All Articles 3 perfect days in Boston

3 perfect days in Boston

Joanna Rakoff
By Joanna Rakoff11 Apr 2024 11 minutes read
A statue of George Washington on horseback surrounded by greenery and buildings in the background.
George Washington Statue, Boston Public Garden, Boston, Massachusetts.
Image: joe daniel price/Getty Images

Don't bother comparing Boston to NYC or Chicago, my hometown has its own thing going on. Most travelers visit for a deep lesson on American history, to walk the gracious, tree-lined avenues, and to eat its irresistible clam shack cuisine. But in the past decade New England's largest city has transformed from a quiet, ultra-traditional college town into a sophisticated destination for inventive dining, cutting-edge art, and so much more.

It's impossible to see all of Boston in three days. The city is spread out across twenty three neighborhoods and packed with historic sites, museums, restaurants, and shops. But this weekend itinerary is a start: These are all places that my family loves (some are well-known tourist spots, and others are deeply off-the-beaten-path), with plenty of recs from Tripadvisor users, too.


DAY ONE

A brick-walled dining room with metal stools.
Dining area at Select Oyster Bar, in Boston.
Image: Harvard Square, Brattle Street, Cambridge, Massachusetts

MORNING: Walk in the footsteps of the founding fathers

Boston is a grab-and-go kind of city when it comes to breakfast. It's filled with local bakery chains like Flour, Tatte and Blackbird Doughnuts, but lacks bacon-and-egg joints.

Start your day at Blackbird's Beacon Hill outpost on Cambridge Street with one of their ever-changing seasonal creations and a coffee, then sip as you stroll the block or so to Charles Street, the neighborhood's main drag. With its cobblestone streets, brick sidewalks, gas street lamps, and Victorian row houses, Charles Street looks like a city from a different era, and walking down it, popping into the many charming shops with their leaded glass windows, is an experience unto itself.

Don't miss the museum-like Beacon Hill Books and Cafe, which has a vast selection of books arranged in rooms that resemble a cozy Edwardian home. Anyone interested in fashion should save time for Ouimillie, a local boutique devoted to indie designers, and Covet, a resale shop stocked with the castoffs of Beacon Hill's well-appointed residents. Make sure to detour onto the side streets. Tiny Acorn Street is a major crowd-pleaser.

Once you've acclimated to your quaint surroundings, delve deeper into the real history of the area with a visit to one of the 18th and 19th-century buildings. Explore on your own by visiting one of Boston's perfectly preserved home museums, like Nichols House, home of suffragette Rose Standish Nichols; the Museum of African American History, housed in the country's oldest black church; and the Park Street Church, a locus of the abolitionist movement (Harriet Beecher Stowe's brother served as pastor in the 1820s and '30s).

Travelers say: "​​From the meeting house turned Belknap Street Church—the first church exclusively for African Americans in Boston—to the first public school for African Americans in the nation, this is living history. There is no better place to invest an hour and a half of your time that will enrich your life." –@EliasMcC

GREAT OPTIONS FOR FREEDOM TRAIL GUIDED TOURS

  • If you want to gain an understanding of Boston history, consider putting yourself in the hands of an expert, like those at the top-rated Hub Town Tours, and taking a guided tour of the Freedom Trail.
  • Group tours can last up to two hours, which can be too much (trust me) for kids younger than ten. Families with younger kids or those who want a shorter tour should consider a private tour geared toward your family's interests and stamina. Authentic Revolutionary Boston offers such tours, led by guides in period dress, which lend themselves well to kids.
  • Or try an Old-Time Trolley Tour, which will give you history and an extensive overview of the city. You can hop on or off at stops throughout Boston.

AFTERNOON: Grassy fields and grand boulevards in Back Bay

Before you head into Boston Common—the first stop on any sojourn in Back Bay—pop into The Upper Crust pizzeria and grab a few slices to eat in the park.

Take your time wandering around the Common, making sure to visit the Frog Pond—open for public skating in the winter and wading in the summer—and take a spin on the carousel. If you have kids in tow, definitely stop at the Tadpole Playground, where my little ones could spend an entire day.

