Three Perfect Days Exploring the Lesser-Known Sides of Boston

Boston, aka The Hub, the City on a Hill, and maybe less flatteringly, Beantown (due to the popularity of baked beans among its early settlers), is an easy-to-navigate metropolis made up of singular districts and vibrant neighborhoods, each well worth planning a trip around—in other words, it’s the perfect city for your next trip. Downtown Crossing, the Financial District, Chinatown, Fenway, Beacon Hill, and more hold a preserved national history while demonstrating their very own look and feel. Boston may be the butt of many jokes, but that just means it’s one of the most underrated cities in the country.

“One of my favorite parts of Boston compared to other cities is just how manageable everything is—you can walk most places across downtown/central Boston and it never feels overwhelming or too big to grasp like some other cities,” says Sophie Rae, an artist and graphic designer based between NYC and Boston. “For being such a big city, Boston has a true ‘town’ feel to it that is so comforting wherever you are.”

While it’s impossible to pinpoint every destination worth visiting across the city, particularly those spots outside of the touristy norms (we’re looking at you, Swan Boats), we’ve put together an itinerary approved by local experts that know Boston inside and out and have an appreciation for all there is to do in and around the city, whether that’s tailored to the museum-goer or seafood aficionado. Regardless of what drives you to Boston, you’ll discover that the city is a mecca for experiencing the old and new simultaneously—century-old restaurants with modern-day menus, historic buildings turned acclaimed hotels, and museums featuring works of artists both renowned and emerging.

Boston is a goldmine for those that love to explore and uncover hidden gems, and we strongly suggest venturing off the beaten path at times to experience the city’s true character.

See: The world renowned museums, like the Isabella Stewart Gardner Museum. Boston is home to quite a few famous museums that will tickle both your historical and art-loving fancy. Outside of the Isabella Stewart Gardner Museum, which houses a remarkable collection of Venetian paintings and archival objects (it’s also known for experiencing the single largest property theft in the world), there’s the ICA Boston, MFA Boston, Boston Tea Party Ships & Museum, Museum of African American History, Boston Children’s Museum, and even the Museum of Bad Art. “Keep in mind that certain days of the month there can be reduced or offer free admission, like MFA’s ‘First Fridays’,” says Bret Clancy, a Boston-based photographer.

Touch:  The Green Monster at Fenway Park. This iconic left field wall was designed in the early 1900s to keep fans outside the park from seeing Red Sox games for free. Now, it’s nothing short of Fenway’s most popular attraction where fans can not only sit, but if you’re within touching distance, you can swipe your hand across for good luck.

Smell:  The Atlantic. Technically, what you’re smelling is Massachusetts Bay, which is part of the Gulf of Maine, and thereby a projection of the Atlantic Ocean. Regardless, Boston’s spectacular waterfront is a can’t-miss. While you’re perusing, you might also get a whiff of the New England Aquarium, which sits right along the water. (FYI, you don’t have to get a ticket to see the seals—their exhibit is right outside the aquarium for your viewing pleasure).

Hear: Keytar Bear. If you’re a resident, you’ve likely been serenaded by Keytar Bear on the T—or he’s popped up in places like Copley Square. Dressed in a less-than-pristine bear costume from the movie Ted, Keytar Bear plays a mean keytar (a keyboard and guitar all in one), and they’ve been doing this for more than a decade now.

Taste:  Your way around the North End. A neighborhood fit for the pizza and pasta lover, the North End has no shortage of delicious carbs. Key streets to hit up, include Hanover, where restaurants like Giacomo’s and Carmelina’s sit, and Salem, where you’ll find La Famiglia Giorgio’s and Antico Forno. You should also give yourself time to try out Mike’s Pastry and Modern Pastry on Hanover Street to determine who has the supreme cannoli.

Boasting historic and national landmarks on what feels like every corner, Boston is a dream for those who can’t get enough of colonial architecture and tangible pieces of the past. “When you’re walking around, you’ll quickly notice Boston is filled with all kinds of history,” says Clancy. “People first think about the Freedom Trail, for example, but take a stroll up Acorn Street or ride the T from Park Street Station (the oldest subway in the US) and you’re already submerged in history. The old buildings interspersed with new also make for a nice contrast,” adds Clancy.

