We visited Boston, Massachusetts in July of 2019 for our family summer vacation. We had such a great time exploring an amazing city and eating all the Lobster rolls we could find! We booked our hotel stay with the Hyatt Regency Boston, located in the heart of Downtown. We walked to numerous different places on the list below, but rented a car to drive to Harvard/Cambridge area and when we visited Cape Code/Nantucket and Rhode Island. (Another state, another post!) If we hadn’t done those two day trips, I don’t think a car would be necessary.

Disclaimer: We visited Boston in 2019, so make sure to check hours and openings for everything I’ve listed in this post,
as many might have changed.

Boston is FULL of things to do, but I tried to stay true to things that are UNIQUELY BOSTON.

Boston Commons and Public Garden
These two are adjacent with just a street in between them, so I’m putting it into one. I’d describe it as the “Central Park” of Boston. Great people watching, place to bring a ball to throw and/or kick around, fly a kite, have a picnic, and don’t forget to ride the swam boats! There were a few small street vendors set up as well and small snack stands. *This is where the Freedom Trail begins. Nearby is the Beacon Hill Neighborhood area, where we walked around one day to snap a pictures on the famous Acorn Street.

Freedom Trail
An absolute must! The history in Boston amazing and this is your one-stop-shop for a majority of it! The Freedom Trail is a literal brick trail that goes throughout a large part of the city. I shouted “follow the brick line!” about 15 times and the kids loved finding it whenever we’d come back out from a building. I’d describe it like a treasure hunt, following the brick line to the ‘X! marks the spot’! We did a self-guided tour using the Freedom Trail App, so we could go at our own pace with the kids, but guided tours are offered all over! We even stopped a few times next to one to hear some of the tour guide’s information. (Tour crashers) It’s a full day of walking, so bring a stroller for the littles. We ended the tour at the Boston Harbor shipyard where we toured the USS Constitution, a wooden ship commissioned in 1794! Ubering to your next destination or to your hotel would also be a great option, especially with kids. We walked back to Little Italy for dinner, which seemed to be the halfway point, then Ubered to the hotel from there.

North End / Little Italy
This area was all about the eats for us. We stopped and got cannoli’s during the Freedom Trail, then ended back there for dinner at Carmelitas. Then made it back a 3rd time for pizza Regina Pizzeria (locations all over Boston) one evening. Seriously, everything we ate here was incredible. Back to the cannoli’s for a second. There’s an apparent Cannoli War between two pastry shops, Mike’s Pastry and Modern Pastry. It was a featured on one of Food Network shows! They are right down the street from each other, so I get the competitive vibes! Another favorite was Cafe Vittoria for a good ol’ fashion Italian coffee.

Faneuil Hall Marketplace
Food hall with shops now, but served as a meeting place for Patriots on the eve of the American Revolution! It was super busy when we went, so I wouldn’t recommend going on Saturday afternoon, if you can. We didn’t even end up going inside because it was shoulder to shoulder crowds. That’s a NO from me, with a stroller and four kids. This was actually our very first stop after getting off the plane in Boston. We miraculously found an outside table (not too hot outside for these Floridians) and ate some New England Clam Chowder at Salty Dog! After watching some entertaining street performers, we walked to The Holocaust Memorial nearby, which was super cool!

Whale Watching Boat Tour with Boston Harbor Cruises
This was a little like fishing and involved a lot of waiting around. The tour lady even joked that it should be called “Whale waiting, not watching”. I had high expectations and maybe I was picturing huge whales jumping up right in front of us, ya know, like SeaWorld. LOL I don’t want to dissuade anyone from doing an experience like this, because we really enjoyed ourselves, and did get to see a few whales up close and personal. If you do an experience like this, pack wind breaker type jackets. It was crazy windy and even a little chilly. The boat does have an inside sitting area, but I don’t see the point of whale watching if you don’t whale watch. The outside is where all the action is. Tip: Put your name on the list at Legal Seafood before boarding the boat, for lunch or dinner after Whale Watching.

Fenway Park
Catch a Sox game or tour Fenway Park! Then, eat or grab a beer at Bleacher Bar. It’s under the Fenway bleachers and looks out into field.

We drove over on a late afternoon to walk around and explore the Harvard campus, just because it’s HARVARD. We shopped in some of the book/school stores and ate dinner at the famous burger place called Mr Brantley’s. (Cash only). If you are in this area earlier in the day, visit Arnold Arboretum, an outside museum displaying over 15,000 woody plants and offering educational programs for people of all ages.

Copley Square + Prudential Center
We spent one afternoon exploring this area, which is full of beautiful buildings, high-end restaurants and shops. We saw the Boston Marathon Bombing Memorial, Trinity Church, bought a soccer ball in a sports shop we stumbled upon, and ended up at the Prudential Center to do the Skywalk (which I heard is currently closed, but worth it to check out). The Skywalk had the best views of the city and fun interactive games for the kids.

Isabella Stewart Gardner Museum
Famed for being home of one of the biggest unsolved art heists in America!

Boston Tea Party Ships and Museum

Samuel Adams Boston Brewery Tour

Community Boating Boston
Rent a kayak, paddleboard, or sailboat

Boston Public Library

The Mapparium at Mary Baker Eddy Library

It was so hard NOT to eat a Lobster Roll everywhere we went

\\ North End Little Italy //
Modern Pastry
Mike’s Pastry
Al Dente 
Regina Pizzeria

\\ Fenway //
Neighborhood Coffee + Crepes (Duh, get a crepe!)
Bleacher Bar (Looks out onto Fenway field)

\\ Central/Downtown //
Union oyster house (“Oldest restaurant in America”) 
The Barking Crab (By the Tea Party ships)
Saltie Girl (Lobster + Waffles)
Tatte Bakery (Get the Avocado Toast and their pastries)
Union Square Donuts (Boston Crème + Brown Butter Hazelnut Crunch!)
Rinos Place (Get the Lobster ravioli) 

\\ Cambridge Area //
Mr Brantley’s (On Harvard campus) cash only
Bagelsauras (Hot Smoked Bagel or TRex)