How to explore Boston in 48 hours

I imagine Boston will be smart, but smug. Earnest, and a little dull — a history lesson with literature thrown in. Cue the Boston Tea Party, MIT and Harvard, and Longfellow on that heroic midnight ride of Paul Revere.

I do not expect to get teary-eyed at a reenactment on board a gently bobbing boat. Or gasp with delight in front of a Jackson Pollock at the Harvard Art Museums. Or find myself singing Zombie by The Cranberries with a group of very cheerful drunks at an Irish bar.

How much of Boston can you see in 48 hours? I pull on my boots on a cold winter morning and set out in this elegant, alluringly walkable city to find out.

DAY ONE

8 am: Bagels at the Rowes Wharf Grille

I wake up early to drink in the view, along with a strong espresso shot. The Boston Harbor Hotel (Rowes Wharf) overlooks the harbour’s marina, and the sparkling water is speckled with boats. Breakfast is at the Rowes Wharf Grille, which, serves an average cappuccino but makes up for it with deliciously light bagels topped with curls of salmon and a bowl of cool, tangy cream cheese.

A historic ship docked at Boston Tea Party Museum
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10 am — Throwing chests overboard at Boston Tea Party Ships and Museum

As it turns out, I am a revolutionary at heart, if not a very important one. We are on board the Boston Tea Party Ships and Museum, and a feisty actor in a sweeping colonial-era gown, complete with a chequered apron and frilly bonnet, rouses visitors, recreating that historic December night in 1773.

In an unexpectedly moving performance, we boo and yell hurrah as an actor playing Samuel Adams shouts, “No taxation without representation.” The rebellion provoked British retaliation and pushed the American colonies onto the path to revolution. And for those of us who snoozed, at this museum we can participate in the act once more, heaving imitation tea chests overboard (while posing for cameras).

Unlike the revolutionaries, who had to melt into the anonymity of the night after this act, we can also sit down for a cup of tea afterwards. At Abigail’s Tea Room, also on board, you can sample the five blends thrown overboard that night.

The Samuel Adams statue in front of the Faneuil Hall building in the Faneuil Hall Plaza. Samuel Adams (1722-1803) was an American Patriot who helped organize the American Revolution, signed the Declaration of Independence, and became Governor of Massachusetts. The Custom House Tower is in the background.
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Try the New England clam chowder and end with a Boston cream pie in this charming, sunlit space. And if you need something stronger than tea, order a Rattle Skull cocktail, made with rum, whiskey and dark beer.

2 pm: Join the Freedom Trail walking tour

It is cold and windy beside the Samuel Adams statue in front of Faneuil Hall, once the meeting space of revolutionaries and now a gift shop bristling with coffee mugs, sweatshirts and soap. As we wait for the rest of the group, our tour guide from Boston By Foot (a non-profit educational organization committed to inspiring locals and visitors to discover the city), explains how the narrow roads, fringed by tall buildings, tend to funnel the wind, resulting in a cold that creeps past coats and mufflers.

Undeterred, we set out. In a bid to make peace with the past — and correct history, which, as always, is written by the victors — our guide explains how in 1625 this was the Shawmut Peninsula, known in the Algonquian language as “Mushauwomuk” (“the boat landing place”), and how its original inhabitants lost it to English settlers. Her stories bring the Revolution alive and explain how, ironically, Boston became known as the cradle of liberty.

Ornate interior steps and entrance of the historic Renaissance style architecture of the Boston public library in the Back Bay District neighbourhood of downtown Boston Massachusetts USA
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5pm: Catch up on your reading at Boston Public Library

Founded in 1848 and widely regarded as the first large free municipal library in the United States, Boston Public Library feels a bit like stepping into a scene from The Great Gatsby: Beaux-Arts drama, grand staircases, arched windows and carved stone lions.

I pull up a chair and catch up on email in Bates Hall, the hushed reading room, beside students sipping Starbucks as they work on their projects. With its soaring barrel-vaulted ceilings, retro green banker lamps set out in military rows, and shelves of leather-wrapped, gold-embossed books, the space encourages reading — something we can all do with in this age of endless distraction.

Bates Hall at the The Boston Public Library, a reading room that encourages you to focus
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7pm: Smoked rainbow trout at Chef Carl Dooley’s Mooncusser

The Michelin Guide finally launched in Boston, though it was surprisingly stingy with stars given how many remarkable restaurants the city is home to. We pick Mooncusser, a favourite with locals who are very proud of Chef Carl Dooley, a Cambridge native who uses local ingredients in surprisingly inventive ways, adding spices and techniques sourced from around the world. His food is precise and disciplined, while the space is fun and relaxed, with a comprehensive wine list.

Food at Mooncusser

I start with silky carrot soup spiced with guajillo chilli, and tuck into smoked rainbow trout, served with celery root, crispy tortilla and salsa verde.

After dinner, we check into XV Beacon on Beacon Hill, which takes us back a couple of centuries with its historic Federal-style row houses and narrow cobblestone streets. But more on that tomorrow.

The pet-friendly XV Beacon Hotel lobby
| Photo Credit:
Michelle Chaplow

DAY TWO

8am: Wake up at XV Beacon, and walk to Boston Common

Sure we geeked it up on day one with libraries, revolutions and history. Day two is when Boston unbuttons its collar and kicks off its shoes. I luxuriate in room service for breakfast: creamy Greek yoghurt topped with fresh berries, goji berries, chia seeds, toasted oats and hemp. I pair it with an unexpectedly delicious Green Monster smoothie, packed with kale, spinach, pineapple, banana, almond milk and flaxseed.

