The Complete Boston Weekend Itinerary

Boston was one of those places I knew I’d eventually visit, but it was never at the top of my bucket list. Imagine my surprise when I spent a weekend there and fell in love with the city. There’s an extraordinary amount of history at every corner, the lobster rolls are delicious, and even with all the commotion that comes with a big city, it has a small-town charm. Follow this itinerary to get the most out of your weekend in Boston.

Beacon Hill

Start your day off in Beacon Hill, one of Boston’s oldest (and most photogenic) neighborhoods. It’s known for its historic architecture and Victorian-era homes. Grab breakfast at Tatte Bakery (70 Charles St), a very IG-worthy cafe with multiple locations all around the city.

Afterward, head to Acorn Street for a photo on one of the most photographed streets in the country. You might be able to avoid a long line if you get there early enough. Louisburg Square is another picturesque area in Beacon Hill.

From there, it’s a short walk to Boston Common, America’s oldest public park, and the beginning of the Freedom Trail. 

Freedom Trail

Freedom Trail marker

If you do only one thing in Boston this weekend, it should be the Freedom Trail. It’s the best way to get to know the city as it takes you through some of the most historically significant sites in U.S. history. The 2.5-mile red-brick trail goes from Boston Commons and ends at the Bunker Hill Monument.

The stops include:

  • Granary Burying Ground – the resting place of many notable Americans, such as John Hancock, Paul Revere, and Samuel Adams
  • Old Corner Bookstore – one of Boston’s oldest buildings
  • Old South Meeting House – the site the Boston Tea Party began
  • Boston Massacre site
  • Paul Revere House
  • Old North Church – the site that began the American Revolutionary War
  • USS Constitution – the oldest commissioned warship afloat

You can go at your own pace or book a tour complete with a guide in colonial gear.

Faneuil Hall & Quincy Market

One of the stops on the Freedom Trail is Faneuil Hall. Constructed in the 1700s as a center of commerce, Faneuil Hall served as a meeting hall and hosted America’s first town hall meeting.   

Just behind the building is Faneuil Hall Marketplace, which consists of Quincy Market, North Market, and South Market. Quincy Market is the perfect spot for a quick lunch since there are many food options, but since you’re in Boston, I’d recommend a lobster roll and some chowder!

Fenway Park

Fenway Park | boston weekend itinerary

Fenway Park is home to the Boston Red Sox baseball team, and while I am by no means a Red Sox fan (Go Rays!), it’s still pretty cool to see the ballpark in real life. The park is iconic and is home to numerous memorable moments in baseball history. The one-hour guided Fenway Park tour takes place year-round and even gives you a chance to sit atop the Green Monster.

Boston Public Library

I love a pretty library, so we had to stop by the Boston Public Library. The Boston Public Library (700 Boylston Street) is easily one of the most stunning libraries in the country. The library has multiple entrances, but I’d recommend going through the Dartmouth Street one or just following the signs for the McKim Building.

From the lion statues on the grand staircase to the mosaic-tile ceilings, there’s so much to admire before you even get to Bates Hall, the library’s most photographed room. You can take photos inside the hall, but try to be mindful of those using the space to read and study.

North End

Cannoli from Modern Pastry | boston weekend itinerary

The North End is known as Boston’s Little Italy. You’ll find plenty of pizza, pasta, and cannolis. As far as cannolis go, a few places claim to have the best ones in Boston, but you can be the judge. Mike’s Pastry, Modern Pastry, and Bova are within walking distance of each other in the North End.

Newbury Street

If you’re looking to do some shopping, Newbury Street is the place to do it. There’s a mix of boutiques and well-known brands, like Allbirds, Lululemon, and Muji. If you need a midday pick-me-up, Cafe Susu is a super cute coffee shop inside Suitsupply.

See the Mapparium

The Mapparium is one of the coolest things to see in Boston. Inside the Mary Baker Eddy Library is a giant, three-story-tall, stained-glass globe with a walkway through the middle. Once you’re inside, make sure to whisper. Because of its shape and glass walls, sound bounces back to the center so you can hear EVERYTHING.

Since the Mapparium was painted in 1935, it reflects the world as it was at that time. You’ll notice many country names and borders have changed in the last 85 years.

Note: Photography is not allowed inside the Mapparium 

Visit the Isabella Stewart Gardner Museum

Courtyard in Isabella Stewart Gardner Museum

Isabella Stewart Gardner was a leading art collector who spent the late 1800s traveling around the Middle East and Europe, searching for art to bring back to Boston. Once her art collection outgrew her home, she purchased the land where the Isabella Stewart Gardner Museum sits today. One of the most distinctive features of the museum is the garden courtyard. Three floors of galleries surround the Courtyard, which is always blooming.  

The Gardner Museum is also where the world’s biggest art theft occurred. In March 1990, two men impersonating police officers stole thirteen art pieces. Museum officials are still searching for the pieces, and anyone with information leading to the recovery of one of the works can collect a $10 million reward. If you want to learn more, there’s a four-part Netflix documentary about the heist, This Is a Robbery: The World’s Biggest Art Heist.

More To Do

Boston skyline at night | boston weekend itinerary

Samuel Adams Brewery Tour

If you’re a beer fan, the Samuel Adams Boston Brewery should be on your list of things to do. They offer multiple tours where you can tour the brewhouse, learn about the brewing process, and perfect your pour technique. 

Seaport District 

While Downtown Boston is known for many centuries-old buildings, Seaport is experiencing a rebirth. Today, the neighborhood is full of luxury apartments, restaurants, bars, and shopping. Its waterfront location is a great place to enjoy drinks with a view. 

One unique spot is The Lawn on D. It’s an outdoor event space with food, drinks, and lawn games. You might recognize the circular swings that light up at night. Although it’s open daily, they close for private events, so check their calendar before you go.

Salem

If you’re into spooky things, visiting Salem is a must-do. It’s less than an hour’s drive from Boston, and there are public transportation alternatives if you don’t have a car. The Salem witch trials in the late 1600s have become a part of the city’s identity. All around Salem, you’ll find witch museums, historic sites related to the witch trials, and plenty of “haunted” places. 

While October would be the most obvious time to visit Salem, it’s undoubtedly the busiest. If you still want Fall vibes, consider going in September or November.     

Overall

Boston is an amazing city full of history and culture. From the Freedom Trail to the Seaport district, it’s a destination worth exploring. This itinerary should give you more than enough to do over a weekend in Boston. Enjoy your next trip, and make sure to have a lobster roll!

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