As one of the oldest cities in the United States, Boston, Massachusetts is a beautiful city completely ingrained in the history of the country. Boston is a perfect North American destination to spend a few days or a weekend!
My parents and I visited Boston on Easter long weekend and it was the perfect amount of time to explore the city. We had such a great time wandering through all of the different neighborhoods and following the Freedom Trail. I hope that this itinerary will help you on your future trips to Boston!
DAY 1
Back Bay and Newbury Street
Start your weekend in Boston by exploring the Back Bay area. Make your way to Boston Public Library by strolling through the streets lined with a mixture of beautiful churches, historical brownstone buildings, and skyscrapers.
Head inside the gorgeous library and make sure to check out the courtyard as well.
Head west on Boylston Street where you’ll pass by the Boston Marathon Finish Line. Keep walking towards the Skywalk Observatory, where you can choose whether or not you want to head to the top for views of Boston.
Walk down Newbury Street, one of Boston’s most famous shopping streets. An abundance of stores and restaurants are weaved throughout Victorian brownstone townhouses. Very unique and picturesque!
Boston Public Garden
The east end of Newbury Street will bring you to Boston Public Garden, a beautiful park in the middle of the city.
Pass by the Swan Boats on the way to “Make Way for Ducklings,” an adorable statue based on the book about a family of ducks who live in the Boston Garden. We were in Boston for Easter weekend so the ducks were dressed up, too cute!
Cheers
Directly across from the park on Beacon Street, you will see the famous Cheers Restaurant. This is the pub that inspired the television show “Cheers”. Take a look inside at both the upstairs and downstairs areas.
Beacon Hill
You are now in my favorite area of Boston, Beacon Hill. Take your time to wander the narrow gas-lit streets and appreciate the beautiful historical homes.
DAY 2
Freedom Trail Walk
Time to learn all about the American history that took place in Boston! The Freedom Trail is 4 km long and has 16 locations. There are tours available, but only of 11 sites. We opted for a self-guided walk of all 16 sites and it was awesome!
To read my blog post, “A Self-Guided Tour of the Boston Freedom Trail,” click here.
Quincy Market
You cannot visit Boston without stopping at Quincy Market. It is located right next to Faneuil Hall (a Freedom Trail site), so make sure to check it out in-between all that history!
North End
A section of the Freedom Trail walk will bring you to Boston’s North End neighborhood. The North End is the city’s oldest residential area and has a large Italian-American community. Because of this, it’s filled with many cute Italian restaurants.
Charlestown
The Freedom Trail ends in Charlestown, a great little part of the city to walk around in. The streets are lined with adorable pastel-colored clapboard houses, typical of New England.
DAY 3
Boston Harbor
Spend your morning at the Boston Harbor by starting at Christopher Columbus Waterfront Park and following the Harborwalk trail to the Boston Tea Party Ships and Museum.
Inside the Museum, we visited Abigail’s Tea Room, where you can purchase a bottomless tea cup and sample the five different teas that were thrown overboard at the Boston Tea Party! You can also choose to tour the museum and its two replica ships.
Chinatown
A short walk will bring you to Boston’s impressive Chinatown. Take in the bustling energy and the mouth-watering Chinese and Vietnamese restaurants.
Fenway
From Chinatown you can take the T, Boston’s great subway system, to Fenway. Of course you have to see Fenway Park, home to the Boston Red Sox since 1912, with your own eyes. You can also take a tour of the baseball park or better yet, see a game!
Isabella Stewart Gardner Museum
A 15 minute walk will bring you to the Isabella Stewart Gardner Museum, my favorite attraction in Boston. Isabella Stewart Gardner was a well-to-do woman who lived in Boston and often travelled around the world with her husband. In 1903 she opened this museum and had it filled with her collection of paintings, sculptures, tapestries, furniture, and books that she acquired during her travels. Stunning and so fascinating!
Tip: buy your ticket in advance online.
Harvard
From the Museum of Fine Arts station, you can take the T to Harvard. Student-led tours of Harvard University run until about 3 or 4 pm, so you could always visit Harvard in the morning instead. We chose to walk around on our own.
Some additional Boston sites to visit are:
- Charles River Esplanade
- Museum of Fine Arts
- The New England Aquarium
- Museum of Science
- Boston Children’s Museum
- Harvard Museum of Natural History
- Arnold Arboretum of Harvard University
- The Institute of Contemporary Art
If you will be visiting the sites mentioned in this article and those on The Freedom Trail, many of them are included in the Go Boston Card: https://gocity.com/boston/en-us.
I hope you enjoyed this itinerary for a perfect long weekend in Boston!
To read my blog post, “Where to See Cherry Blossoms in Boston,” click here.
To read my blog post, “What and Where to Eat in Boston,“ click here.