Then, head across the street to the Public Garden, which is familiar to many as the setting of Make Way for Ducklings. There are sweet bronze statues of the ducklings, and kids love to hop on and off them. In the warmer months, get in line for a swan boat ride; the long wait is worth it.

Walk out the southwest corner of the garden and head west along Boylston Street, stopping at Copley Square, the sizable European-style plaza at the city's heart. Then, head into the Boston Public Library and consider signing up for one of the BPL's tours or just wandering around, making sure to check out the Sargent murals. You can also refuel at the stately The Courtyard Tearoom. It's one of Boston's best-kept secrets.

Now it's time to put history aside and do what Bostonians do when they come to Back Bay: Shop. Newbury Street is the city's main shopping thoroughfare. On its east end, you'll find global luxury shops like Chanel and Akris, as well as local, spots like Alan Blizerian, which stocks an array of less mainstream designers. As you walk west, you'll find more accessible shops, like Opal & Oak, a favorite of Boston teens, and Revolve, a well-curated consignment shop, along with many other local boutiques and national brands.

EVENING: Classic Boston cuisine redux

Back Bay is filled with great restaurants of every imaginable stripe. Still, it's your first night in Boston, so let's get you some seafood at Little Whale, an adorable and elegant take on the classic clam shack, which offers all the classics—lobster rolls, fried clams, bluefish dip—but plenty of 21st-century dishes, too. Sit outside if you can: The people-watching on Newbury Street is seriously fun. Also excellent, but pricier, Select Oyster Bar and Saltie Girl. If you didn't snag a reservation or want something more casual, grab tacos at La Neta, Greek sausage at GreCo, or ramen at Red White.

Worthy detours along the way

DAY TWO

A street in Cambridge, lined in street lamps and signs.
Harvard Square, Brattle Street, Cambridge, Massachusetts.
Image: APCortizasJr/Getty Images

MORNING: Inside the Ivy League

Start your day at Faro, a cozy, plant-filled cafe on tiny Arrow Street, a favorite of locals. If you need a more robust meal after all the walking yesterday, head to Tatte, a sunny, two-story French-Israeli cafe with delicious shakshuka and egg sandwiches. (Tip: Sit on the more quiet second floor.) Now it's time for the main attraction. Stroll around the corner to Harvard's Visitor Center to meet the student leading your campus tour (you'll need to sign up in advance). These free tours give you a feel for the beautiful campus and the school's history. They're also long and primarily outside, so make sure you're dressed for the weather.

You're going to need a little rest afterward. If it's nice out, plop down in one of the Adirondack chairs that dot Harvard's green spaces and engage in some serious people-watching. If it's dreary out, head across the street (Massachusetts Avenue, but pretend to be a local and call it "Mass Ave") to browse the incredible selection at the Harvard Bookstore. Tip: The basement is filled with used books in fantastic condition at a fraction of the cost of new ones; it's an excellent source for kids' books, particularly.

MORE TOUR OPTIONS

  • If Harvard's official tours are filled up–and they can be–but you'd still love to traverse the campus with a student guide, reserve a spot with The Hahvahd Tours.
  • Experience Cambridge like a local by taking a bicycle tour.
  • Interested in touring MIT, as well? Book a campus tour.

AFTERNOON: Charming shops and secret museums

If you didn't hit Tatte for breakfast, head there for a salad nicoise (my favorite), a tartine (open-faced sandwich), or that famous shakshuka. A more traditional Cambridge option would be Mr. Bartley's, which has justifiably loved burgers, with a mind-boggling array of toppings and great fries.

On weekends, Harvard Square fills up with off-duty students and teens from all over the Boston area, partly due to the fun vibe but mostly because of the many cute shops. If that's your thing, wander for an hour (or three). Start with The Attic, a well-curated and very inexpensive vintage shop just off Mass Ave (don't miss the $5 and $10 bins, which hold serious treasures), then head to Mint Julep, on picturesque Brattle Street, which is packed with colorful women's clothing at all price points and in every style imaginable (the second floor is all sale items).

You can't visit Cambridge without stopping at L.A. Burdick, a Viennese-style chocolatier known for their hot chocolate and decadent pastries. Kids love the chocolate mice. And their premade sets, in reusable wooden boxes, make perfect gifts.

