Boston is the perfect size for a weekend getaway. There are enough things to do that you’ll leave wishing you’d had more time to see them all, but you’ll also feel like you’ve experienced much of the city. Boston is also one of the few places where the typical tourist attractions actually live up to the hype (which is a miracle, if you ask me). After hoofing it across the city for two days straight, I got a good feel for the types of things to do in Boston.
Here are the things you need to do when you visit, in no particular order.
If you’ve never been to Boston, the Freedom Trail is a must. It’s 2.5 miles long and takes you through Boston’s iconic Revolutionary War sites. Though the trail is packed with tourists, the rich history of the city more than makes up for the crowds. To see which sites you should and shouldn’t skip, make sure to read my handy guide.
Beacon Hill is the ritzy area of Boston and is too beautiful to miss. While there’s nothing to do in Beacon Hill in terms of attractions, you’ll have no problem passing the time staring at gorgeous brownstones—seriously, the window boxes here are next level.
While in Beacon Hill, you need to hunt down Acorn Street. Acorn Street is the most photographed street in Boston and looks like it was taken from a Better Homes & Gardens magazine. If you’re itching to get lots of photos here, I’d recommend visiting in the morning before others get the same idea. The tiny alley gets clogged with visitors quickly (can’t imagine living here myself, too many people!).
The North End
Ask any Bostonian what you need to see in the city, and their first answer will likely be the North End. This area is home to most of Boston’s Italian restaurants and bakeries, as well as many of the more exciting Freedom Trail sites. Odds are, you’ll find yourself in the North End for a mid-afternoon cannoli every day of your visit. You’ll hear no judgment from me, I did the exact same thing!
The brownstones along Commonwealth Avenue give Beacon Hill a run for its money. The avenue is split by a grassy area for people to walk down and oogle the homes. It’ll take you a little over 30 minutes to walk down, and you’ll definitely want to bring your camera along!
Once you’ve walked down Commonwealth Avenue, take a left and walk down Newbury Street. Parallel to Commonwealth Avenue, Newbury Street is full of shops and restaurants. The shops are a decent mix of local boutiques and chain stores, but all look absolutely adorable in the brownstones.
Boston Common & Public Garden
The Boston Common and the public garden are right next to each other and are smack in the middle of the city. After a few hours of walking around the city, circle back to the garden and relax on a park bench. You can watch Boston’s iconic swan boats drift by in the public garden (best of luck not dozing off for a few minutes).
The Charles River is another great place for a stroll after you’ve had your fill of downtown. If you’re lucky, the Harvard rowing team will be on the water. It makes for one heck of a photo!
Boston Public Library
Just a short walk from Newbury Street, the Boston Public library is stunning. It has a main reading room that rivals New York City’s library, and a main courtyard that will have you googling how expensive it’d be to host your wedding here. You can explore the library solo or join an hour-long tour.
Harvard is almost synonymous to Boston. You can’t think of one without thinking of the other. Harvard Yard is smack in the middle of Cambridge and is the oldest section of the university. This grassy area is also beautiful, and you’ll feel smarter just by touring the campus.
Museums to Check Out
Even if you’re only in the city for a weekend, you should still check out one of its museums. While there are lots of museums to choose from, the following are some of my favorites.
Isabella Stewart Gardner Museum
I’m pretty sure I’m going to write an entire post about this museum, because it’s just that amazing. This “museum” was once the home of a woman who was filthy stinking rich and dedicated the latter half of her life to collecting art. She transformed her home into a museum and left it to the city after she died. The art was thrown together in the most hodgepodge way, but is incredible to look at. Oh, and did I mention the giant indoor courtyard? (see above)
Museum of Fine Arts
If you’re looking for a more traditional art experience, the Museum of Fine Arts is for you. With the usual mix of paintings and statues, this is a solid place to spend a rainy afternoon.
Harvard Museum of Natural History
This is a good museum for people who hate museums. It’s on the smaller side since it’s a university museum, but there’s a decent variety of exhibits. The museum is centered around nature (go figure) and has a lot of flower and animal exhibits.
Restaurants to Try
Boston has lots of great restaurants that are worth checking out, but here are a few that my stomach particularly enjoyed.
If the line at Mike’s Pastry is too long for you (which is always), try a few treats from Bova’s. A family-run bakery, Bova’s cannoli are amazing, as are their butter cookies and cheesecake.
Mike & Patty’s
With only five chairs to sit in, Mike & Patty’s isn’t the ideal sit-down breakfast location. But what they lack in seating, they more than make up for in their bomb breakfast sandwiches. They have a no-frills bacon, egg, and cheese sandwich, but their “fancy” option is also good (avocado, onion, and a few other tasty bits).
Though Saus has some sandwiches on the menu, the main event is their Belgian-style fries. With 15 specialty dipping sauces to choose from, the hardest part about ordering is figuring out which one you want to go with your twice-fried fries. Don’t worry, you can order extra sauce for a small fee.
South End Buttery
This place dishes up solid, no-frills breakfast. The pancakes here are massive and super fluffy, and the breakfast sandwich is on point. It can get quite loud inside when the dining room is full, so be ready to shout to be heard.
Boston Public Market
Although this isn’t a standalone restaurant, the Boston Public Market is certainly worth visiting for a quick bite. Here you’ll find lots of different food vendors, all of which use locally-sourced and locally-prepared food. Whether you’re craving falafel, seafood, or a hearty corn beef sandwich, you’ll find what you want here.
This list is fairly long, but you really can do all these things in one weekend. With the exception of the museums and Harvard Yard, you can also walk to everything on this list, meaning you’ll be able to spend a little extra at Boston’s fab restaurants (score!).
Is Boston on your bucket list? Tell me what you’re most excited to see!