Two Days in Boston, Massachusetts

Boston is the biggest little city that is full of culture, history, food, and fun! While you could spend a lot of time here exploring, we only had two days in Boston and packed in as much as we could. While visiting one of my friends who lives in the Berkshires, we decided to spend a night in Boston and pack in as much as we could in two days.

We stayed at the newly opened Yotel Boston, and it was great! Fair warning: The rooms are small. But if you just need a nice room to sleep in, this is a great option. The hotel, or should I say Yotel, is very trendy and modern. The hotel rooms are actually called cabins, and it really reminded us of a cruise ship cabin! It is located in the Seaport neighborhood and right next door to a T stop.

Two Days in Boston

Day One

Duck Tour: If you don’t have a lot of time in Boston, the Duck Tour is the best way to to see as much as possible in a short amount of time. The guides all have great personalities and add some fun to the tour. Your tour duck also goes into the water, so you get to see Boston from the Charles River! The only downside is you don’t actually get to walk around and explore these areas, but this gives you a great overview of the neighborhoods and landmarks around the city. There are three departure areas throughout Boston.

Dinner in the Seaport area: Since our hotel is located in the Seaport neighborhood, we decided to walk to a restaurant nearby. This is a really fun area with plenty of bars and restaurants to choose from. Legal Seafood has a great rooftop bar! Read more on the Seaport neighborhood here.

Day Two

Fenway Park TourTake a one hour walking tour of America’s oldest baseball stadium! This is a great, quick way to see Fenway Park and learn more about the history of the park at the Red Sox. Unfortunately the Red Sox were away while we were there, so we couldn’t see a game! For more information on the tour, check out their website.

Freedom Trail: Of course the Freedom Trail has to be on this list! This is definitely worth experiencing. The Freedom Trail is a 2.5 mile walking route that takes you to important historical sites throughout Boston. You can see some of the most famous historical sites from the American Revolution, like the Old North Church and the site of the Boston Massacre. There is tons to see and learn throughout the trail. Even if you don’t want to walk the entire 2.5 miles, you can hop on the trail when you see the ride line in the sidewalk. You will end up somewhere interesting. You can take guided tours or just walk it yourself. There is tons of free information available. Some of the sites you do have to pay a small amount to actually go in. We definitely recommend checking out the Old North Church (optional donation). Everyone learned about “One if by land, two if by sea” in school, and it was a really great experience to see where this happened in person. You can even sit in the pews and hear a talk about the history of the church and it’s important place in history. Fanueil Hall/Quincy Market is definitely a happening part of town. There are shops, restaurants, and street performers, which make it a great spot to relax and people watch. Learn all about the Freedom Trail here.

Other Things To Do

There is SO much more to do, but if you just have two days in Boston, these are definitely the highlights you want to hit. We definitely want to go back and spend more time!

Here are some more things to do in Boston:

Boston Commons

Boston Public Gardens

Boston Symphony Orchestra

Boston Pops

Rose Fitzgerald Kennedy Greenway

New England Aquarium


New England Holocaust Memorial

Samuel Adams Brewery

Swan boats

Whale watching cruise

Spirit of Boston Dinner Cruise


The North End

Obviously there is a lot to do here, but this is a great way to spend two days in Boston. It is a small city with a lot of history, culture, great food, and great sports! 

What are you favorite things to do in Boston? Let us know in the comments!

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