Boston, Massachusetts

We first visited Boston, Massachusetts when I was in high school. At the time, I didn’t know what to expect, but the city quickly grew on me. Six years and three more trips later, I can now confidently say Boston is by far my favorite U.S. city. Boston stands out thanks to its dramatic history and unique neighborhoods (from trendy Newbury Street to the Italian North End). Additionally, the city’s camaraderie of residents (“Boston Strong”) makes Boston feel more like a tight-knit town than a bustling city. Plus, Boston is a great starting place for New England road trips to places such as Martha’s Vineyard.

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Where to Stay in Boston, Massachusetts

We have stayed in five different hotels in Boston, and each have their own character and perks. Ultimately, we have two clear front runners: the InterContinental Boston and the Lenox Hotel.

Located in the heart of Boston’s Back Bay neighborhood, the Lenox Hotel  is a family-owned four star hotel. The hotel boasts friendly and helpful service. Additionally, the Lenox has a great location: Copley Square, Newbury Street, and the Prudential Center are all within two blocks. Each room is carefully decorated, and the hotel is clearly a high-end boutique hotel. Plus, the Lenox is close to a T stop (Boston’s subway system), making it easy to get around.

If you would rather be near sights such as the North End or Quincy Market, the InterContinental Boston is great. While not quaint like the family-run Lenox Hotel, it offers the perks of a corporate hotel (i.e. gym and restaurant). Plus, the InterContinental offers fantastic views of the city skyscrapers or Boston Tea Party Museum, and an impressive downtown location.

Places to Eat in Boston, Massachusetts

Boston has many different neighborhoods, and even after four visits, we haven’t tried restaurants in many of them (i.e. Chinatown, or Back Bay). However, we do have some favorites we would like to share:

Regina’s Pizzeria

Regina’s is by far the restaurant we have been to the most while in Boston. Located in the Italian neighborhood of the North End, Regina’s is a very popular New York style pizza restaurant. Be prepared to wait for a table (Regina’s is so popular, there are heaters in the front awning for winter lines). But the hype (and the wait) is worth it. Pizzas come out piping hot and the cooks never skimp on cheese or toppings. Plus, the character of the packed restaurant, a pitcher of beer, and a massive pizza will be sure to get you in the mood for a slice.

Mike’s Pastry

Mike’s Pastry is another North End favorite. This pastry shop is best known for its cannolis, but also serves up everything from ice cream to decadent chocolate cupcakes. The restaurant only has a couple of tables, as the vast majority is used to hold the many lines of people waiting for a treat. In fact, during the heavy tourist season of the summer, Mike’s often has a line down the block! Don’t be deterred by the lines however: we highly encourage you to wait it out for a great treat.

La Famiglia Giorgio’s

Also in the North End (the Italian food in Boston is amazing, and it is very hard to choose just three restaurants), La Famiglia Giorgio’s is a lively restaurant that offers traditional Italian recipes all served family style. The restaurant is located just out of the main restaurant area of the North End, and offers a very Italian atmosphere.

Quincy Market, Boston

Quincy Market

This massive 1800’s food market is now home to a huge food hall. But don’t expect a food court: Quincy Market offers a vast array of unique cuisines. Plus, each shop is run by individual owners. Because of this, Quincy Market draws a crowd of tourists and locals, making it a buzzing and lively atmosphere. You can get everything from pizza to international cuisines to barbecue to desserts here, so make sure to come hungry!

Union Oyster House

Located on the Freedom Trail, this restaurant is supposedly the oldest restaurant in Boston. The Union Oyster House offers plenty of New England inspired seafood options and steak or chicken for those who would prefer meat. No, the food isn’t stellar, but we enjoyed the historic ambience of the restaurant. While this place does cater primarily to tourists (which we tend to avoid), we would still suggest going there because of its charm, location, and history.

The Black Rose

Located around the corner from Quincy Market and Faneuil Hall, the Black Rose is a traditional Irish pub. In addition to its prime location, The Black Rose offers plenty of indoor seating and good food, so you can take a break from the busy Boston streets.

