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
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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