How to spend a weekend in Boston

Visit Boston in 2 days | what you SHOULD SEE

Curious about how to spend 2 days in Boston? Where to eat? What to do and what to see?

I’ve spent 4 months in Canada and during that time I practically lived at the US border, so it was a no-brainer to at least cross the border once! The choice was quickly made for Boston!

Together with 2 friends, I picked a place and a date: Boston, the beginning of December. Not the most popular time, but pretty good for a weekend.

We ended up booking a flight from Toronto to Boston through Porter Airlines. We found this cheap deal on Expedia: hotel + flights for 350 CAD each! This was the cheapest deal to find at the moment.

Through my story, I will explain to you all the do’s and don’ts for spending a 2 days in Boston in winter, as well as where we stayed (why I loved our hotel) and everything you can visit on a weekend!

Where to stay

First, we tried to look at the available Airbnbs since they are, most of the time, the cheapest option (after hostels). Unfortunately, this was waaay more expensive than we expected!

An Airbnb in Boston is as expensive as a four-star hotel! WHUT?!

So that’s when we decided to look for a hotel instead. If you could have more luxury for the same price, why not!

This lead us to booking a double room at the Boston Park Plaza!

The arrival

A flight through Porter Airlines was the cheapest option, but it was definitely not the fastest.

On our way to Boston, the flight had more than an hour delay because of a snowstorm that was coming over Boston.

On the way back the flight had also more than an hour delay, for a reason I still don’t know.

But eventually, we got there!

Do I recommend flying with Porter? Meh, not exaclty.

Boston Park Plaza

Boston Park Plaza
Boston Park Plaza

After a flight that took way longer than expected, we were incredibly happy to finally arrive at the Boston Park Plaza!

However, when entering the building we suddenly realized we were totally underdressed…

That night, a gala was taking place (by a private organisation) so everyone in the hotel looked impecable! Except for us…

We were coming in there with our snow jackets, snow boots and just a backpack to avoid extra fees for the flight (read this post for more tips about saving money with low-cost airlines). In short, we were looking completely bewildered!

This is why I felt a bit awkward at first, but the staff was very friendly and helpful and eventually, we weren’t the only underdressed people arriving!

Anyway, the hotel turned out to be a perfect choice! It was recently renovated and looked amazing! However, keep in mind that people are generally well-dressed there ;).

Boston Park Plaza maquette
Boston Park Plaza maquette

In general, the hotel was very clean and the hotel had all the stuff available to make it a wonderful stay!

The Boston Park Plaza is located next to the Boston Public Garden and couldn’t be more centrally located in the city. From there you can go anywhere on foot or by taking the metro.

So I recommend booking a hotel/bnb/whatever around the Boston Public Garden since it is the most centrally located place you can get!

What to visit in Boston in 2 days

Boston Public Garden

Boston Public Garden
Boston Public Garden

Besides it being the perfect location to book a hotel, it is a beautiful park to go for a walk. There are actually two parks next to each other: Boston Public Garden and Boston Common.

A walk through the park looks insanely beautiful in winter! (That’s what you probably can see form the picture.) Lights are hung up and all trees surrounding the parks have different colours.

Moreover, in winter, they have an ice rink, which is definitely recommended if you are looking for a fun activity! However, it is a quite popular rink so be prepared for a bit of a queue.


Cheers Bar Boston

Cheers was a very popular series that took place in Boston. In the building that figured as the entrance to the fictional pub, there is currently a pub that is still open for the public! Many fans are visiting the place every day, so if you’re a fan, go visit it!

You can eat something inside, but I would not go in there without a reservation!


MIT building

Who doesn’t know the Massachusetts Institute of Technology, or shorter, MIT!

As a student it was a must for me to see that place. You can just walk around campus and because it was exam period we could even go inside the building and just visit the classrooms!

How amazing is that!?

The MIT sign - Boston in 2 days
The MIT sign


Harvard gate - weekend in Boston
Harvard gate

Even more famous than MIT is Harvard, and accidentally or not, they are located not too far from each other!

When we booked our 2 days in Boston I knew that Harvard was a must-see for me and honestly, it looks amazing.

The whole neighbourhood is built around Harvard and remarkably cozier than the rest of Boston.

