Discover the Best Sights to Visit in Boston, MA

Boston, Massachusetts has always held a significant place in my heart. This great city cannot be skipped when planning a New England trip! Famous for its chowder, supposed accent, and champion sporting teams, Boston is a bustling city with a little something in it for everyone. (It’s also heavily known for its Irish influence, often reminding me of my time spent in Ireland)

 Growing up around 45 minutes out of the city, it was always a special event to go into town. Now that I live here, I have the opportunity to explore the ins and outs of the city every day! It wasn’t until I moved away from Boston that I could appreciate the energetic exclusiveness that comes with being from Massachusetts. Almost everywhere in the world, tourists can be found proudly wearing a Boston sports logo, or a university sweatshirt. Wearing a Patriots jersey in Texas, I was called a band-wagon fan! That’s the irony of a hometown I guess… the farther away you go the more you miss it. 

A few things to know before you plan a trip to Beantown: almost none of us say chowdah or Hah-vahd, we all exclusively run on Dunkin’ Donuts (and vehemently reject the brand shift to ‘Dunkin’), and we all stand forcefully, spiritedly, and proudly behind the Boston Strong slogan. 

There’s so much more to Boston than Faneuil Hall or Newbury Street, so grab your Dunkin’ Donuts iced Caramel Swirl coffee and read about my favorite local must-see destinations. 

Where to Stay:

The Copley Square Hotel, built in 1891, is the city’s second-oldest hotel. The ultra-luxurious accommodation features spacious rooms and unbeatable views of historic Boston. Baseball Hall of Fame legend Babe Ruth is among the many celebrities known to frequent the hotel! Located conveniently in Copley Square, you have quick walking-access to Newbury Street, the gardens, and hundreds of delicious restaurants and bars. Fun fact; my prom was held here!

Another incredible place to stay is the Liberty Hotel. This grandeur building actually has a rich history behind it, as it used to be the Charles Street Jail. This prison was established in 1851 and housed Boston’s most notorious criminals for 120 years! In 1973 the court ruled the jails’ living conditions inhumane, but continued to let it operate until 1990. The 298 jail cells have been renovated into comfortable suites but decorated with authentic jail-bars on the windows. A blend of history and high-style elegance, and a name dripping with irony,  this hotel is the quintessential Boston experience. 

In addition to Copley Square and Liberty Hotel, there are hundreds of hotels within the city that fit all budgets, as well as countless Airbnb’s! 

Where to Eat:

If you’re looking for award winning entrees, head over to Fox & The Knife for dinner. The refined, award-winning Italian restaurant, located in South Boston, is inspired by Modena, Italy, where Chef Karen Akunowicz spent more than a year studying culinary arts. It’s casual contemporary setting allows guests to focus on “celebrating the everyday joys of great company and good food”. Reservations are tough to get though, so plan in advance if you want a table.

Another delicious but more affordable restaurant in the area is Daedalus, a modern American-styled rooftop bar. The outdoor seating offers a relaxed atmosphere for any casual night out on the town. Reservations are required for rooftop seating, as it is limited and highly desirable, but Daedalus offers street-level outdoor seating as well as indoor options on rainy or chilly nights. Be careful when looking at their online menu though, as it changes almost weekly!

Where to Drink:

The Alibi is a high-end styled bar set within the Liberty Hotel. Themed appropriately with the building’s history, The Alibi offers a true-crime themed menu with cocktails such as “Whitey Bulger” (my drink of choice), “Solitary Confinement” and “Sawney Bean”. With both indoor and outdoor arrangements, the environment is decorated with infamous mugshots of criminals and celebrities, along with individual iconic quotes regarding their arrest. 

You cannot visit Boston without having a beer or a cocktail at the infamous bar, Cheers. Known for its’ 1980’s sitcom, the bar is always full of friendly customers and live music. The menu is themed with meals based on the show’s characters, crafted similarly to the sitcom’s menu. As a bonus, you’ll get to take home your own souvenir glass. 

In addition to visiting bars, enjoy an afternoon at one of the many Boston breweries, my personal favorite being Downeast Cider House. The Boston-based company ferments a variety of flavorful year-round and seasonal ciders. My personal favorite is their pumpkin flavor! Tours of the cider house are hard to come by, as spots fill up weeks in advance. Plan accordingly and get ready to taste all sorts of delicious blends!

If you’re in need of a quick coffee break, head over to Tatte Bakery. This aesthetically pleasing Boston-based bakery is committed to quality lattes within a homey, pleasant atmosphere. Renowned for its pastries, Tatte has become a beloved location for Bostonians and tourists alike. 

Things to Do:

The most beautiful parks in Boston are the Boston Public Garden and Boston Common. The Common, known for its historical significance, is a 50-acre urban park created in 1634 filled with monuments – making it the oldest American public park. It connects to the Gardens, a more scenic public area with canopying trees and a beautiful pond. Both locations are great for a casual stroll with your dog or a picnic. These centrally located public greens can be found whilst walking the Freedom Trail, a 2.5-mile tour stopping at 16 of Boston’s nationally significant historical sites. 

Another staple place to visit is the Harbor (not the Hah-bah), infamous for the Boston Tea Party. If nothing else, you’ll remember learning about the tea party in High School. On December 16^th, 1773, a bunch of men who called themselves Sons of Liberty said “no thanks” to Great Britain’s taxations on tea. In protest against fees on their midafternoon drink, the men threw crates of tea bags into the ocean. The rumor is that the ocean became brown with tea, but honestly have you ever tried to steep a tea bag in cold water? It’s not happening.   

After all, I did mention Newbury Street, so might as well talk about it. Located in the Back-Bay area of Boston, it’s the street where you’ll shop till you drop (or at least until your bank account does). High-end fashion to consignment shops, incredible restaurants to one-stop coffee shops, you can find it all on Newbury!

Another must-see is Faneuil Hall, the location of America’s first town meeting. Nicknamed the “Cradle of Liberty” for its significance towards the building of America, the hall has hosted speakers such as George Washington, Samuel Adams, Susan B. Anthony, and many more. It’s most known for the Quincy Marketplace adjacent to the building, where 36 international food vendors provide every type of cuisine you could think of. Whatever you’re in the mood for, the marketplace has it all. Quincy Marketplace is also the hub of many street artists, you will always hear someone performing a variety of unique talents. 

Of course, our sports industry cannot be compared to the other states. The New England Patriots, the Red Sox, the Celtics, and the Bruins are decorated in hundreds of championships and awards. Growing up, I thought every state had their own “champion” sports teams, I didn’t connect the pieces that the states competed against each other. Clearly, I don’t watch sports. Make sure to visit Gillette Stadium or Fenway Park and grab a Fenway Frank! It’s the best way to wrap up your Boston experience. 

Overall, there are hundreds of unmentioned hidden gems around the city, I could never name them all. Boston is, from a completely unbiased opinion, one of the most beautiful cities in the nation. I’ve never met someone who didn’t enjoy their time visiting. You’ll never be bored! Thank you for reading about my favorite destinations to visit around Boston, I hope you enjoyed this article!

For more activities to do, check out my list of Free things to do in Boston or Best Winter Activities to do in Boston! If you have any follow up questions about something I didn’t cover in Boston, please email me at hello@alostblonde.com

♡ Abigail Reagan