Now it's time for a little Choose-Your-Own-Adventure. If you want to keep browsing, head down Mass Ave. toward Central Square, the younger, funkier cousin of Harvard Square, where you'll find a vintage shopping paradise. On Mass Ave, there's Cheapo Records, which sells much more than music (check out the concert tees in the back) and two enormous charity shops (Boomerangs and Goodwill). Around the corner, on Columbia Street, is Found, which encompasses three storefronts and has everything from streetwear to couture. And if this still isn't enough, walk over to The Garment District, a legendary vintage warehouse on Portland Street.

If you've had enough shopping, make your way to Boston's best-kept secret: Harvard's museums. Adults and teens should head to the Harvard Art Museums, which has a collection that rivals the world's best, including beautiful Sargents and Whistlers and a vast wing devoted to ancient Chinese art. If you're traveling with kids, head to the fun, interactive Harvard Museum of Natural History, with its huge dinosaur skeletons. Don't skip the gem and rock room (trust me) or the glass flowers.

Travelers say: "Overall a great museum with a smaller collection on display than other art museums but the art is outstanding and beautifully displayed. I rate this museum much higher than the Boston Museum of Art as the layout, the curatorial display, lighting and quality of artwork represented surpasses in the overall visitor experience....and the admission is free!" –@NYCtravelexplorer

EVENING: Old movies and comfort food

Check out what's playing at the Brattle Theatre, a loved repertory theater, which on any given night could be playing a new release or, say, a Hitchcock film. Then grab a bite next door at Alden & Harlow, a comfortable—but elegant—bistro equally suited to an early supper with kids, a solo meal with a book, or a romantic dinner. If you're exhausted and want something quick, try Felipe's, a fantastic taco place.

In Central Square, Cicada is my favorite restaurant in Cambridge. It's casual and serves Vietnamese-style bowls of rice noodles, black rice topped with baked salmon, and many other dreamy dishes. (Don't miss the hibiscus iced tea)

Worthy detours along the way

DAY THREE

The red-and-green exterior of Fenway Park.
Facade of Fenway Park, in Boston.
Image: stecks05/Getty Images

MORNING: A miniature earth and a massive stadium

Start the day at another much-loved Boston bakery: Flour, which has branches throughout the city. Today, you're heading to the Dalton Street outpost. Go for a breakfast sandwich or a moist, crumbly muffin (gluten-free and vegan options available), and stroll to The Mapparium. A three-story glowing model of the earth, which you traverse on a glass bridge, the Mapparium is amazing visually. But the best thing about it is the acoustics: Stand at the center and yell, and your voice bounces back to you. Stand on one end of the bridge, whisper, and anyone at the other end can hear you as clearly as if you were speaking directly into their ear. (Entry is timed, and I highly recommend buying tickets in advance)

Next, walk over to a little ball field you may have heard of Fenway Park. Even if you're not a baseball fan, you'll want to tour the stadium and learn about its rich and complex history. The physical stadium is beautiful and offers fantastic views from the Green Monster wall.

Travelers say: "Coming from Scotland with no real interest in baseball, I wasn't sure how much I would enjoy this tour. What can I say…. It was a fantastic experience from start to finish. The history of the place is unreal, and our tour guide, Meredith, was absolutely incredible. Her knowledge about the stadium and the Red Sox was second to none, and her interaction with the audience was brilliant. Well worth the money and a must-do for anyone visiting Boston." – @psg1974

MORE TOUR OPTIONS

AFTERNOON: Green space and art

When Bostonians say "Fenway," they might be referring to the park, but they're likely talking about the actual student-heavy neighborhood surrounding it. Set off down Jersey Street, through the heart of the area and the lovely bottom half of The Fens nature reserve. At the end, you'll find yourself in front of a grand mansion: The Isabella Stewart Gardner Museum. Before you venture into the house itself, eat lunch in the hushed, luxurious lobby café, a more elevated experience than your typical museum cafeteria. Tables are generally easy to come by, even on the busiest days.

