History and intellectualism meet in Boston, where Puritan roots and events of the American Revolution have given way to a city that houses more than its fair share of universities, bookstores, and coffee shops. As a local, I’ve also noticed a hint of revolutionary spirit remains in the hardy hearts of Bostonians as the neighborhoods continue to evolve.
But you’d be mistaken to suggest Massachusetts’s capital has left the past behind. Historic churches, burial grounds, and cobbled streets lend a colonial charm to the city, where the famed Freedom Trail walking path winds from the leafy Boston Common park, through the old North End neighborhood, to the Bunker Hill Monument in waterfront Charlestown.
Beyond the historical lure, you’ll find up and coming neighborhoods like the Seaport, where the Institute of Contemporary Art presides over sleek new bars and eateries that draw nighttime crowds. And an air of innovation hovers across the Charles River in Cambridge, home to Harvard, MIT, and all the student haunts that accompany them. Whether you’re looking to the past or the future, you’ll find it in a few days in Boston.
The North End’s spirit is most visible in independent shops like Shake the Tree.
Courtesy of Shake the Tree
Day 1: Stroll through a 1600s park and eat a timeless Italian cannoli
Marian Klausner, owner of North End gift shop Shake the Tree, describes Boston as a “very walkable city.” If ever distances are too far to take on by foot, the public transit system (known to locals as the “T”) is how most people get around. It’s possible to drive, but the infamously aggressive traffic and confusing tangle of streets make it more peaceful to meander as a pedestrian.
Start your first day of walking at the Boston Public Library in Copley Square. The McKim building has served as the library headquarters since 1895, and features murals by the likes of John Singer Sargent and Edwin Austin Abbey. Stroll through the iconic Bates Hall reading room and step into the peaceful courtyard designed to mimic that of a 16th-century Roman palazzo. Stop by the library’s tea room for a steaming cup before you go; if you want to return later, the establishment is known for its tea-infused cocktails.
Exit the library and head to Newbury Street, a mile-long road lined with shops inside brownstone buildings, from Chanel to H&M and independent boutiques like Milk Money. Be sure to check out Trident Booksellers & Café for cheddar cheese–stuffed giant tater tots, and take a peek at the street’s myriad art galleries like Pucker and Sitka Home.
When you’re all shopped out, stop by Saltie Girl for a seafood lunch, including tins of sardines or salmon as well as a particularly excellent hot or cold lobster roll (which you must order at least once while you’re in Boston). From here, you’ll be close to the Public Garden. The Victorian park was the first public botanical garden in the country and brims with plants, fountains, statues, and a scenic lagoon where swan boats float in the summer. Afterwards, cross Charles Street to the Boston Common, the city’s main central park and the oldest park in the USA, created in 1634. In the winter, Frog Pond at the heart of the Common turns into an ice skating rink.
It’s about a 20-minute walk from the Common to the North End neighborhood (or to give your feet a break, hop on the T to the Haymarket stop). The North End is Boston’s Little Italy and the city’s oldest residential community, home to colonial sights like Paul Revere’s House and Old North Church. It’s best experienced by wandering—and by eating—but check out the feast schedule if you visit in the summer and want to catch one of the neighborhood’s elaborate celebrations.
“The North End is filled with mom-and-pop Italian restaurants and small food shops selling Italian pastries, gelato, cheeses, meats, olives, and groceries,” says Klausner. Stop by Parziale’s Bakery, which Klausner describes as the “best-kept secret” for amazing pizza. While Mike’s Pastry and Modern Pastry have lines out the door, they’re worth the wait for dozens of flavors of cannolis and lobster tail pastries. Swing by Salumeria Italiana, too—“It’s my favorite place to buy cheese and meats,” says Klausner.
For dinner, head to Tony & Elaine’s for an old-school vibe, complete with red checkered tablecloths. “The meatballs are a must,” says Klausner. Finally, end your night at Parla. There’s an extensive drink menu to choose from, but opt instead to roll a 20-sided dice to let fate choose an original off-menu cocktail.
Harvard Square has been filled with bookstores for 100 years, but there’s room for newcomers like Lovestruck Books.
Courtesy of Lovestruck Books
Day 2: Soak up views of the Charles River and get bookish in Cambridge
It’s hard to say which of Boston’s neighborhoods is the most historically beautiful, but Beacon Hill makes a strong case, overlooking the city from atop a lantern-lit hill. Bop around the boutique shops on Charles Street selling everything from vintage handbags to eclectic home decor, and duck into Beacon Hill Books & Cafe for warm chai oatmeal or a cup of coffee and a browse. Then make your way west to stroll the Charles River Esplanade, a scenic green space along the water. When you’ve had your fill, traverse the pedestrian walkway of the Longfellow Bridge, stopping to admire the river and the skyline. Get on the red line of the T at Kendall Square and ride two stops to Harvard Square in Cambridge.
“Cambridge seamlessly blends the old and the new, creating a unique mix of culture, history, arts, and education unlike anywhere else,” says Rachel Kanter, owner of Harvard Square’s Lovestruck Books. Once you’ve arrived, get a chicken pesto sandwich at Cardullo’s and eat outside on one of the square’s many benches—or in Harvard Yard, if you fancy a closer look at the famed university. You can wander the university campus before thoroughly investigating Harvard Square’s many bookstores: There’s the Harvard Coop if you want some Harvard University merch alongside your literature; the Harvard Bookstore, an independent bookseller that’s been around since 1932; Grolier Poetry Book Shop, a poetry-specific store founded in 1927; and Rodney’s Bookstore, which sells used and rare books. Kanter’s bookstore, a more recent addition to the square, focuses on romance reads.
