Good food? Great streets? Great music? Famous historic areas? Go Red Sox I think "good food" is overrated. 8-) It isn't dependent on any city, because in todays world, you can go to any major city and eat almost anything you can think about from squid crackers and sushi to american beef steak, fries, noodle soup, chinese chicken wok... So unless there are really awesome restaurants in a city (to my mind springs Tokyo which has really awesome restaurants), it shouldn't be used to rank the city. The other 3 you mentioned are very good criterias though. Ignorant Post. Do some reasearch. Quincy Market? Every type of food you can find? Boston has the Best clam chowdah out there. Lobster? Seafood, possibly the best in the World? And I forgot another thing, Great culture and Heritage. The Irish heritage of the town, there's just nothing like it. Almost every person in Boston you find is some percent Irish.