have been to Boston many times and each trip for me has been about something different. The first time I went it was to see a guy that I had a crush on. Of course, in my weird way I wouldn't tell him that was the reason I had come and made up some weird excuse about doing something for school. (I went to school in Nashville.) So that relationship was doomed from the start. However, I DID forge a great relationship with the city itself. I LOVED Beacon Hill and the Common and Public Garden, but more importantly I loved the shopping. So I did a lot of that on the first trip.
On the second trip, it was winter and I got to see it in a whole new light. I think I actually prefer Boston in winter. There's something about being in a big city around Christmastime that puts me in the spirit. After seeing Christmas trees for sale on the sidewalk, people ice skating on the pond, and having hot tea on Newbury Street I was up and ready to move. It was during that trip that I became acquainted with the theatre district and Chinatown.
Since those first two trips I have seen Boston in all seasons. Now that I am living in New England and within two hours of it I have made several trips for various purposes. It never fails to impress me and I always find something new each time I return.
Quick Tips:
Food
There are some great restaurants to be found in Boston. The North End, or Little Italy, has some wonderful Italian places. Like everyone says, get off of Hancock Street and dive down some of the little side streets to the Mom 'n Pop places and you'll find amazing places.
There are also some really good seafood places around the harbor. I've had some of the best shrimp and lobster anywhere in Boston.
Newbury Street is good for "places to see and be seen", although there are some nice little coffee shops and cafes tucked into some neat corners that can also be found.
Chinatown has, well, Asian food of course. Personally, I like the Asian bakeries although to my palate they don't compare to the Italian bakeries.
And then in the Common there are always hot dog stands which can't be beat on a clear sunny day.Best Way To Get Around:
I would not recommend driving in Boston. Actually, despite the "big dig" it's not a difficult city to manuever. It's the parking that's the problem. if you can find parking on a side street or by a meter then good luck to you and congrats. But parking garages are extraordinarily expensive. Expect to pay around a day for parking. That's also what most hotels charge as well, although that usually includes valet parking.
Boston is definitely a walking city. It's very easy to get from point to point by foot and if you're too tired for that then there is the "T", or the metro. it's very easy to get around on and goes everywhere you want to go. A commuter rail service goes to a lot of the outlying places. A lot of people actually park outside the city and then take the T into town which isn't a bad idea.