Boston Travel Guide: Best Things to Do and Eat

Recently, our new friends from France, who were planning a trip to Boston, asked for some recommendations as to things to see and do in the city. After writing back to them a ridiculously long email with bullet points and footnotes of my favorite Boston sights and restaurants, I decided this comprehensive list was too good not to share it with you all! So, here we go!

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Where to Stay

For the 10 years we lived here, we have moved around quite a bit, from a duplex in Brookline to a brownstone in Kenmore Square. When we visit Boston, we prefer to stay near the Back Bay just because it’s so central with easy access to the different lines on Boston’s subway (known as “the T”). Our friends with kids like to stay in a vacation rental because there’s more space and oftentimes a kitchen and laundry. Whatever your preference, just know that there are a lot of options!

Best Things to Do

(1) Walk the different neighborhoods in Boston

Boston is a very walkable city, so if you have the time, definitely see the city by foot. It doesn’t matter whether it’s spring, summer, fall, or winter, Boston is always beautiful. For an overall appreciation of the the city and a good starting point, walk the Freedom Trail with a local guide or on your own.

Boston Neighborhoods Worth Seeing:

BEACON HILL: this beautiful neighborhood takes you back to the 17th century, gas lamps, brick sidewalks, Federal style houses, and all.

BACK BAY / DOWNTOWN: home to the Boston Public Gardens, swan boats, shopping, and nightlife. I love walking down Beacon Street or Marlborough Street between Kenmore Square and the gardens. Simply breathtaking…

NORTH END: the little Italy of Boston. When the weather is nice, grab a cannoli or two or three and find a spot on one of the benches or tables in North End Park. Or do a food walking tour if you want to try some local eats while you explore.

SOUTH END: an adorable and somewhat newer neighborhood of the city with plenty of good eats and drinks.

FENWAY: Red Sox and Fenway Stadium.

CHARLESTOWN: a hidden gem with tons of history. Visit the U.S.S. Constitution and climb the 294 steps to the top of the Bunker Hill Monument.

HARVARD SQUARE: Technically not in Boston. But, it’s on my list because Harvard is Harvard. They also have a walking tour of the Harvard campus.

(2) Take the famous Duck Tour

If walking isn’t your jam, take a Duck Tour to see Boston by land and by water. Yes, it’s a bit touristy, but it’s a must do at least once when you visit Boston. Or you can also take a bike tour to get your bearings if you want to take it up a notch.

(3) Visit one of many incredible museums in Boston

My all time favorite museum is the Isabella Stewart Gardner Museum and ICA. If you’re an art history aficionado, then try the Museum of Fine Arts. If you’re an American history buff, you’ll love the USS Constitution Museum and the Boston Tea Party Ships & Museum. If you have kids, check out the Science Museum and the Boston Children’s Museum. Love penguins? Check out the New England Aquarium. There’s so many different places to discover!

(3) Take a peek into the Boston Public Library

The Boston Public Library is in the heart of Boston right across from Copley Square and steps from Newbury Street (shopping and restaurant street). It’s a beautiful and historical space that’s worth checking out.

(4) Go shopping on Newbury Street

The most popular street for retail therapy is Newbury Street, but all of the Back Bay has plenty of boutiques and malls to fuel your shopping needs. Check out Restoration Hardware’s flagship store on Newbury Street. Four floors of furniture displayed in what used to be the Museum of Natural History. Stunning all around. And when you need a snack break, there are tons of restaurants and dessert options nearby.

(5) Have a picnic and watch the sunset on the Charles River

And when you’re tired from all of that exploring, pack a picnic or grab food nearby and watch the sunset from the Esplanade (check out the best places for sunsets in Boston).

(6) Sail the Boston Harbor

If you want to get out on the water, take a sail boat or sunset cruise from the Boston harbor. You get to enjoy a new perspective of the city.

(7) Do a tour of Fenway Stadium

If you’re a baseball fan, take a tour of Fenway Stadium. I don’t love baseball but joined a tour when my cousin came to visit one summer and it was fantastic. I learned a lot of interesting facts and got to see the stadium from different viewpoints that I’ve never had the opportunity to see when going to a game or attending an event there.

Where to Eat

Toro: Amazing and inventive tapas. Tasty drinks. Fun atmosphere. Long lines, so get there early. 

James Hook & Company: When in Boston, eat seafood. Delicious and most reasonably priced lobster rolls, chowders, and other seafood items. Not a sit down restaurant, but there’s outdoor picnic table seating with a waterfront view. For those driving, there’s space for parking.

Legal Seafood: Boston seafood institution. There are multiple locations that all have a different twist to their menu. Everything is fresh and the service is great.

Giacomo’s: Hearty homemade Italian goodness in the North End Giacomo’s (no reservations). Try the mussels in garlic white wine sauce, the scallops with linguine, the butternut squash ravioli, well… try everything!

Futado Udon: Delicious creative udon. Near the St. Mary’s T stop by the Boston University Campus.

Tora Japanese: A yummy find for those who like raw fish. A small space in Chinatown where you can customize and make your own sashimi bowls.

Tatte: Great place for breakfast or lunch. A cafe with delightful pastries, sandwiches, salads and desserts in a beautiful space.

Saltie Girl: If you want to have a girl’s brunch or are celebrating a special occasion, try this chic seafood spot.

Ernesto’s Pizza: Good ol’ affordable pizza from plain cheese to eggplant ricotta to hamburger sausage. All delicious!

That’s all folks! Hope you enjoy everything that Boston has to offer! More questions? Just ask in the comments below!

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4 responses to “Boston Travel Guide: Best Things to Do and Eat”

  1. darwinontherocks Avatar

    Thank you for these recommendations !

    1. oliveolove Avatar

      Your welcome! Hope you can visit Boston soon!

      1. darwinontherocks Avatar

        I wanted to do it last year, but taking the train from NY to Boston was a bit too much for our budget. Maybe next time !

  2. […] of favorite Boston sunset viewing spots. Also, if you’re planning a trip here, check out my Boston Travel Guide for places to stay, best things to do and our favorite […]

I’m Tiffany

Hi! I’m a working mama who loves to travel and explore new places with her family. I hope you find some adventure tips, guides and inspiration to help you plan your next family trip! It’s so great to have you here! Live and love!

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