8 of the Best Things to do in Boston, Massachusetts

Are you looking for things to do in Boston, Massachusetts? I’ve put together a list of all the best things to do to make sure you have an incredible vacation!

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There are so many great things to do in Boston, Massachusetts!

I just recently went to Boston for the very first time, and I completely fell in love. I truly wasn’t expecting to love it as much as I did.

I really wanted to go somewhere I hadn’t been – and as a lover of a beautiful city, ocean views, and plenty of fresh seafood – Boston, Massachusetts seemed like a must-see!

Honestly, Boston ended up being one of the best trips I’ve ever taken! Here are some of the best things to do in Boston, Massachusetts so maybe you’ll love it as much as I did!

This post is all about the best things to do in Boston, Massachusetts!

Best things to do in Boston, Massachusetts!

1.) Freedom Trail

A great way to kick off your time in Boston, Massachusetts is by walking the Freedom Trail. The Freedom Trail is a great way to learn a little history about Boston while you’re also starting to get your bearings in the city. I always find when you’re visiting a new city it’s great to do some sort of tour – whether by walking or by bus – to help you learn the layout and plan your future stops for the rest of the trip.

The Freedom Trail is essentially a two-and-a-half-mile trail that winds through several historic sites in Boston. The best part about it is that it’s literally just a line painted throughout the city – so you can follow the trail yourself, at your own pace, and start at whatever point you want.

You’ll see sights like Boston Common, Paul Revere’s House, Faneuil Hall, the USS Constitution, and so much more! Definitely carve out time for this experience, if your schedule allows, do it near the beginning of your trip!

2.) Faneuil Hall

One of the places you’ll see along the Freedom Trail is Faneuil Hall. Faneuil Hall is a huge marketplace right in downtown Boston. There are so many cute little shops and some amazing food! If you want to try several different foods among your whole group is a great place to go because there are so many grab-and-go quick options!

Stop by the Quincy Market Collonade, located right in the middle of Faneuil Hall, for some of my personal favorite spots and for some casual seating to enjoy all your lunch, dinner, or snacks! Faneuil Hall is definitely one of the best things to do in Boston, Massachusetts!

3.) Go Whale Watching

One of my all-time favorite things we did while in Boston was go whale watching. I had been whale watching one other time in Hawaii.

If you really want to go on a whale-watching tour while in Boston, Massachusetts make sure you go during peak season! The whales are usually more prevalent from mid-March through November.

We saw a whale they named “Snap.” We saw him several times flipping his tail out of the water and he came up and swam right by the boat at one point.

If you do this tour plan on being out on the water for a long time! The tour starts with at least one hour of travel time out to where the whale sanctuary is, then you spend a couple of hours searching and watching the whales you find, then, of course, you have at least an hour back.

Other things to note:

1.) Get there early! We got there an hour before the boat took off and we still weren’t the first people in line. By the time it was 30 to 15 minutes before the tour, the line was MASSIVE. If you don’t mind where you sit you will still be able to get a seat, but if you want the best views, I would suggest getting there an hour early. The weather was perfect for us so we opted to sit outside on the very top deck. If your weather is pretty good, top deck is the way to go. You can get views from every single angle of the boat. There are front and rear decks too though that all have good views! There were plenty of open seats on the inside part of the boat throughout the whole tour. If you’d rather be away from the wind and sun that could be the best option for you. It’s surrounded by windows, but you can always go outside and stand by the rails when a whale is being spotted.

2.) They serve food and drinks on the boat! There were lots of snacks – chips, candy, hotdogs, etc. Then they had soft drinks and alcoholic beverages for purchase as well!

3.) “New England Aquarium” in Boston

The Boston Aquarium, named the “New England Aquarium” is a great thing to do right after your whale-watching tour. The place you board for your whale tour is located literally just steps from the entrance of the aquarium. If you purchase tickets online they offer joint tickets to do both on the same day for a little bit of a discount.