Things to Do in Boston, Massachusetts

On the Freedom Trail, Boston

Freedom Trail

The Freedom Trail is a painted brick strip that connects Boston’s major historical sights. These include everything from Paul Revere’s House to Faneuil Hall to the sight of the Boston Massacre. To best understand these sights, visitors can choose to book a tour, purchase a book that explains each sight, or use online resources. This brochure gives an overview of each stop on the Freedom Trail so you can follow along while you walk. If you would prefer to go on a tour, head to the starting point of the Freedom Trail in the Boston Commons, and find the tour building for more information.

Newbury Street and Back Bay

Back Bay is located on the southeast side of the Boston Commons along the Charles River. While the neighborhood is home to the Prudential Center (huge shopping mall and conference center) and Newbury Street, most of the streets in this neighborhood are filled with residential brownstones. Walking up and down these well-kept streets is fun because it allows you to see some of Boston’s residential areas. In addition to being a residential neighborhood, Back Bay is the home of Newbury Street. Newbury Street is a trendy shopping street that is filled with cafés, restaurants, small shops, and chain stores. Plus, the street is bustling with shoppers, making even tourists feel like they are a part of the local scene.

Boston Commons

Boston Commons

Originally reserved as shared farmland for residents of Boston in colonial times, the Boston Commons is now a huge park in the center of the city. The grassy park also offers plenty of walking paths, a recreational lake for paddle boats, and a larger lake for strolling around. The Boston Commons also breaks up the historic Freedom Trail part of the city from the residential and shopping streets of Back Bay. Thus, the Commons act as a lovely walk between the two.

North End

Boston’s Italian neighborhood is called the North End. This dense community is home to countless Italian restaurants, including a few of our favorites: Regina’s Pizza, Mike’s Pastry, and La Famiglia Giorgio’s. The North End is also included in the Freedom Trail, as Paul Revere’s House is located in the middle of the neighborhood. We loved to walk around the North End during the evening, when the restaurants were busy and the community was alive.

Area around Quincy Market

Quincy Market and Faneuil Hall

Faneuil Hall was originally a key meeting place for colonists when planning and rebelling against British taxes and regulations. Over time, it transitioned into a market, and now hosts small stalls for souvenirs and gifts. Nextdoor is Quincy Market, a bustling food hall built in the mid 1800’s. These two buildings are a centering place for Boston’s tourism, and around them are a ton of souvenir shops, gift shops, and retail stores. Plus, many locals consider this area a great spot for lunch during a busy day at the office or an evening stroll, so it is always filled with people.

The Coop (Harvard Bookstore) on Harvard Square, Boston

Cambridge and Harvard Square

Across the Charles River is Cambridge, MA. While it is technically a separate city, Cambridge and Boston flow together and share the same subway system. Cambridge is best known for its two Universities: Harvard and MIT. Of the different areas in Cambridge, Harvard Square (located on the Red line of the T) is the best to visit. From Harvard Square, you can visit the Harvard Yard (the most historic part of Harvard University, and home to many of its undergraduate classrooms and freshman dorms), the Coop (Harvard’s library and clothing store), and the shops and restaurants around Harvard.

Day Trips from Boston, Massachusetts

Old Sturbridge Village

For those interested in getting out of the city for a day, Old Sturbridge Village is only an hour away. Old Sturbridge Village is the largest living history farm in New England, and offers guests the opportunity to explore what life was like between 1770 and 1830 in New England. The living history farm offers everything from a meeting house to a small town to an active farm for visitors to enjoy. Plus, there are live demonstrations and childrens activities (such as games and crafts) to keep the whole family engaged throughout the day.

Newport, RI

Newport, Rhode Island

Another fun day trip from Boston is Newport, Rhode Island. Located only an hour and 20 minutes outside of Boston, Newport is a feasible day trip. However, we made our stay in Newport a part of our New England road trip to better experience the town. In Newport, visitors can walk through town, visit the beach, and tour massive mansions (including the famous “Breakers” mansion, built and owned by the Vanderbilt family).