Just found out I am heading to Boston, the bad news it for work, the good news I have per diem. It looks like I will have some time in the evenings to take in the city. I might also have a full day on the back end. I will be staying right next to the TD Garden. I was looking for some great food, good drinks, nice coffee, fun things. And if I do have a day, what is the perfect way to spend a day in Boston. I wont have a car but can do a lyft or ride the train.
Faneuil Hall is a great area and you can grab food for lunch or dinner. A Great way to see sites and get to know a city is to use Stray Boots. While visiting family last summer we did one in Boston. I have also done it in Philadelphia, I live outside Philly and found it a great way to see and learn things I wouldn't have. In Boston we did the Northend area. You can do it by yourself or with others. You walk the area and answer questions, like a scavenger hunt.
You're lucky because you don't need a car to get around Boston. Walking will do! So you live in the North End with is Boston's "Little Italy" and if you like italian food Hanover St and Salem St are full of restaurants. The Freedom Trail is easy to follow, as it's marked down on the street. Start from Old North Church (or wherever you find the trail on Causeway street and follow it up to Massachusetts State House opposite Boston Common.
The Back Bay and especially Commonwealth Ave is nice for a walk if weather permits. a couple of places I do like in the Back Bay is Papa Razzi (yes I do love italian food) and Max Brenner which is a chocolate place/restaurant.
For further "sightseeing" you can take the red line from Downtown Crossing or Park Street Station and head to Harvard Square. You can walk a bit around Harvard Yard and definitely find many restaurants like Alden & Harlow for dinner.
I have sort of compiled "a day in Boston" in my blog here: http://aspectsofstyle.com/2015/01/07/architecture-chocolate-and-lobster-roll/
And here are also my "presentations" about Beacon Hill and Back Bay
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If you're staying near TD Graden your best bet to see Boston is the North End and Faneuil Hall areas. The North End is touristy but still fun while faneuil hall has several good bars and clubs. Coffee shops abound, just pick one that looks crowded.
After reading Anna's response most everything I was going to state has already been mentioned. I agree with everything she has. I do think Harvard Yard is interesting but in my opinion is overblown as a destination. I think Harvard Squareis a must if you have an evening. It is eclectic, bustling and has tons of places to eat. Stay away from the larger type places that attract tourists like John Harvard's. Check in with something unique like Clover or Felipe's Taqueria. These are inexpensive and very casual places but very good food. I personally love Clover's Egg & eggplant sandwich. Sounds unusual like Peanut butter and banana but it's the best $6 you'll ever spend. I recommend not eating at the restaurants Faneuil Hall. It is way too touristy. The Quincy Market section of it is nice though. You get a lot of diversity. If you've ever been to Reading Market in Philly it is along those lines.
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