24 Hours in Boston

Bean town, college town, town that the Red Sox call home; Boston, unlike anywhere else in the wonderful US of A, has uniquely deep-rooted identifiers. From slinging seafood dishes like clam chowda’, to calling themselves ‘massholes’ (it’s a thing, look it up), piercing into Boston’s underbelly as an outsider, or even sometimes as a local, can pose quite the challenge. And while on the surface Boston may seem easy to navigate, it’s definitely worth digging a little deeper.

Since we’re nice people an all, we thought we’d help you do just that. In just 24-hours, here’s our take on how to break into the best of Boston, plus a map to help you get there.

12PM: BIG FLAVOR

Mike and Patty’s tiny sandwich shop tucked away in Bay Village is jam-packed with big flavors, our top pick is the Baller Sandwich.

1PM: BUTTER ME UP

Impress a lunch date with a delicious wild mushroom baguette and butterscotch scones at the always charming South End Buttery Cafe.

2PM: ON THE MARKET

Open on weekends only, uncover the local art scene and support small businesses and entrepreneurs at the buzzy SOWA Market.

Photo via SOWA Market Facebook

3PM: NOT WHAT IT SEEMS

Walk to the back of Bodega, trigger a tile in the floor, and watch as the Snapple machine slides away to reveal a sleek shoe store.

4PM: SHHHH!

A sacred local secret is that 3 hours before a Fenway game, you can see the players up close and personal during practice on the Fenway Batting Practice Tour.

5PM: GOING UP?

Discover the secret urban oasis at the rooftop of 4 Cambridge Center, where in-the-know locals go to be surrounded trees, greenery, and a community vegetable garden.

6PM: IT’S BEEN TRILL

Keep it real with a local IPA at Boston’s first open-air beer garden, Trillium Brewing Company, founded by a self-proclaimed beer geek and botany nerd who call themselves ‘a young dumb couple in love.’

7PM: KENNEDY STYLE

Sit in the very same booth JFK once frequented at the Union Oyster House, and enjoy a classic New England clam chowda’ and Boston baked beans.

Union Oyster House via@jayjayhonasan

8PM: BUILD-A-BOIL

You don’t know local seafood until you build-a-boil at Bootleg Special. Don’t let exteriors fool you, the swanky underground spot is a must.

9PM: PARTY IN YOUR MOUTH

You’re in Boston, which means you pretty much have no other choice but to give in to your carb cravings. Feed your next one with a Cannoli at Mike’s Pastry in the North End. 

10PM: APHRODISIACS FOR DINNER

Set the tone for a spontaneous night ahead at Island Creek Oyster Bar, the Lobster Roe Noodles and Oyster Sliders are notorious aphrodisiacs.

11PM: GO WITH THE FLOW

Keep up with the locals and down another drink at Parla, a speakeasy-inspired Italian joint with a killer Bee-sting Julep.

12AM: IT’S SATURDAY NIGHT!

The Coolidge Corner Theater throws a ‘Saturday After Midnite’ series, transforming the Art Deco venue into a hub for alternative hankerings.

Coolidge Corner Theatre via @kenechukwu.jpg

1AM: AND ALL THAT JAZZ

Wally’s Café is among the oldest family owned and operated jazz clubs in the entire United States, they’ve been serving up live music and libations since 1947.

2AM: MEANT TO BEE

Tucked in a secret boiler room in the Boston Center for The Arts Complex, The Beehive is a boho bar and art space for jazz, soul, and R&B.

3AM: A LATE DINNER DATE

Still Hungry? Peach Farm is serving up last-calls for Peking Ravioli in an unassuming, no-frills setting right now. What are you waiting for?

4AM: WHERE ELSE?

Head to Bova’s Bakery, because where else can you get a calzone, cannoli, and buy your bread for the next day at 4am?

Photo via Bova’s Bakery Facebook

5AM: YOU UP?

Whether an early riser, or late-night lingerer, a walk through the Public Gardens is always a good idea.

6AM: HELLO SUNSHINE

Watch the sun come up at the picturesque Charles River Esplanade, a serene spot to meditate… on what the night might throw your way.

7AM: YOGAAAH

When you treat yourself to a 60-minute vinyasa session at the serene Yogaworks studio in Back Bay, you’ll come out saying aaaaahh.

8AM: PHOTO OP

Acorn Street is one of the most photographed places in the entire city. Go for a stroll and reminisce on colonial Boston while snapping a new-age picture.

Acorn Street via @mikehowell.jr

9AM: THAT IS SO SWEET

Make life a little sweeter with dessert for breakfast at the charming Flour Bakery + Cafe. Order the cinnamon cream brioche!

10AM: DEAR CHARLES

Peruse the iconic Charles Street, Boston’s trendiest postcode with boutiques for the latest local fashions and vintage finds. Our favorite? Good + Black Ink.

11AM: SUMMER READING

The Brattle Book Shop is one of the oldest bookstores in the country. Stop in and find a good summer (or any season really) read!

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