloom.

The summer days bring in sunny days where people love to lounge around on the 5 floating docks and listen to music under the stars at The Hatch Shell.

Fall brings in bright orange and yellow foliage.

The park is the best spot to witness the colourful changes in the seasons.

Copley Square, Trinity Church and the Boston Public Gardens, Back Bay

Trinity Church, 2 Days in Boston (10 of 19)
Trinity Church

The Trinity Church and the Boston Public Library are located right next to each other. Both places are very interesting historical markers.

The old historical buildings with the modern tall skyscrapers in the backdrop, make for the best pictures.

Copley Square is an energetic area full of life and sunshine and all you need to do is take a seat at one of the benches to take in the beautiful crisp air.

Boston Public Library, 2 Days in Boston
Inside the Boston Public Library

My favourite part was the inside of the library. The architecture was stunning and the library was filled with countless works of art.

The library also holds about 29 million items (books, CDs, music, maps etc) and is the second largest public library in the United States. This library rivals with the likes of New York’s famous public library, so stopping by here is a must!

Eat & Shop: Newbury Street or Boylston Street, Back Bay

Newbury Street, Boylston Street, 2 Days in Boston (12 of 19)
Shopping on Newbury Street and Boylston Street

Newbury Street and Boylston Street are lined with trendy shops. It is a perfect destination for tourists and locals alike.

After the shopping is complete, make sure to grab some lunch at some chic spots. Some recommendations are Atlantic Fish Company, Back Bay Social, Mcgreevy’s, L’espalier, and Parish Cafe which is where we ended up eating at.

Sam Adams Brewery Tour

Sam Adams Brewery Tour, 2 Days in Boston

One of my favorite beers of all time are the Sam Adams seasonal beers. When I found out we were going to Boston, I made sure to pencil in the Sam Adams brewery tour. Located on the southwest side of town, the ride to this brewery was a bit longer than I expected, but, totally worth it.

Sam Adams Brewery Tour, 2 Days in Boston
Sam Adams Brewery Tour

The classical tours are first come, first serve and is free of charge. The tours run about every thirty minutes.

During the tour, you will to learn about the brewing process and the different types of ingredients they use to make the famous beer. The best part is the end when you can finally have the opportunity to taste of the different beers while they give some background on the beer and ingredients. In the end, you get to keep the glass tasting cup and the buzz from the tasting!

Looking at the schedule before the heading out is crucial. The brewery is a little far and the tours are only open during certain hours of the day.

Eat: Dinner at Union Oyster House or Emmets Irish Pub

Union Oyster House, 2 Days in Boston (7 of 7)
Union Oyster House

If you are a fan of oysters, lobster or in general seafood, then you HAVE to stop at Union Oyster House. The restaurant is located on the Freedom Trail and it is America’s oldest restaurant. They opened their doors in 1826 and has since been established as a National Historical Landmark.

The oysters were very fresh and savory, and the lobster was superb. If you are a history buff, experiencing the first ever restaurant in the USA is a must.

When I first started researching about Boston, I asked a local Bostonian to recommend some spots.

Emmets, irish, ireland, beer, 2 Days in Boston (2 of 7)
Emmets for a taste of Irish cuisine

One of the restaurants or pub she recommended to me was Emmets. I live in Texas, where there is no such thing as a real Irish pub, so I was sold right away on the idea.

Holy cow was she right!

The beers were cold and plentiful and the food was delicious. We had never tried Irish food before and we were pleasantly surprised. We ordered “The Taste of Ireland” and it was a perfect combination of their three most popular meals. The dish was savoury.


Boston is the perfect weekend summer getaway. It is filled with history, culture, beautiful architecture and a fantastic vibe. You might be surprised by how much you fall in love with the city. The city surely took me by surprise.

In case you want the best hotel deals in Boston, I got it covered. 😉



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Has any city ever surprised you, like Boston surprised me?


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Boston-Charleston-The Wandering Queen, 2 days in bostonMichelle Stelly lives in Dallas, Texas and is a full-time engineer. In her spare time, she loves to travel and her favourite destinations are National Parks. She blogs about her experiences and provides suggestions through her blog, The Wandering Queen. Michelle takes on her adventures with her husband Jameson and together, they travel the world, continually improving their photography skills. Follow Michelle Stelly to find out how a full-time professional can turn life into a fun adventure.

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