10 am - Reenact history by hurling tea into the Boston Harbor. 
You’re reading that right. At Seaport’s Boston Tea Party Ships & Museums, you’ll have an opportunity to take part in reenacting some of the city’s most iconic moments in history. Open throughout the week, a ticket to the museum will score you a fully guided experience provided by an enthusiastic costumed interpreter along with access to an 18th century replica vessel. You can also grab a bite to eat or a cold Sam Adams at Abigail’s Tea Room & Terrace.

11:30 am - Visit the birthplace of the Boston Abolitionist Movement.
Right in Beacon Hill, you’ll find the largest African American history and culture museum in New England. The Museum of African American History, open Tuesday through Sunday, spans two restored buildings: The African Meeting House, a registered National Historic Landmark, and the Abiel Smith School, the oldest public school in America built for educating African American students in Boston. The museum shares the important stories and voices within Boston’s Black community from the colonial period through the 19th century and beyond. You can also embark on the Black Heritage Trail, a 1.4-mile path through Beacon Hill, which showcases former private residences and community buildings that made waves during and after the Civil War. 

1 pm - Treat yourself to dessert at Parker’s Restaurant, the birthplace of Boston Cream Pie
Located inside the iconic Omni Parker House, which has welcomed hotel guests from Charles Dickens to Judy Garland, is the award-winning Parker’s Restaurant. First established in the late 1800s, the restaurant is famous for its ornate decor and hand-carved woodwork, but more importantly, it’s famous for whipping up one of the country’s favorite desserts: Boston Cream Pie. The dessert is still on the menu after all these years along with their Parker House Rolls dubbed “America’s first soft dinner roll.”

6 pm - Stop by The Liberty Hotel, aka the former Charles Street Jail. 
Head back to Beacon Hill for a look inside The Liberty Hotel. The hotel famously served as a jail from 1851 until 1990, then in 2007, it was officially converted into a 298-room luxe hotel. To check out the hotel’s storied past, you don’t even need to be an overnight guest. You can make a reservation or swing by the hotel’s on-site restaurants and bars, including Scampo, Alibi, CLINK., or the lobby bar.

9 pm - Have a pint at 21st Amendment. 
After strolling the streets (make sure to pop by Acorn Street, one of the most photographed streets in the world) stop for a pint at 21st Amendment. Paying homage to the end of Prohibition, this lowkey tavern will take you back in time with its old-timey pub aesthetic and no-nonsense food and drink menu. We also recommend Teddy’s on the Hill, where The Red Hat formerly sat before it officially closed in 2021. Prior to closing, the famous bar, which served as a real speakeasy during Prohibition, had been in business for over a century.

While the city is revered for its historical touchpoints and landmarks, there’s a lot to be said for Boston’s art and culture scene. “It’s thriving if you know where to look,” says Rae. “With so many students flowing in and out of the dozens of schools in Boston, the city also does a good job of catering to the young and open-minded community,” adds Rae.

10:30 am - Tour the Boston Public Library’s main building, the McKim Building. 
The Boston Public Library was one of the first free, municipal libraries to be established in the United States, and still operates as such today. Its McKim Building doubles as a museum filled to the brim with history, rich architectural design, and Renaissance-inspired artwork. For example, the building’s lobby, where you’ll find its grand staircase, is surrounded by murals said to be the only works commissioned outside of France by painter Pierre Puvis de Chavannes, one of the greats of the 19th century. You’re free to roam the library and uncover all its gems on your own, including Bates Hall Reading Room and the outdoor courtyard (just make sure you’re respectful to those utilizing the space) or you can schedule a free tour any day of the week except Wednesday. 

12 pm - Check out Graffiti Alley in Central Square.
Central Square in Cambridge is hip in comparison to its affluent counterpart, Harvard Square. Here you’ll find restaurants by day and basement clubs by night, like The Middle East, or The Garment District, a massive clothing warehouse filled with vintage, contemporary, and costumey options. But more importantly, Central Square’s public art scene has some of the best works in Boston, particularly in Graffiti Alley. The 80-foot alleyway located at 565-567 Massachusetts Ave is one of two legal spray painting walls in Massachusetts, where it serves as a colorful canvas for local and traveling artists alike.