Now it's time to explore the Gardner, a museum like no other in the world, no exaggeration. An obsessive collector of art, Gardner built this home to house her collection, and the structure itself—with its lushly landscaped courtyard—is as much the draw as the art inside. Give yourself about two hours here.

EVENING

If you still have some juice left, and it's before five, consider taking a cab to the New England Aquarium, which is often quiet in its final hour as families head home for dinner. If you're visiting in the summer, consider taking a pre-dinner ride on Codzilla, a high-speed boat adored by local kids and teens. (Hop on right next to the aquarium.)

Grab a cocktail or a superb Michelada at Borrachito, a taqueria where the cocktail bar is hidden behind what looks like a walk-in freezer door.

And for dinner, try the seasonal Mediterranean-style menu at Chickadee or walk over to the North End—you're just a few minutes away—and grab a pie at the (justifiably) legendary Regina Pizzeria.

Know before you go


Boston can be brutally cold in the winter. You'll be fine if you're visiting primarily for Boston's museums—the Gardner, the MFA, the ICA, etc. But if you're hoping to shlep around the city, partaking of historic sites, you might be miserable between December and early May.

Spring in Boston is beautiful, as is the fall, when the trees turn brilliantly red and orange. In summer, crowds descend on Boston, and popular attractions can be truly mobbed.

But if you don't mind longer lines, or if you're an excellent planner able to procure tickets for everything far in advance, the summer is a fun time to visit.

You might want to check out school calendars before you make travel plans, as certain significant events will jack up hotel prices and cause congestion everywhere.



In general, it doesn't really matter which day you land in Boston. Popular tourist attractions tend to be open every day. Some smaller sites are only open for extended weekend hours.



Boston is not New York. Restaurants tend to close at 9 p.m., especially on Beacon Hill, and shops close on the earlier side, so plan accordingly. In more student-heavy areas–Harvard Square, Davis Square, Fenway–you'll find restaurants that stay open later. And due to Boston's inexplicable ice cream obsession, you can generally find a parlor open later than any other business nearby.



Here are the four neighborhoods I recommend to friends when they ask me where to stay. The first two are historic, classic Boston neighborhoods, with gracious buildings and an old world feel, in the heart of everything; the second two are more recently developed areas, with brand new hotels and restaurants, which have an exciting vibrancy to them:

Back Bay: The grand dame of Boston neighborhoods is chock full of shops and restaurants and is surrounded by historic sites. This is your best bet if you're excited to explore historic Boston. For a super-luxe choice I recommend The Newbury. For a more affordable option, The Sheraton. For a super central location: The Lenox. But don't stress over this. Any hotel in this area is going to be great.

Harvard Square: Charming and cozy, the Square is a bit like staying in a small, colonial town plunked down in a city. The Charles Hotel is luxurious, with spacious rooms, views of the river, and great restaurants. More affordable is Hotel Veritas, in a beautiful, quirky Victorian mini-mansion.

Kendall Square: When tech came to Cambridge it transformed this neighborhood into a vibrant hub with great restaurants, the city's best movie theater, a kayak and canoe launch, a popular outdoor skating rink, and so much more—all a short walk across the bridge to Back Bay and the rest of Boston. I like Le Meridien Boston, which also offers access to the super-fun Central Square, which has its own great shops and restaurants, but the Kendall Hotel, in an old firehouse, is gorgeous, and the Mariott is centrally located and good for families.

The Seaport: Boston's newest neighborhood has an unparalleled vibrancy and youthful vibe, and it also has some of the city's best hotels. The Marriott Residence Inn, with its sunlit atrium, huge, comfortable lobby, and industrial-chic decor, is a great choice. The Boston Harbor Hotel and the Omni are fancier, but also excellent choices.


Joanna Rakoff
Joanna Rakoff is the author of the novel "A Fortunate Age", winner of the Goldberg Prize and the Elle Readers Prize, and the bestselling memoir "My Salinger Year". She's written for Vogue, The Atlantic, the New York Times, and many other publications. The film adaptation of "My Salinger Year", starring Sigourney Weaver and Margaret Qualley, is currently streaming. Rakoff's new memoir, "The Fifth Passenger", will be out in 2025. You can find her on Instagram @joannarakoff.