Hello Shane!
I can recommend Portugal- Lisbon, Spain-Asturias and Italy-Rome.
Lisbon is a great city with a lot of history and to be there is it like travel back in time. Tiny streets, small cafes on every corner, people hanging out the window
If you go there, you should stay in a city center, in old neighborhood like Alfama or Mouraria and rent a small apartment.
Asturias- very recommendable if you like an active holiday and nature. It is beautiful there: mountains, lakes and rivers, fresh air and you can do all kind of activities.
Rome!!!! Wonderful city, many things to see!!! Delicious and relatively cheap food!!! You can find a small hotel in a city center and cheap (for Rome standards, around 100 EUR per night).
Hope it can help you somehow