2 pm - Visit the ICA along the waterfront.
Founded in 1936 as a sister institution to New York’s MoMa, the Institute of Contemporary Art (ICA) in Boston has showcased contemporary art by emerging and established artists for nearly 90 years. You can easily spend all afternoon exploring the works of visual art, performance, film, video, and literature—not to mention the building is art in itself. The 65,000 square-foot space, designed by award-winning architects Diller Scofidio + Renfro, sits along the water’s edge, “producing shifting perspectives of the waterfront throughout the museum’s galleries and public spaces,” according to ICA’s website. In other words, this is a view you don’t want to miss during your Boston travels. “The gift shop is amazing too!” Rae adds.

5:30 pm - Grab dinner and drinks at Yvonne’s in the Theater District.
A long day absorbing Boston’s art scene calls for a top-notch dinner. After sprucing up, head over to Yvonne’s for a cosmopolitan dining experience set in Downtown Crossing. Taking cues from the early beginnings of supper clubs, Yvonne’s luxurious, dimly lit 160-year-old interior is decorated with stunning accents of marble and mahogany, with comfortable seating surrounded by bookshelves and brick walls. The menu has plenty to choose from with small plates and snacks to Feast options as well as a cocktail list that takes inspiration from the classics. (Let it be known, you can get a pretty mean Espresso Martini here.)

8 pm - See a show at The Wilbur in the Theater District.
Close out the night with a live show at The Wilbur, the century-old arts theater that hosts nightly events from your favorite comedians to podcasters. With seating limited to 1,200 guests, the acts can be considered more on the intimate side so there shouldn’t be a bad seat in the house. You can also snag a drink (beer or wine) and some snacks before the show starts.

From classic New England fare to crafted cocktails, Boston is ideal for the traveler with an ambitious palate. Outside of the North End, which is a given for those coming to Boston with an appetite, there are plenty of other quality spots to consider. “When dining out in Boston, visitors can expect an amazing diversity of options,” says Jeremy Sewall, chef and co-owner of Row 34. “If you are here and want to experience the best of New England seafood, we have that. Looking for pizza that rivals NYC or Chicago? We have that. We also have fantastic restaurants in the surrounding neighborhoods and towns so don't be afraid to explore.” Sewall also adds that “Ten years ago, it felt like Boston had certain pockets of good food in certain neighborhoods—now no matter what neighborhood you are in, you won't be far from an incredible restaurant.”

10 am - Fill up at 3 Little Figs.
While we could recommend starting your day off the authentic New England way (a hot or iced coffee from Dunkin’), your travels deserve something a bit more sophisticated. Plus, Boston is home to a variety of stellar (and local) coffee chains, from Pavement Coffee to Thinking Cup. However, if you’re a real stickler when it comes to the perfect roast and breakfast treat, we highly recommend 3 Little Figs on Highland Ave in Somerville. You can get there by way of the Red Line, and spend the rest of your morning or afternoon exploring the shops around Porter or Davis Square.

1 pm - Eat and drink your way throughout Bow Market.
Union Square’s Bow Market, also in Somerville, is a food and drink lover's dream. The two-story, open-air market is home to more than 30 small businesses, with options like award-winning fries, poutine, and dipping sauces from Saus, or HOTBOX’s pizza and roast beef, the sister restaurant of the famed Mike & Patty’s, which also has a brick and mortar at Bow Market. You can also visit Remnant Brewing and wine bar Rebel Rebel before scoping out the different retail shops.

3 pm - Score a flight at Harpoon Beer Hall.
Boston’s craft brewery lineup is tough to choose from—there’s Sam Adams Brewery in Jamaica Plain with a taproom downtown, Trillium in Fort Point, Fenway and along the Greenway, Night Shift Brewing in Lovejoy Wharf, Lamplighter Brewing Co. in Cambridge—we could go on and on. But at the top of that list, we have Harpoon in Seaport. Its beer hall, open Monday through Sunday, has plenty of space and seating, and a solid list of seasonal and craft beers on tap. They also host live bands and some pretty fun events and festivals throughout the year, like their Octoberfest and Dogtoberfest in case you’re traveling with a furry friend.