What you absolutely should start with is a walk around campus. Soak up the atmosphere and enjoy the pretty buildings and students walking around!

We tried to go into some buildings but unfortunately, they are only accessible by students at Harvard. You can try anyway if you want ;), the only problem is that the security figures out fairly quickly that you don’t belong there.

Harvard Art Museum

Harvard Art Museum
Harvard Art Museum

There is a lot to see at Harvard and one of those things is the Harvard Art Museum. If you love museums and art and you have some spare time on your 2 days in Boston, what are you waiting for?

Harvard Book Store

Harvard Book Store
Harvard Book Store

I love bookstores and certainly bookstores at Harvard! Besides books about all scientific subjects you can image, you can find postcards and souvenirs here!

Harvard Coop

Harvard Coop
Harvard Coop

Another bookstore at Harvard is Harvard Coop, here you can find all novels you can imagine! So no scientific books this time but romans and thrillers!

Trinity Church

Trinity Church - Boston in 2 days
Trinity Church

Trinity Church is centrally located in Boston and a beautiful church to visit. People who read my posts about Toronto and Montréal will know that I love to visit any church I encounter on a city trip simply because I love the serenity and architecture of churches!

And it is not different for this church! If you love to find some peace, get in there!

Boston Public Library

Boston Public Library - Boston in 2 days
Boston Public Library

The Boston Public Library is located right in front of the Trinity Church. We planned to visit the library but unfortunately, it was closed the moment we got there. From the little bit of the income hall we’ve seen I can tell you that it must look amazing on the inside!

Definitely a spot to visit on when you spend 2 days in Boston! (Just make sure you check the opening hours.)

China Town

China Town - Boston in 2 days
China Town

All large cities have a China Town and Boston is no exception. I love to soak up the atmosphere there and taste some of the best Asian food!

I had my first bubble tea at Boston’s China Town! (To be honest, it’s not my favourite drink…) It was a fun experience but I still don’t get the concept though.

We also found an amazing Vietnamese restaurant which was cheaply priced but really popular in the neighbourhood! More about that below in the section ‘where to eat’.

Church of Christian Science

Church of Christian Science outside Boston
Church of Christian Science

To be honest, the name sounds a bit creepy somehow but it is a church you cannot miss!

At the time we visited Boston, the church was being renovated on the outside but you can easily imagine how beautiful it must look underneath the covers!

On the inside, the church looks like a big theatre. It has 2 floors and the guides will fight to give you the best explanation of the building and the church movement!

For the record: the visit is completely free!

Church of Christian Science inside Boston
Church of Christian Science inside

The Mapparium

The Mapparium is located in the Marry Baker Eddy Library and next to the Church of Christian Science.

It is basically a giant ball with the world projected on the inside of it. It’s all made in glass and the acoustic is quite remarkable!

You’re not allowed to take photos inside so unfortunately, I don’t have any pictures of the inside for you. However, it is a must-see! This was one of my favourite visits and you will be astonished by the beauty of this map!

The entrance fee is only 6 dollars for adults and 4 for students. The visit only takes half an hour so it is perfect for a quick stop! Entrance to the library is free.

Quincy Market

Quincy Market Boston in 2 days
Quince Market

Quincy Market is an indoor market in Boston full of little food and craft booths. It is extremely cozy to walk in and you even have a cheers-bar and a cheers-souvenir shop!

If you’re looking for tasty food, candy, paintings, other crafts or just a nice atmosphere you should stop here!

Quincy Market candy
Quince Market

Little Italy

Spending 2 days in Boston would not have succeeded without seeing Little Italy! It is a region full of Italian restaurants and wine bars. So if you’re looking for a good game place to eat, this is the place to be!

Inside Mike's Pastry
Mike’s Pastry

When you’re walking through Little Italy you definitely have to stop at one of the bakeries where they have lovely pastry! Bova’s Bakery or Mike’s Pastry are excellent choices!

The Waterfront

Charles River Boston in 2 days
Charles River

There is a lot of water surrounding Boston and taking a walk along the waterfront gives you an amazing view!

You will see that walking along the river Charles is a popular activity for those who live in Boston. If you’re walking at the side of Boston center, you can see MIT lying across the river!

