Originally Posted by YOWkid
So, I'm off to BOS this weekend to visit two friends finishing up at Harvard... Thus four questions come to mind:
a) What is there to do in BOS? What are key things and sights that I should see?
Faneuil Hall and the waterfront are nice to walk around, if you are a history buff - definitely do the freedom trail. If you like museums, JFK museum down south of the city, and Museum of Fine Arts get good reviews. Newbury street for expensive shopping and people watching (maybe not given b)

)... Pubs on Boylston Street.
Harvard Square. Just for the wandering around and listening to street musicians and the general eclectic feel of the place.
If you are into the theatre, there is a "rush" tickets booth just outside the Public Library (Boylston St. stop on Green Line).
Originally Posted by YOWkid
b) What are the recommended restaurants that won't make me wish my next paycheque came sooner?
Bertucci's is okay, but a little pricey. We had a really great experience at a place called the Naked Fish, down by Faneuil Hall (but also definitely doesn't satisfy the paycheque requirement

).
For romantic Italian dinner - there's lots to choose from in Little Italy and the North End. BUT, if you go, you have to find Mike's Pastry, (look for the line spilling out into the street). You will get authentic Boston customer service and incredible pastry desserts. The freedom trail goes through little Italy and makes a nice end to the day...
Originally Posted by YOWkid
c) Any romantic places to go?
Harbour Cruise!!!! Was our first date and we are getting married Aug 13 so never know???

. Would also recommend just being downtown by the water at night - walk along the harbour can be romantic. Prudential Tower gives pretty nice view of the city lights at night but may be bit expensive.
The Esplanade can be a nice green walk along the Charles river and you'll get a nice "across the river" view of the pretty side of MIT (the other side of campus is kinda depressing) but probably don't want to do it at night - despite how pretty it is, it can be dark and a little isolated. For a different view of the city take the Red Line Outbound towards Harvard / Alewife - it crosses the Charles river and you'll get a nice view of the Boston skyline (you can get off at Kendall and go back if you don't have time for Harvard - though it will cost you another subway token)
Just a note on the subway - anything going towards downtown is "Inbound" and anything away "Outbound." The Green line can be confusing but for most of the places you probably would go any branch will work (just be careful of the E line - it branches off a little earlier than the others).
Would love to offer to meet up and show some of our favorite places but unfortunately with us leaving for the wedding Tuesday this weekend is promising to be rather busy

. Enjoy the city and feel free to post any more questions about any specific ideas (or PM).