Old world large city like London and Paris...then it's New York. Something more modernish, then Seattle. But again, no US city is that Euro...
I never had this discussion w/ my European friends although it's an interesting question to pose. But I do remember my German friend mentioning he thought SF was the most European city when we were visiting there. But like it's been mentioned before, it's so diverse it's hard to say what's European to start with. What would we nominate as the baseline for an 'American' city?
There are almost no cities in the western hemisphere that resemble a European city in any real way. The two that come the closest are Montreal and Montevideo. Just because people walk around and are not total morons does not make a US city European. SF and NYC are multicultural places, sure, but as far as I'm concerned are both quintessentially American. I will say that Boston is the US city that I think is most similar to London, but I can't really say that it's particularly European, or, frankly, particularly like London.
maybe not the big cities, but there are plenty of smaller towns that resemble those in Europe. I was in Annapolis recently and it wouldn't feel out of place in the Irish countryside. Reminded me a lot of places like Killarney or Kilkenny, although its a bit bigger so maybe Cork.
Boston feels quite British, but not particularly like London (where I live). The North I didn't feel SF was terribly European, and NYC is nothing like anywhere I've been in Europe.
I think the bigger questions is: What's the most "American" Euroean city? Oh how the turn tables have been turned.
Vail Colorado (really Vail Village) is a decent contender -- it is modeled after an Austrian Alps ski town. The best part of Vail is that it is so far away from the poors and so expensive to get to, that you can surround yourself with outstanding people! Spoiler If we expand the question to the include all of North America, then I would nominate Quebec City. Spoiler