48 Hours in Boston

April 17, 2017

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Image by Jeff Gunn via Flickr Creative Commons.

No matter if you’re running in the Boston Marathon, cheering someone on, or visiting the Massachusetts capital for the first or fiftieth time, this American city is as close as you can get to Europe without flying overseas. It’s an insanely clean, breathtakingly gorgeous place where cobblestone streets, gas-lit lamps and intricate brownstone homes are the norm. It’s a place where everything is charming and historic, right down to the teensy ballpark that dates back to 1912.

Sure, there are some rowdy sports fans, some college kids and some lovable Boston attitudes: horn-beeping, smack-talking folks with beers in their hands and no “filtahs” on their mouths. But quintessential Bostonian traits aside, people here are incredibly multicultural and their diversity is reflected int he city’s many magical little shops and restaurants.

Spend 48 Hours here, and get hooked.

Day 1


Thinking Cup. Image by Brittany Fischer

9am: Copley Square, which is surrounded by three of Back Bay’s architectural treasures (Trinity Church, Boston Public Library and John Hancock Tower) is a good place to start your day. Power up with a tasty latte and almond croissant at Thinking Cup, Boston’s chicest coffee shop, a block away on Newbury Street.

10am: Walk up one more block and stroll along Commonwealth Avenue, letting your eyes feast on the nine beautiful blocks of Victorian brownstones. Be sure to ogle The Burrage House.

11:30am: From Massachusetts Avenue at the west end of the mall, make two lefts to return to Newbury Street. Boston’s most popular shopping district is as fun for people-watching as it is for depleting one’s funds – for something a bit different, check out the manly Ball and Buck.

1pm: If it’s Saturday, grab lunch at Casa Romero and savor the gorgeous subterranean setting as well as the margaritas and mole sauce. Any other day, swing by The Corner Tavern – they do a mean tortilla soup.

December Thieves. Image by Brittany Fischer.

3pm: Continue heading east as you window-shop and people-watch until you reach the picturesque Boston Public Gardens, a wonderland of flowers, swans, weeping willows and street musicians. Weather permitting, snap a picnic basket from Beacon Hill Bistro and set up camp in a quiet spot.

5pm: Walk down Charles Street for a brief tour of historic Beacon Hill and be sure to visit December Thieves and Crush Boutique if you’re in the market for a new outfit. Or, if you’d rather check out colonial neighborhoods, head toward Louisburg Square and Acorn Street.

6:30pm: Hop on the Red Line at the Charles/MGH T station and take it to Harvard Square. Grab a milkshake (call it a “frappé” to blend in with the locals) from Mr. Bartley’s Gourmet Burgers, and get to exploring Harvard’s regal campus and the shops surrounding it, like Grolier Poetry Book Shop.

8pm: A quick cab ride will bring you to North End for an Italian dinner. Try Giacomo’s Ristorante for the heartiest portions or Pizzeria Regina for wicked-good pies.

Modern Pastry. Image by Katherine Kimball.

9:30pm: Head to Mike’s Pastry and Modern Pastry, two rival bakeries located just steps away from one another. Try a cannoli from each and mentally vote for your winner in the legendary taste battle.

10pm: If you’re up for some laughs, see if you can catch a late comedy show on Hanover Street at Improv Asylum.


Day 2

10am: Start your morning right by treating yourself to a languorous brunch at Eastern Standard next to the Kenmore T station.

Bleacher Bar. Image by Eric Levin

12pm: Meander to Fenway Park. As America’s oldest ballpark, it’s worth of a tour – or savor the view from Bleacher Bar, which looks directly onto centerfield. To look the part, snag a cap at Yawkey Way Store beforehand.

1pm: If it’s the weekend, don’t leave the area without stopping by Island Creek Oyster Bar for one of their traditional lobster rolls – otherwise, consider coming back at 4pm (their weekday opening time).

Blackbird Doughnuts. Image by Brian Sacco.

2pm: For an additional treat, hail a cab and go to Blackbird Doughnuts in South End for a sweet treat and a cuppa. You’ll need the energy today!

2:30pm: Amble down pretty Tremont Street, darting in and out of the many eclectic shops. If it’s Sunday, be sure to check out SoWa Vintage Market: prime hunting grounds for antiques, art and snacks galore. Any other day, check out Follain for small-batch beauty products, Niche for urban garden products and Olives & Grace, a modern-day mercantile.

5pm: You’ll be thirsty now – and it’s 5 o’clock, so walk down Washington Street to the always lively Stella to get your party started. The signature drinks here are top notch, whether you opt for a basil lime gimlet or a watermelon Martini.

7pm: To help pad your stomach, head north to Back Bay (try taking the number 1 bus, which goes along Massachusetts Avenue, and get off at Hynes Convention Center) and order up some clam chowder at Atlantic Fish Co. Don’t forget the bread bowl.

9:30pm: Grab a nightcap a few blocks away at Lolita Cocina & Tequila Bar, a sultry subterranean spot with miraculously flattering, swanky red lighting.

Liberty Hotel. Image courtesy of the venue.

11pm: Night owls, hail a cab and head to The Liberty Hotel, a renovated, historic prison. Downstairs, you’ve got Alibi, a bustling bar and patio, and upstairs is Clink, a grand, stylish lounge that’s always buzzing with sophisticates.

1am: The T usually doesn’t stop running until after 2am, so you’ve got time to take the Red Line one station from Charles/MGH to Park Street, where you can soak up excess libations with a late-night burger at jm Curley and keep the night alive by slipping into the (no longer so secret) speakeasy in the back.

About the HUNT Boston Author: Brittany Fischer has beeen known to jump straight into a cab at the mere mention of an extraordinary meal, cocktial or shop. When asked what she majored in at Boston University, she deadpans, “Restaurants, coffee shops, bars and boutiques.” In addition to becoming a Boston aficionado, Brittany was actually studying journalism and her writing has since graced the pages of Boston’s most popular newspapers and magazines, as well as her blog, sheiswhosheis.com. In the rare event that she is not eating, caffeinating, drinking, shopping or writing, she’s on a long walk, wearing headphones and extremely impractical shoes, scouting out new places to go.

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