Photo: Katie Haugland

Morning

Chances are you need some coffee. I may be excommunicated from Boston forever for suggesting this, but skip Dunkin’ Donuts. Hit up an indy coffeehouse instead. Where to? Boston’s public transport is so great that it only needs to be defined by one letter. Locals call it the T. Hop aboard the Red Line and head over to Boston’s Left Bank, the super hip and ‘wicked smaht’ Cambridge. The intellectuals at Harvard and MIT love their coffee, so check out 1369 Coffehouse. Or, if you love to hate yourself for wanting overly complicated baked goods and perfect cappuchino served up by hipsters who hate you, hit up one of Darwin’s several locations.

Now that you’re properly caffeinated, check out the views. This is where Boston’s excellent bike share program comes in. Grab a Hub Bike and feel like a local cycling along the Charles River. The Mass Ave Bridge
has great pedestrian access and offers a kickass view of the entire city. Hang a right and cycle all the way to fabled Fenway Park, or hang a left and cycle along the emerald green Esplanade all the way to the super historic Beacon Hill. Bonus, you’ll be right by the Swan Boats in the Public Garden if you’d like to take a load off and go on a little paddle.

Midday

If you headed toward Beacon Hill you’re in luck. There are two awesome options for lunch. Walk over to Chinatown for some authentic dim sum at China Pearl, or hit up the North End for some seriously awesome Italian grub. Don’t forget a cannoli at The Modern or Mike’s Pastry!

Afternoon

Let’s be real. You’re going to need a disco nap.

If you don’t, or if you headed up to Fenway this morning, check out the Isabella Stuart Gardner Museum. ISG was an eccentric Boston millionairess, who had an Italian villa brought over from Europe and reassembled brick by brick in the Fenway where she filled it with priceless art, nicknacks and her written correspondence with some of the most celebrated artists and writers of her era. She willed it to remain untouched after she died so everything is exactly as it was at the time of her death, including the empty frames where a couple of stolen Rembrandt paintings once hung.

Evening

Are you feeling classy or trashy?

If class is your bag, head to the Beehive in Boston’s South end where you’ll be smitten with their eclectic cocktail and food menu. Feeling theatrical? The BCA is right next door and offers up some of Boston’s most cutting edge theater. Then head on over to Wally’s, a hole in the wall that’s Boston’s oldest Jazz cafe, where there’s live music every night.

Trashy? Head back to Cambridge, kid. If you love live music and that rock n’ roll vibe, no trip to Boston is complete without a trip to the Middle East Restaurant and Night Club. Three stages across 2 floors attracting the best local and international acts 365 days a year. Plus, they run a really decent Middle Eastern Restaurant where you can get your grub on between gigs. Need to dance off all that falafel? Stop by next door at Zuzu.

10 more wicked fun ideas:

  • Head to the waterfront and check out the ICA, where it’s anybody’s guess what’s more breathtaking, the art or the waterfront views.
  • Snap a selfie of yourself glowing in the dark at the Lawn on D.
  • Take the Water Taxi from the World Trade Center across the harbor to East Boston where you can nosh on Australian food at KO Pies.
  • Throw together a picnic lunch and head to the Boston Harbor Islands.
  • Catch a flick or live show at the charmingly retro and beautifully preserved 100+ year old vaudeville movie house, The Somerville Theater.
  • Grab an ice cream at JP Licks and hang out with the street musicians in Davis Square.
  • Hop on the Orange Line and head over to the Arnold Arboretum in Jamaica Plain. The arboretum is chock full of gorgeous species of flowers and trees, and boasts kickass views of Boston.
  • Be a kid again at Grownup Nights at the Boston Children’s Museum.
  • Go sailing or Kayaking on the Charles.
  • Take the ferry across Massachusetts Bay to Provincetown and check out the galleries, restaurants, and vibrant gay nightlife.

Get Around:

  • Take the T like a local.
  • Hop on a Hub Bike.
  • Strap on your sneakers. Boston is a great walking town.
  • If your feet get tired, everything’s close enough that Uber rides probably won’t break your bank. This may be your best option after midnight, as the T shuts down around 12:30.
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