Boston will always have a piece of my heart. I spent my freshman year of college at Boston University and have been back to visit several times since. If you can swing it, go on Marathon Monday – it’s unlike any other sporting event or celebration I’ve ever been to. It really is the BEST. On Marathon Monday I would recommend starting in Kenmore Square and walking towards Brookline. Cover as much of the race route as you can -it’s a super festive atmosphere and all the bars along the course are packed!
City Guide below –
Freedom Trail. So. Much. History. And, if you take the ferry back from Charlestown the views of the city are amazeballs.
Duck Tour. Cute, quirky way to see different parts of the city.
More Faves (by neighborhood):
Beacon Hill/Back Bay:
Beacon Hill Pub – the divest of dive bars. We went during the afternoon and there weren’t a ton of people around but you could imagine that it’s a hot spot on Friday nights.
Explore the shops in Beacon Hill – start on Charles St.
Flour – cute Boston area chain with great breakfast, lunch and coconut macaroons.
Mike’s Pastry – go to both Mike’s and Modern and then cast your vote for best cannoli!
Myers + Chang (one of the owners is on this season of Top Chef!)
The Butcher Shop – amazing cuts of meat, great sides and awesome neighborhood atmosphere. If I lived in Boston, I definitely try to make the South End my home. All the charming restaurants and row houses are fun to walk past.
L Street Tavern (the bar made famous in Good Will Hunting)
Shamrock Pub – doesn’t look like much from the outside, but seems like it was (and still is) a watering hole for local union workers. An interesting spot that you wouldn’t find in a lot of other places.
Eagle’s Deli (take the T to Cleveland Circle)
Pinocchio’s (near Harvard Square)
Michael’s Deli (in Brookline)
Hope you enjoy!