Boston, Massachusetts Travel Guide
Boston, Mass. Bean Town. Home to a boatload of American history (already starting in with the history puns), Boston is incredibly fun to explore. BONUS: It’s very walkable. I love walking around Boston, because it’s constantly buzzing with present-day activities … and then you’ll randomly happen upon a 300-year old graveyard and/or a very important location in American history. I don’t know about you, but it gives me chills to think I’ve walked along the same roads (even cobblestones) as some of the heroes of the American Revolution.
Although I cannot claim to know Boston like a local, George and I have family that DO (aka: my sister-in-law and her hubby, Liz & Tyler)! Fun fact: George and I actually met in Boston while staying at his older sister’s apartment. And, of course, we hit if off while sipping cocktails at a rooftop bar. Needless to say, Boston has a special place in our hearts.
We’ve put together a Boston travel guide to share all of our spots!
DO
Fenway Park. Fenway is home to the oldest baseball park in America. Bostonians are serious about their sports, so attending a sporting event is like a right of passage. Be sure to grab a beer at Bleacher Bar before heading into the park! Located on Lansdowne Street, this bar has a garage door that opens up to the baseball field where you can sip on your Sam Adams and watch the Sox take batting practice. PRO TIP: You can take food into the park (as long as it’s individually sized). We popped into Sal’s Pizza and grabbed a slice to-go to eat in the park because ball-park food a drinks are pricey.
Freedom Trail. The starting point is actually located in the Boston Commons! The trail itself runs a little less than 2.5 miles and circles the oldest parts of the city. It hits the historic sites like the Massachusets State House, Paul Revere’s House, The Old North Church, Granery Burial Ground and the Bunker Hill Monument. You can set up a tour or opt in to a Duck Boat Tour (touristy? yes. kinda cool? also yes).
Boston Commons. I’d say the Commons are to Boston what Central Park is to New York. BUT it’s actually the oldest public park in the USA. The Freedom Trail starts in the park and you can catch a glimpse of the Massachusets States house (just look for the giant golden dome).
Beacon Hill + Acorn Street. One of the oldest and most picturesque neighborhoods in the city. Acorn Street still has it’s original cobblestones, so be sure to mind your step. As one of the most photographed streets in America, we’d suggest going on a random weekday (we found it almost empty on a Thursday morning) and I’ve also read that Saturday morning are good for avoiding crowds (because everyone is sleeping off Friday night festivities).
Boston Harbor. You know. Where the tea was thrown overboard. You can visit the historic site and actually throw tea overboard! The Harborwalk extends for quite a while, so if you’re up for a stroll and looking at all the cute sailboats, this is your jam.
The North End. Home of Paul Revere, the Old North Church and a TON of authentic Italian food. Walk around and smell the fresh bread and garlic. And you must try a cannoli. A local’s tip? …“tourist sites will tell you [to try a cannoli at] Mike’s Pastry. But Modern Pastry is twice as good with half the line.” - My brother-in-law, certified Boston local.
Charles River Esplanade. A pedestrian’s walkway along the Charles River. Very chill.
Boston Public Library. America’s first public library! You can sign up for a tour to learn more about the building’s architecture (COVID may effect tours).
EAT
Carmelina’s. Liz and Tyler’s favorite place in the North End. Stellar Italian food and highly regarded on most every travel site for North End eats. We had reservations for dinner on a Thursday night and it was incredible. Make reservations ASAP because they book fast.
Fiore’s. Authentic Italian in the North End.
Mother Maria’s. Authentic Italian in the North End.
Modern Pastry. A local’s favorite cannoli spot! AND. AND. They actually have a bar downstairs where you can skip the line, order an espresso martini and have a cannoli (dine-in style). This is very little know so it makes for a good trick if you REALLY want a cannoli!
Bell in Hand Tavern. The oldest continuously operating brew pub in America.
Parish. Located close to the Boston Public Library, this would be a great spot for lunch!
Row 34. A great seafood option in the Seaport. In my opinion, best lobster roll in Boston.
Lolita’s. Best mexican option in boston. Fun (but dark) atmosphere with free cotton candy served as dessert at the end of your meal.
Contessa. This is a new spot in Back Bay on top of the Newbury hotel. Reservations are near impossible and prices are high, but if you are able to get in (even just sitting at the bar) it is worth it (wait staff is all in white tuxedos - very swanky)
Paramount. Great breakfast spot located on Charles street in Beacon Hill. Often a long line so visiting on a weekday would be recommended. If you ask any hotel concierge in the area, this would be their top recommendation for breakfast.
DRINK
Coffee Shops
Tatte. A popular chain, but oh so cute! Be sure to get to the shop early to beat the crowds. You can coffee, coffee + pastry or brunch here.
Flour. We loved this place. Great coffee and an even better selection of baked goods. Less crowded than Tatte!
Waterfront
The Landing. A pop-up summer bar with great Corona-Ritas.
Tia’s. A great spot with harbor views and a ton of patio space.
The Black Rose. An Irish pub with great live music.
Bell in Hand. The oldest continuously operating brew pub in America.
Trillium on the Greenway. Summertime pop-up bar located on Atlantic Ave right in front of the Boston Harbor Hotel.
Fort Point Channel Lookout District/Seaport
The Lookout Rooftop and Bar. Located on top of the Envoy hotel, I’d say they have some of the best views of Boston! We’d highly recommend making a reservation for the cocktail lounge area!
Cisco Brewers Seaport. A summer pop-up spot made entirely of shipping containers. They serve brews crafted in Nantucket!
Lawn on D. A great outdoor space for you to hang and get your Sunday Funday on.
Legal Seafood rooftop. Rivals the Lookout on views and has great sushi and oyster options to pair with your cocktails
George and I loved our summer trip so much, we decided to make it an annual occurance (check out my Portland, Maine travel guide HERE). We will be back. Happy travels!