Another option is to go through Little Italy and take a look at the harbour-side of Boston, also definitely recommended!

King’s Chapel

Park Street Church Boston in 2 days
Park Street Church

This cute little church is located next to Boston Common and has a very long history dating back to the foundation of the USA. In the church, you can read about the history of the church relating to Boston and how people used to regard and interact with it.

It’s a beautiful place to visit and if you could only pick one church to visit on your weekend in Boston, it should be this one!

They also offer tours and entrance is free, however, they expect you to give a small gift to the church.

Freedom Trail

The Freedom Trail is simply a route you can walk that will take you to all the major sightseeing attractions of Boston. So if you really don’t know what to do or you don’t want to figure it out, you can always opt for this route!

(It can even be found on Google maps!)

Go shopping!

Downtown Crossing Boston in 2 days
Downtown Crossing

Some people simply don’t like the all the cultural stuff just like one of my friends who joined me on this trip. So, that’s when she took us shopping in Boston!

We went to Downtown Crossing, an area with lots of large shops and shopping centers. Thus, if you feel like shopping, you need to go there!

Where to eat

This one is for the food-lovers out there!


The Boston Park Plaza offers breakfast for an extra cost but since we wanted to discover as much of Boston as possible we decided to take breakfast outside the hotel!

Pret A Manger

For a cheap but decent breakfast, we went to ‘prêt a manger’. This is a breakfast/lunch chain that offers a not-to-bad breakfast for a decent price.

Tatte Bakery & Cafe

Tatte Bakery & Cafe Boston
Tatte Bakery & Cafe

One place we absolutely had to try for breakfast was Tatte Bakery & Cafe. This insanely popular bakery is completely french-style. The best pastry and croissants are found here! This is definitely a place I recommend for having breakfast!

The only thing you have to watch is the timing. On Sunday morning this place will be full and there will be a row standing outside! You can check on Google when Tatte will be the calmest.


Caffe Vittoria

In this cozy cafe in Little Italy, you can get all kinds of pastry and coffees. It’s a very nice place to have a rest if you are walking through the neighbourhood or having a look at the waterfront.

The decor on the inside looks very authentic and it’s a pleasure to stop by and have a drink there!

Other options are the bakeries I talked about in Little Italy, definitely worth a stop!


Maggiano’s Little Italy

Our first night we had dinner at Maggiano’s Little Italy. This is an Italian-like restaurant at Statler Park. The restaurant aims to create an Italian atmosphere but honestly, when you come from Europe, you only see Americans imitating Italians.

Nevertheless, it is quite cozy and you get huge amounts of meat! The restaurant is not cheap but when you visit Boston you’ll have to live with the fact that the city in general is not cheap.

However, if you really want to eat Italian food I recommend to go to Little Italy instead!

Pho Pasteur

This Vietnamese restaurant is located in China Town and one of the most popular dining establishments in the neighbourhood! Their food is simply phenomenal and their prices very cheap for the quality they offer!

I really recommend you make a reservation if you want to eat here because it can be quite busy. When we went to eat there we didn’t make a reservation and had to queue 10 minutes until there was a free table.

Are you ready to discover Boston?

I hope I provided you with enough inspiration to go discover Boston yourself!

There is so much to do in the city that you can easily spend more than just a 2 days in Boston! But I know you don’t have forever.

Therefore, I suggest taking the subway as much as possible to save time and to visit the highlights like Harvard, the Freedom Trail, Little Italy and China Town!

Just a quick note about the weather. We visited Boston in winter. It was snowy, icy and foremost windy. So if you’re planning on visiting Boston in winter, be prepared for the cold!

Let me know if you have any other advice or if you have been to Boston and feel like I’ve forgotten something essential!

Still not sure which city to visit on your city trip? Read about my city trips in East-Canada!

How to spend a weekend in Boston

11 thoughts on “Visit Boston in 2 days | what you SHOULD SEE”

  1. This is awesome. I love visiting anywhere when it’s around Christmas time. The decorations and time of year make me so happy!

  2. A very nice and informative post… Can’t wait until this COVID this is over so I can go back out there and travel.. thanks for sharing these tips

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