A Complete Weekend to Boston Trip Itinerary

Boston is the country’s oldest and most historic city. It’s the perfect balance of small-town charm and big-city hustle. Enjoy a stroll along cobblestone streets. Visit Harvard, the most profound university in the world. Catch a Red Sox game at Fenway. Eat at some of the best Italian restaurants. Boston has a little something for everyone to enjoy! If you’re looking to plan a weekend trip to Boston. This guide outlines a perfect itinerary to take in the best sights in Boston in only 2/3 days.

Things to Know Before Visiting Boston

When exploring Boston be prepared to walk A LOT! It’s a fairly small city that most can be covered on foot. So bust out those comfortable walking shoes!
Unless you’re staying outside the city center you won’t want to rent a car when visiting (parking in the city will cost you $40 a day) – it’s easy to get around by public transport or walking
The “T” is Boston’s subway system and you can purchase a reloadable Charlie Card (Bostons equivalent to the metro card)

Best Things to Do in Boston

Walk the Freedom Trail

The Freedom Trail is a 2.5-mile walk through Boston that covers 16 significant places of history that impacted the American Revolution. This trail was preserved and dedicated to the city of Boston in 1951 and today over 4 million visitors take this walk annually. This trail covers Boston Common, King’s chapel & kings burying ground, granary burying ground, the old south meeting house, the old state house, the old north church, and many more. You can cover a lot of ground when walking the freedom trail and should be experienced by all who visit.

Visit Beacon Hill

Notably, the most charming neighborhood in Boston and maybe even the US is Beacon Hill. Beacon Hill is home to The Historic Massachusetts State House, gaslight narrow streets, and picturesque homes lining a cobblestone street. For the most popular part of Beacon Hill, visit Acorn Street. Finally, the original Cheers Bar is located at 84 Beacon St.

Visit Boston Common

The famous public park where the infamous movie “Good Will Hunting” was filmed is called Boston Common. It’s also the oldest public park in the entire United States dating back to 1634. Some refer to this part of the city as the heart of Boston, and I can completely see why. Aside from the fact that back in the day this was a place of public punishments, it’s one of the prettiest parks I’ve been to. Adjacent to the common is the Boston Public Gaden. Both of these parks span across 44 acres in downtown Boston and is the perfect place to spend an afternoon.

Explore the Back Bay Neighborhood

The Back Bay neighborhood spans around Copley Square and is a hip stylish neighborhood filled with the best shopping, art galleries, and patio cafes. A long walk on Newbury Street can take you to lots of trendy places. Back Bay also is home to the Boston Public Library and Trinity Church. Out of our entire Boston weekend trip, the library was my favorite part because it totally reminded me of Hogwarts. Also, the courtyard was an architectural dream. Don’t miss out on those 19th-century pieces of history!

Enjoy an Italian Meal in North End

The North End district is a lively neighborhood that is similar to that of Little Italy in NYC. It’s home to Boston’s oldest residential neighborhoods and spans one square mile on Bostons waterfront. Some of the best Italian food on the east coast can be found here. Finally, if you visit this neighborhood Mike’s Pastry is a right of passage. Their cannolis are delicious and the size of your head. It’s well worth the hour+ wait in line.

Visit Cambridge and Walk Around Harvard

Cambridge is a college town known for being home to the most prestigious Ivy League school in the United States, Harvard. But Cambridge is so much more than a college town. It’s located along the Charles River which showcases beautiful views of Boston, has a great foodie scene, and a thriving music and art scene. You can easily spend an entire afternoon exploring all that Cambridge has to offer. Finally, a walk through the hallowed halls of Harvard and Harvard Square is a must!

Explore the Market District

Bostons Market District dates back to the 1700s and is home to the Boston Public Market also known as Fanueil Hall. It’s located in downtown Boston steps away from the waterfront and is home to 70 retailers. It’s best to come here hungry and experience worldwide cuisine, pubs, restaurants, and the world-famous Quincy Market Colonnade. Finally, you can easily post up and watch the street performers and musicians who fill the cobblestone streets.

Eat the Original Boston Creme Pie

The Boston Creme Pie is an iconic culinary creation that dates back to 1856. The Omni Parker House hotel was the original creator and they still serve the timeless recipe today! They have since shared the recipe for you to make at home but if you want a taste of history visit one of the hotel eateries.

Visit the Isabella Stewart Gardner Museum

This famous art museum houses significant examples of European, Asian, and American Art. It is notably known for its stunning courtyard gardens and unfortunately the art heist that took place here in 1990. Sadly, 13 pieces of art were taken during that theft and still to this day remain an unsolved mystery. Nevertheless, a visit to this museum

Boston Weekend Itinerary

Friday

Either drive into Boston or fly into Logan International airport
2 pm check into your hotel
Walk the Freedom Trail
Walk around Boston Common and enjoy the scenery
Have an early dinner and catch a baseball game at Fenway Park

Saturday

Start your day in Cambridge to visit Harvard Square and have brunch
Visit the Back Bay neighborhood to do some shopping and have lunch
Explore the Boston Public Library + Trinity Church
For dinner, have a nice Italian meal in North End
Visit Mike’s Pastry Shop for a late-night snack

Sunday

Grab brunch in Beacon Hill and explore one of the cutest neighborhoods in Boston
Visit the Isabelle Stewart Gardner Museum or the New England Aquarium
Have lunch at Faneuil Hall Marketplace and watch the street performers perform
Walk over to the waterfront and check out the Boston Tea Party ships

Thank you for reading my “Complete Weekend Trip to Boston Itinerary”. What are some of your favorite Boston spots to visit? Finally, don’t forget to check out more of my USA Travel Guides.

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XO,

Courtney