Shortcut Travel Guide to Boston
Shortcut Travel Guide to Boston (click to enlarge)

For first-time visitors of Massachusetts’ capital, exploring Boston can be filled with history lessons, sightseeing tours, and food tastings. There’s so much to do and appreciate in this eclectic city that it’s easy to get overwhelmed and not even know where to start.

Before diving into the list, let’s appreciate some of Boston’s amazing qualities. This city carries so much of our nation’s history everywhere you go. It’s hard to vacation in Boston without noticing the character of the architecture and beauty of every park or harborside view.

Beantown can also be packed with a wide range of things to do, see, and eat without being completely overwhelming. It’s the perfect middle-ground for when you need to branch out from the small-town life or need to make the escape from New York to Boston to downsize from the crowds.

Unlike NYC, Boston is small enough to be a pretty walkable city with a few T stops in between, which means that you don’t have to spend all your money on multiple Ubers just to get around. Plus, you really get to see everything Boston has to offer when you get to walk around and explore different neighborhoods. Once you spend some time getting to know the city, you’ll find that every cobblestone road and hole-in-the-wall shop adds to the quaint charm of this enchanting destination.

For all tourists, travelers, and even those who call this city home, here is a list of the best things to do and eat in Boston.

Read more: Which historic U.S. city do you like the most? Boston vs Philadelphia

Where to Eat in Boston

Boston has some delicious and diverse food options, you just gotta know where to find them! Whether you’re looking for a sit-down dinner experience or just want to grab some quick bites throughout the day, Boston offers plenty of choices from food walking tours, to dim sum in Chinatown to a fancy night out at the Top of the Hub.

When you want a little of everything…

One of Boston's historic neighborhoods
One of Boston’s historic neighborhoods

The North End

You really can’t go wrong with taking a stroll through the North End for authentic Italian eats or just small bites along the way. Be prepared to wait for the more popular spots like Giacomo’s if you want a sit-down meal (although the butternut squash ravioli will be well worth it). The North End also features some amazing shops and bakeries like Bricco Salumeria & Pasta Shop where you can buy imported meats and cheeses or try their own homemade breads.

If you’re craving something sweet, a trip to the North End wouldn’t be complete without a cannoli. Most Bostonians have already chosen their side between Modern and Mike’s for their top cannoli pick, but you should visit both to settle the debate yourself!

Quincy Market in Boston
Quincy Market in Boston

Quincy Market

While Quincy Market in Faneuil Hall is the typical go-to for first-time tourists, there really is something new to try even if you’re a long-time visitor. With over 50 food stands to choose from, Quincy Market has options for every appetite, from classic Boston fare like clam chowder and Boston Cream Pie to Japanese and Indian cuisine. The crowds can get a bit overwhelming, so it helps to explore all of the options first so you know exactly what to get when it’s time to order. What’s the best solution? Buy a little of everything for the ultimate smorgasbord!

When you want to try something different…

Roxy’s Grilled Cheese

Let’s be honest, who doesn’t love an ooey, gooey, melty grilled cheese? Hands down, Roxy’s Grilled Cheese is the spot to go when you need late-night comfort food, a tallboy, and a round at one of their arcade games.

With two locations in Allston and Central Square, Roxy’s serves up the classics as well as unique combinations like Hot Honey Bacon and The Allston, with goat cheese, fig jam, and caramelized onions.

If you avoid dairy, you’re still welcome at Roxy’s as they offer vegan grilled cheese selections as well. Be sure to keep an eye out for Roxy’s food trucks around the city. They change locations daily so you don’t have to go far to get your hands on their famous grilled cheese.

The Beehive

Nestled in Boston’s South End is The Beehive, where live music, mouthwatering meals, and tasty cocktails meet in this funky yet classy setting. Original art pieces line the walls of this quirky establishment and new bands are featured nightly, ranging from jazz to reggae and cabaret.

The Beehive is a top choice whether you crave a leisurely Sunday brunch of Belgian waffles and poutine, or just want to enjoy a lavender margarita at the bar. If you anticipate sitting down for a full meal, however, a reservation will be the safe bet to get you in the door and seated. Otherwise, the bar will always have room for you to sit back and enjoy an after-dinner drink, especially on Friday and Saturday nights when the space is open until 2am.