Check out other businesses in the square (Kanter recommends the lingerie boutique Forty Winks, “a perfect pairing to go along with a new romance novel”), then walk 20 minutes or take the subway one stop to Central Square for dinner at Vietnamese fusion joint Saigon Babylon. Here you’ll find jungle plants and stone statues, a roofdeck overlooking Lafayette Square, and dishes like oxtail with rice noodles. For dessert, walk over to vegetarian diner Veggie Galaxy for a vegan coconut-based frappé, from mocha to Oreo flavored.
If you’ve still got some energy left, wander into Roxy’s. It’s a grilled cheese restaurant, but you’re not there to eat; instead, walk to the back for a speakeasy-style, adults-only arcade hidden inside. Order up a tiki-style cocktail and try your hand at some nostalgic games.
Don’t miss the ICA’s secondary outpost, reachable by boat.
Photo by Wangkun Jia/Shutterstock
Day 3: Get a close look at Boston’s vibrant art scene, from SoWa to the ICA
Begin your day with brunch at Beehive, a Bohemian restaurant serving shakshuka along with live jazz in the culturally rich South End neighborhood. The Boston Center for the Arts next door hosts various events and exhibitions, so check the calendar to see if anything’s on while you’re nearby. Then walk about 10 minutes to the SoWa neighborhood, known for being a funky arts district. On Sundays, in addition to open artist studios at 450 Harrison Avenue, the area hosts the SoWa Open Market May through October, with stalls selling art and farmers’ produce. On any day of the week, the area has a slew of art galleries to explore.
Hop on the silver line to make your way to the Seaport, a South Boston waterfront neighborhood that has been redeveloped over recent years. Your first stop should be the Institute of Contemporary Art (ICA), originally founded in the 1930s; it moved to its current location in 2006. In addition to wandering amid rotating exhibits from established and emerging contemporary artists, enjoy the view of the harbor through the building’s massive windows. In the summer, you can catch a boat to the ICA Watershed in East Boston to take in a rotating exhibition from artists like Hew Locke and Guadalupe Maravilla. The Seaport is also home to the Boston Children’s Museum, unmistakable with its giant milk bottle out front.
Afterwards, stroll along the water on the Boston Harborwalk (with a stop at the site of the Boston Tea Party), followed by a wealth of options for dinner. Choose from modern steakhouse Mooo, glitzy Chinese restaurant Mr. H, and the supremely fun Grace by Nia, where live music accompanies dishes like fried chicken and biscuits or oxtail and grits. For postdinner drinks, Marcelino’s has moody decor and sweet baklava-spiced cocktails.
As a hub for universities and students, Boston offers multicultural restaurants, like Venetian plates at SRV.
Courtesy of SRV
Day 4: Investigate a museum heist and hear ground-breaking live music
Spend the morning exploring the Isabella Stewart Gardner Museum, housed in a stunning, mansion-like space—and the only one of Boston’s world-class museums that’s best known for an art heist. In 1990, two thieves stole several well-known works (including a Vermeer and Rembrandt), and the museum is still searching for the missing paintings. As you browse, you’ll spy the empty frames of the stolen artwork. But while the art (both missing and otherwise) is the museum’s primary draw, the flower-filled courtyard at its heart is worth some serious lingering.
Enjoy a lunch of maple-roasted squash with burrata or gochujang chicken bao at the excellent museum café before heading out for a walk. Across the street from the museum is the Back Bay Fens, part of Boston’s Emerald Necklace, a network of green spaces designed by Frederick Law Olmsted. Check out the fragrant Kelleher Rose Garden and the rambling Fenway Victory Gardens, originally planted by citizens in 1941 as a source of food during World War II. Baseball fans will want to veer northwest toward iconic Fenway Park, which offers tours, while in the neighborhood.
Not far from the Fens, the Christian Science Plaza is home to one of Boston’s lesser-known wonders, the Mapparium. You can enter this three-story-high stained glass globe dating back to the 1930s, and visitors are typically as enchanted by the strange acoustics as they are by the visuals. To visit, buy a tour ticket at 210 Massachusetts Avenue.
For dinner, SRV has Venetian-inspired small plates like tuna crudo and beet risotto, while Lucy’s Ethiopian Café & Restaurant serves up platters of spicy red lentil misir wot alongside spongy injera in a casual setting. Then it’s time to take in your choice of musical performance. Built in 1900, Symphony Hall is a National Historic Landmark where audiences can enjoy performances from two orchestras—the Boston Symphony Orchestra and the Boston Pops—along with other concerts and events on its calendar. For a more low-key vibe, walk over to Wally’s Café Jazz Club. The legendary venue has been around since 1947, and in the years since, has hosted performances by the likes of Billie Holiday, Charlie Parker, and Dizzy Gillespie. The club’s location near a few of Boston’s music schools keeps the talent fresh; you can buy tickets for nightly performances online or at the door.
In addition to boutique decor, Newbury Boston has a prime location in the heart of the city.
Courtesy of Newbury Boston
Where to stay
With a prime location directly across from the Public Garden, the Newbury Boston is a stylish choice, with wood-burning fireplaces inside the suites and impressive art pieces scattered around the property. Back Bay’s Mandarin Oriental is elegant and luxurious, and conveniently connected to the shopping mall at the Prudential Center. Its award-winning spa is well equipped with a vitality pool and crystal steam room, and the on-site restaurant, Ramsay’s Kitchen by Gordon Ramsay, serves such signature dishes as beef Wellington and chickpea tikka masala. For a funky, modern stay in the South End, opt for a loft or suite at the Revolution Hotel, which have the feel of private apartments with kitchenettes.
