I want to move from Hawaii to Florence or Tuscany

I am an International Sales Manager for luxury hotels/resorts here in the US. I have been in Hawaii for too long and don't like the heat or beach scene anymore and have always wanted to work and live in Italy. I am also 45 and single so it would be nice to live in an area that has great hotels/resorts, but is also not such a big city, that I would not be able to meet or date men my age too. I have only been to Venice, so I am not familiar with other areas. I also do glass art, and know that Siena and Florence seemed nice, but again is this too isolated or too countryside for me? Any advice would be appreciate. I would be more than happy to return the favor on advise to the US (I have lived in most major cities). Aloha Leilani