Be warned, the aquarium is VERY small compared to other aquariums I’ve been to, but they still had a couple really cool things. The penguin exhibit is open-air, and I’ve only ever seen penguins behind glass. We were there at the time of the penguin feeding, so it was cool to see their whole presentation and watch the process of the feeding.

Another part I loved was the stingray tank. We stayed for quite a while petting sting rays!

4.) Isabella Stewart Gardner Museum

The Isabella Stewart Gardner is absolutely stunning. When I heard about it, I knew I wanted to visit on my trip to Boston.

Isabella Stewart Gardner started building the museum in the 1800s. It has several floors and rooms packed with amazing artwork. Located in the middle of the museum is a stunning courtyard garden. Although you cannot walk through it, all floors have doors that open up to it to provide a beautiful view and great photo op. The ground floor has several good viewing spots as well!

In my opinion, one of the most interesting things about the museum is “the theft.” In 1990 13 pieces of art were stolen from the Museum – making it the largest property theft in the world. When you walk through the museum you can still see the empty frames left behind that once held the historic paintings.

Before our trip, I watched “This is a Robbery: The World’s Biggest Art Heist” ( I was able to watch it on Netflix) which details the whole crime. I highly recommend watching it before you go, it makes the whole experience even cooler knowing the whole history behind the empty frames.

5.) Fenway Park

Even if you’re not a big baseball fan Fenway Park is worth checking out! It’s walking distance from the Gardner Museum, so if you’re already in the area you can stop by! Check out a baseball game if you are there on a game day – or sign up for a guided tour if it’s an off day!

6.) Eat, Eat, Eat!

If you know me, you know I LOVE seafood – and Boston has no shortage of it! There are so many staple food items you have to eat while in Boston: Oysters, Lobster Rolls, Clam Chowder, Cannolis, and Boston Creme Pie.

Two of my favorite places we ate were Neptune Oyster and Union Oyster House.

Neptune Oyster is VERY small. There is almost always a line and it’s very crowded – so be warned you’ll kinda be squeezing in. But the food was so amazing. They had a huge range of different types of oysters, and the best part was you could mix and match at whatever amount you wanted. You don’t have to order by the half dozen or dozen.

At Neptune, we got two of each oyster they offered. I ordered the octopus and Daniel ordered the lobster roll. Everything was incredible – including the service! Just crowded 🙂

Union Oyster House is another staple item in Boston restaurants. Apparently it is the oldest restaurant in America. It is also located along the Freedom Trail, so if you need some food along your 2-and-a-half-mile hike, this is a good stopping point!

Once again, the service here was amazing. We didn’t have to wait at all with no reservations. We had a dozen oysters, and some clam chowder, and both of us opted for the Lobster pot. We got the medium lobster and got it boiled. It was DELICIOUS! I scarfed my down so quickly.

As far as desserts, there are so many great places to go – but my top recommendation is of course Mike’s Pastry! We both got cannolis – I got the chocolate chip cannoli and Daniel got the chocolate mousse cannoli.

There are SO many great food options in Boston that it can get a little overwhelming. So if you’re having any trouble deciding where to go look up some Boston food tours! There are so many to choose from and they allow you to see some of Boston’s hotspots and try a little bit of something at each one.

7.) Stroll Through Harvard Square

Harvard Square is a little plaza with tons to do in and around the surrounding area – obviously located by Harvard University. There are hotels, restaurants, bars, and tons of shops! It’s a beautiful little area and a great way to spend some downtime exploring food and retail!

8.) Explore Some of My Favorite Neighborhoods: Back Bay and the North End

If you’re an ocean lover, Back Bay is the place to be. It’s technically just a neighborhood of Boston that winds side by side with the water. There are plenty of shops and restaurants you can eat at with a stunning view of the water the whole time.

Also, check out the North End! I mentioned Mike’s Pastry earlier, which is located in this neighborhood. There are so many great restaurants, specifically Italian restaurants, that are WELL worth checking out!