What to Do in Boston

Endless adventures await you in the city of Boston. You can stick to tourist attractions like Duck Boat tours and the Freedom Trail or relax in the public gardens and shop through Harvard Square and Newbury St. It’s easy to rely on public transportation to get you from place to place and fit in as much as you can.

The Boston Waterfront
The Boston Waterfront

When you want to see something new…

The MFA & Isabella Stewart Gardner Museum

Home to pivotal art pieces by Claude Monet, John Singer Sargent, and Vincent Van Gogh The Museum of Fine Arts is a must-see in Boston. You can easily spend a whole day admiring the unique collections ranging from contemporary art and photography to musical instruments from the past. You can visit for free on Wednesdays after 4pm, but if you decide to check out the museum on a different day, you can return for free within ten days.

After you finish exploring, the Isabella Stewart Gardner Museum is right down the street. This home-turned-gallery features the many pieces of artwork, furniture, and rare books that Isabella Gardner had collected in her life throughout the 19th and 20th centuries and later put on display for the public. This is one of the most gorgeous and unique museums you’ll ever visit and it won’t be difficult to get lost in the magic and mystery of the old architecture and breathtaking courtyard.

New England Aquarium

The New England Aquarium is a go-to spot when you need a rainy day activity or just want to explore and interact with creatures that live below the shore. Perfect for families with young children or groups of friends, this harborside aquarium features exhibits where you can see some oh-so-adorable rockhopper penguins, seals, and jellyfish.

You can walk along a winding ramp that wraps around a mesmerizing 20,000 gallon tank featuring various sea life, including turtles, eels, and fish of every color. When your legs get tired, the aquarium also has a gigantic IMAX theater attached where you can sit back and watch 3D films about what lies beyond the deep.

Not only is the aquarium a fun day-time activity, but it really is a great way to sneak in some education about our ecosystem and the respectful way to treat those who inhabit it.

⇒ Get your tickets for the Aquarium and IMAX film

When you want some entertainment…

Charles Playhouse

If you’re looking for some evening entertainment, Charles Playhouse is an unbeatable option for a drink and a show. For over 175 years, this theater has put on some of the best performances in Boston, including Shear Madness, a production that’s been running for almost 40 years in the Playhouse.

Shear Madness is a hair salon murder-mystery where the audience can put together clues from the show and question the characters to figure out who the culprit is. Not only is this performance one of the most hilarious things you’ll ever be a part of, but the majority of the show is mostly improvised based on the interactions between the audience and characters. That means that you’ll be surprised by a different ending no matter how many times you attend.

Fenway Park
Fenway Park

Fenway Park

Let’s face it, if you visit Boston (during game season, of course) and don’t see the Red Sox play, did you really go at all?

Fenway Park is one of the most iconic sports stadiums in the nation and is a must-see spot when you visit Beantown. Even if you’re not the biggest baseball enthusiast, you’ll still have a great time with a beer and a fenway frank by your side. If you don’t get a chance to score a ticket, you can still take an hour-long walking tour of the park to see everything up close and personal.

For some added advice, if you plan to bring your car, leave it where you are. Parking fees can triple on game days but luckily the park has two T stops nearby. Public transportation will not only save you a ton of cash, but it’ll give you a better chance of making the game on time!

It really takes more than just a day to experience and appreciate the city of Boston. Each neighborhood has its own unique personality, from culture-packed spots like the North End and Chinatown to college-centric areas like Cambridge and Allston.

While this list named just some of the best eats and places to visit in Beantown, you should definitely ask around for local favorites if you’re not a fan of the more touristy options. As you explore the many unique and exciting activities that this city offers, be sure to give Boston the love and appreciation it deserves!

Where to Stay in Boston

Depending on what you want to get out of your Boston visit, there are many different areas of the city that are great for visitors. We like the Back Bay and Downtown neighborhoods because they are incredibly convenient to the top Boston attractions. Back Bay has a walk score of 96. Downtown has a 97. Beacon Hill is another area to consider, with a walk score of 98.

Here are our top affordable luxury hotel recommendations in Boston.

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ABOUT THE AUTHOR

Polina is an avid explorer and endless learner. During the day, she helps people find and book trips in North America and Europe at Wanderu.com.

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