6 pm - Dine at Row 34, a former Boston Wharf Company textile warehouse in Seaport.
There are plenty of great spots to indulge in a decadent meal around Boston, but Row 34’s menu, which offers a modern spin on fresh seafood married with comfort food, is a can’t-miss. Make sure to nab a reservation online as it tends to lean on the busier side. You’ll not only be amazed by the presentation of your meal (not to mention the exquisite raw bar), but the restaurant’s industrial vibe makes for an unforgettable and top-notch dining experience.

9 pm - End the evening with a signature margarita from Citrus & Salt. 
If you have room post-Row 34, then a night cap is calling your name. About a three-minute walk from the restaurant, you’ll find Citrus & Salt, which relocated from Back Bay to Seaport just this year. The coastal Mexican-inspired restaurant has signature cocktails, including the Citrus & Salt Margarita, which comes in flavors like prickly pear and passion fruit, or the C&S Mexican Mule.

The Verb Hotel ($)
Adjacent to Fenway Park you’ll find The Verb Hotel, a retro, rock 'n’ roll-themed boutique hotel. You can choose to stay within the hotel, or there are the 10 customer-crafted Backstage trailers inspired by life on the road. Regardless of where you end up sleeping, you’ll have access to amenities like their outdoor pool, open year-round, and each room (that includes Backstage) provides you with a record player and collection of vinyls to rock out to. Given the hotel’s location, you have your fair share of dining and drinking destinations, but we recommend, first and foremost, grabbing a bite to eat at Japanese tavern Hojoko, which is conveniently located right next to the hotel, followed by Fool’s Errand and Sweet Cheeks Q, founded by acclaimed Boston chef and restaurateur Tiffani Faison.

The Lenox Hotel ($$)
Located in Back Bay, the Lenox Hotel first opened its doors in 1900 after the hotelier and owner of New York’s Waldorf-Astoria set out to create one of the grandest hotels in Boston. Receiving its fair share of renovations throughout the years, the hotel’s sophisticated charm and elegant detail still shines, and with an optimal location, you can easily make your way around the city with stops along Newbury Street and over to the Charles River Esplanade. There’s also a chic cocktail bar, City Bar, conveniently located on the first floor of the hotel for late-night bites or drinks.

XV Beacon ($$$)
This luxurious boutique hotel, housed in a restored Beaux Arts building in Beacon Hill, features 63 rooms that are designed with the utmost attention to detail and opulence. Each room has its own fireplace, cashmere throws, heated towel racks, and more (and did we mention its dog-friendly?). If you’re looking for something divine and willing to splurge, XV Beacon (or 15 Beacon as guests call it) is where you’ll find your peace. Also, it’s prime real estate—surrounded by the historical neighborhood and only steps away from prominent points along the Freedom Trail, including Boston Common, Granary Burying Ground and Massachusetts State House.

How to get around
Boston is an extremely walkable city, but if you’re hopping around neighborhoods (think, the South End to Brookline) you may want to catch an Uber. The T (essentially the subway system) is also pretty dependable, and you can get to almost anywhere in and around the city by way of the Red, Green, Orange, or Blue line.

When to plan your visit
Boston really is a great destination year-round. In the spring, you can catch the blooms throughout the Boston Common and Public Garden. The summers are fun and rowdy with outdoor beer gardens opening up. The fall is, well, sublime given New England is known for its foliage. And in the winter, the city looks like it’s out of a Hallmark movie (probably because many have been based here). But if we had to choose, you can’t go wrong visiting at the end of August into October.

Do’s and don’ts when visiting Boston
Do: Pack walking shoes.
Don’t: Rent a car—parking is not only insanely expensive but spots are few and far between.
Do: Dine around town and make reservations
Don’t: Plan around happy hours—those don’t exist in Boston.

Your fun Boston dinner party fact
Marshmallow Fluff is said to have been invented in Somerville. To celebrate this revolutionary discovery, each year (going on its 19th year) the city puts on the beloved “What the Fluff” festival, featuring tastings, “Fluffy” merch, and games.

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