Boston is a historic city filled with modern residents. This fast-paced metropolis is becoming a trendier vacation destination for people who want to see historic sites, ocean views, and a flavor of Europe in an American city!
Boston is great for a long weekend or as a starting point for your trip around New England. You can see flowers blooming in the spring, visit the local beaches in the summer, or check out the foliage in the fall.
Driving around the city can be daunting, but the downtown is very walkable and the city recently installed miles of bikes lanes to help push people to travel greener. When planning out your day, be sure to check the weather as it changes quickly, and you might need to rearrange your schedule to take advantage of the sunniest days!
What To See
The North End
Boston’s Little Italy is one of the most photogenic neighborhoods in the city. The buildings are all brick and copper, with little shops and restaurants tucked down staircases and hidden along side-streets. The best time to visit is during the weekends in August to see the Fisherman Festival and Festival of Saint Anthony when the neighborhood is full of parades and vendors selling authentic Italian street food.
Christopher Columbus Park
Located right next to the North End, Christopher Columbus Park is an Instagramer’s dream! It has views of the harbor and vine-covered archways. During peak times, it will be hard to get a photo without people in the background, but it is an amazing spot to shoot early in the morning when the sun is coming up over the water.
Imagine historic brick townhouses covered in ivy, cobble stone sidewalks, and old-fashioned lampposts and you’re picturing Beason Hill, one of Boston’s wealthiest neighborhoods! Home to revolutionaries and famous authors, like Silvia Plath, Robert Frost, and Louisa May Alcott, this neighborhood is worth exploring (and its own photoshoot). If you’re up early enough, you might be able to take photos on the infamous Acorn Street before the crowds get there, but if you want to avoid cropping people out of your pictures, walk a little farther and visit Cedar Way for a quiet row of brick stone buildings or Spruce Place for a cobblestone road.
In the heart of the city, the Boston Commons and Garden are little green gems! In the spring and summer, the Gardens will be full of flowers. In the fall, crisp leaves will cover the ground, and in the winter, Frog Pond turns into an outdoor ice rink for everyone to skate on. This is a great spot to take pictures of the swan boats, city skyline, and the iconic statue that greats you at the entrance to the Gardens.
Boston Public Library
While you’re in the area, why not check out Newbury Street and the Boston Public Library. Newbury Street is the place to shop in Boston and has a mix of high-end stores and local favorites.
The Boston Public library is divided into two halves: one is a modern library, and the other is a grand stone building that includes a museum and a hidden courtyard that’s great for both reading and photography!
Whether you’re into academics or movies, you’ve heard of Harvard, but you might not be familiar with the cute area around the campus. You’ll find lots of historic brick buildings, trendy restaurants, and tons of Harvard apparel nearby to pose with. Plus, you’ll have more than one opportunity to try out your best Boston accent saying “pahk the cah on hahvahd yahd.”
Another can’t miss Boston icon is Fenway Park! One of the oldest baseball stadiums in America, Fenway is for more than just baseball fans. Going to a game (and getting Fenway Franks and beers) is super fun even if you don’t follow the sport. If you do love baseball but couldn’t get tickets to a game, don’t worry! You can watch from the Bleacher Bar, which looks out over the field, and feel the stadium’s excitement.
Where To Eat
In the North End, check out Ernesto’s! This hole-in-the-wall pizza shop is known for selling huge slices for cheap (by Boston’s standards). Each piece is really a quarter of a pie and there are a lot of toppings to choose from. If you can’t find a table in the shop, try walking a little bit and eating on the Greenway.
In Faneuil Hall, Quincy Market, a historic bazaar, has a ton of options when it comes to food. You can get New England classics like clam chowder and lobster rolls as well as food from around the world. It’s great if you’re traveling with a group or a picky eater, since everyone can visit a different booth and get what they want.
In Beacon Hill, check out Tatte Bakery! This local chain is a huge hit for breakfast with picturesque pastries and gram-able tiles in each location. I’d highly recommend trying the shakshuka while your there. This North African/Middle Eastern tomato and egg dish recently took the Boston brunch world by storm and is something you will definitely want to try again!
In Harvard Square, don’t miss Bartley’s Burger Cottage. This packed little burger joint is the go-to place for Harvard students (and tourist) for a reason. The burgers are delicious, named after Boston pop culture icons, and begging to be on your feed! Be prepared to make friends since this tiny spot has you share tables with other groups who are also pumped to try the food!
In the Seaport, you should visit the Barking Crab. It’s truly an experience to eat seafood right on the water! This spot has been a local favorite for years, and even appeared in a couple of Boston-based movies. Make sure to put your name in early since this place is known to have a long waiting list during the summer.
Where To Drink
If you’re looking for a view, you can’t beat the Lookout Bar in the Seaport. This rooftop bar looks out over the city and the harbor, and it is open year-round, which is huge for an outdoor space in Boston. Enter through the hotel below, and don’t expect to get into one of the heated igloos on a chilly winter night since only a couple are open to the public.
Moving over to the Fort Point neighborhood, there are a lot of great places to go out. Drink is a more hidden bar that doesn’t have a drink menu at all! You tell the bartender what kind of drinks you usually like and what you’re in the mood for, and they whip up a drink just for you. Nearly every drink is very gram-able, but you can always order based on looks if you want something that really stands out.
Right down the street from Drink (with another location in Back Bay) is Lolita’s Cocina & Tequila Bar, a great place to go for food and an even better place to grab a drink. They have a wide variety of margaritas that never fail to please and an atmosphere you will want to post everywhere. The Fort Point location has an outdoor patio that looks out over the city and the water. Plus, it makes you feel like you’re in a hidden cave in Mexico that just might be hiding the fountain of youth. Definitely someplace you’ll want to check out!
Looking for a more relaxed vibe? Boston’s brewery scene has exploded in recent years, creating lots of places to spend an afternoon with some friends, including a lot of pop-ups on the Greenway. These pop-ups change pretty regularly, but never disappoint. There is City Winery near South Station, Trilluim Brewery farther up by the Harborwalk, and Night shift Brewing along the Esplanade. All are outside, and each offers some great photo-ops.