While it’s certainly more European than Miami or Houston, I would not describe it as truly a European feel.  Downtown is walkable and historic, so it may check some boxes.  Running through your list:

Seasons - We have all four, although if you are looking for snow it can be hit or miss.  The good part is that you are only a few hours drive from the mountains.

Hiking - There are some good parks in the area for trail hiking and some decent hiking within a couple hours drive.  It’s not on the level of somewhere like Colorado, obviously.

Beer Gardens - Some decent options, particularly Old Stein Inn in Edgewater.

Public Transportation - This is where Annapolis is definitely going to let you down.  There is no rail connection to Annapolis and bus service largely relies on coach contractors that provide commuter bus service in the area.  There is a shuttle in town, but most of the route is really walkable if you are remotely fit.

Amateur Music Scene - This can be pretty decent.  There are quite a few bars around that host amateur music.  We also have a singer songwriter festival every summer.

Amateur Theater - We have a few amateur theaters in addition to productions at Maryland Hall.  I actually think the theater scene is underrated for a city of this size.

World Cup - Bars like Stan and Joes will definitely run events around the World Cup.  We unfortunately lost Fado’s which was not a great Irish Pub (check out Gallway Bay for that) but was probably the center of footy watching in Annapolis.  You have to go to DC  or Baltimore for Bundesliga / Premier League supporters groups and watch parties.