If you are an early riser, walk across to Boston Common, where the colonial militia once mustered for the Revolution. It continues to be a space for free speech and public assembly. Also, ideal for a picnic.

A couple at Boston Common, the public park in Boston, Ma.
| Photo Credit:
Liz Leyden

11am: Get close to a Pollock at Harvard Art Museums

The Harvard Art Museums are relatively compact, so you never feel overwhelmed, and yet some of the biggest names in art hang casually side by side, making every turn a surprise.

Best of all, there are no crowds — the busiest part of the museum seems to be Jenny’s Café, where students gather over cappuccinos. I spot works by Jackson Pollock, Mark Rothko, Paul Cézanne, Vincent van Gogh, Claude Monet and Pablo Picasso. As I move from room to room, Modernism unfolds like a relaxed art class, with students setting up easels to sketch directly in front of the paintings.

On the top floor, I pause at large glass windows that look into sunlit conservation studios, where art is being painstakingly restored by students, all bent over centuries-old surfaces with magnifying lenses, cotton swabs and brushes.

Students sketching at the Harvard Art Museums
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Shonali Muthalaly

1 pm: Lunch and purple prose at Lovestruck Books

We drop by Lovestruck Books at Harvard Square, a romance bookstore with a wine bar, an unabashedly pink couch and lip-shaped cushions. I browse books with names like Polyamorous Advice by Sam Cat, The Einstein of Sex by Daniel Brook and What to Do When You Get Dumped.

The categories are impressive: Romantasy, Paranormal Romance, Sports Romance and Contemporary Romance. You can also choose a ‘blind date’ and buy a book wrapped in brown paper — which may prove better than your last Tinder date.

Have lunch while you read Baby-Making for Everyone: a bacon, egg and cheese sandwich paired with either their iced Red Eye (iced coffee with a double shot of espresso) or a glass of Bruto & The Beast 2021 by Valli Unite from Piedmont, which Sophie, the bartender, describes as “an existential, Kafka-reading type who’s effortlessly cool.” (I would date him.)

Visitors to the Harvard Yard, the oldest part of the Harvard University campus in Cambridge, Massachusetts, wait in line to take photos with the John Harvard Statue
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hapabapa

4 pm: Behind the scenes with a student at Harvard University

Ashmit Singh, an intimidatingly brilliant student at Harvard University, shows us around the campus. Student-led Cambridge-based Trademark Tours tours are a fun way to peek into everyday life at some of the world’s most prestigious universities, Harvard and MIT. Ashmit takes us through Harvard Yard, Memorial Hall and to the John Harvard statue, where we rub his boot for good luck — which usually reportedly translates to academic success and Ivy-League-adjacent admission miracles. (I am still waiting by my mailbox.)

We pause at Lowell House, where Matt Damon and Natalie Portman once lived, and then Ashmit takes us past the Final Clubs, including Spee, which counts John F Kennedy among its members. (A Final Club is a private, invitation-only social club at Harvard — part dining society, part networking space and, from the sound of it, home to some outstanding parties.)

We walk past an Indian food truck blasting Diljit Dosanjh, reportedly famous for its samosa chaat, and stand in front of the Brutalist Science Center, which came up in the 1970s. Ashmit quotes former Harvard president Abbott Lawrence Lowell: “A well-educated man must know a little bit of everything and one thing well.” He adds, “So there are four areas you have to take classes in: arts, humanities, ethics and civics.” His own subjects include the science of sleep, the art of Armenia and Chinese philosophy.

7pm: Dinner and a performance at Grace by Nia

Grace by Nia is delightfully over the top: chandeliers dripping golden light, velvet curtains in gold and orange, and ornate pillars. The hum of conversation is punctuated by cocktail shakers, and the floor is sticky with fruit juice and beer. A modern-day supper club, the space has an intimate stage for live music. The band is playing Minnie Riperton’s Loving You from the early Seventies.

Our waiter is Colombian, and as the band launches into Chris Brown, we order from a menu focussed on Southern cooking. We eat crab cakes and fried Louisiana catfish with buttermilk batter and Cajun remoulade. The music is the point here, so do not have high expectations of the food or cocktails — both are okay.

9 pm to dawn: We party Boston-style

There is a patient, seemingly never-ending line of trendy hipsters in sparkly tops and miniskirts outside Carrie Nation Cocktail Club, next door to our hotel, XV Beacon. Named after an anti-booze crusader who reportedly walked into bars “with a hatchet in hand and the Lord at her side.” She would hate this flapper-era bar, where people party hard on weekends — not that anyone seems to care.

It is far too cold to wait in line for hours. And I have outgrown nights that begin with lipstick, optimism and tequila shots, then end with paracetamol and regret. We head to the cosy Emmett’s Irish Pub next door instead, where we get carded (much to our delight) by the grouchy doorman.

Inside, we fall in with a loud, raucous group knocking back pints of draft beer and singing together like a spirited — if occasionally off-key — choir.

I scan the menu. The most popular beer is called Sam Adams. Of course it is.

In a city that built its identity on rebellion, it feels only right to raise a glass to freedom.