Best Italy holiday for wine and culture?

[bri]

Go to Tuscany.
Rent a car.
Visit these cities: Montelcino, Siena, Montepulcino, San Gimiliano, and for sure Firenze. During this trip, you'll have good italian vine, good food (Tuscany is famous with meat, different soups and etc), a lot of history (even more than you want), and a lot of historical buildings (as you'll feel you're living in the middle age). I can bet you'll love this trip.
1 week is enough.
About italian men, you don't need to look for them, they'll find you..:-) So don't worry about this... Just be open, which means that: look them in the eye and smile, and before you understand, they'll be near you...
By the way, good conversation depends on your level of italian. italian people speak english, but average is not very high, and accent is very thick.
Good luck.

[red_bilberry025]

I'm an Italian girl and I'm writing from Umbria. I advice to visit my region Umbria.. some links (so you can see somethings)
http://www.bellaumbria.net/maps-road-map_eng.htm
http://www.english.umbria2000.it/Default.aspx
http://www.umbria.org/eng/default.asp

[crocchetta85]

Florence and other small villages in Tuscany.....I find them perfect for you

[mareeclara]

I loved the Tuscany area.....I wanted to stay in Seinna (which is simply lovely) but ended up staying in the Sienna REGION!!! Long story on that one...and was actually in a place called Montepulciano...its a little hillside village that has great views of the surrounding countryside and is much more peaceful than other places.....THe place is famous for its wine....there are other places like Chianti too....Florence is VERY busy and its nice to get away, buts its very beatiful and trains can take you to places reasonably quickly (or buses as it needs to get to Montepulciano ether from Sienna or Chuisi.

[robot2235]

You may like Piedmont, Tuscany or Veneto, although they're all beautiful place for both living and toursim, I suppose Piedmont meet the most your request. You may like Turin for "cafe culture and conversation": I put all in the same sentence because cafe in Turin were, especially in 1800, very important place for meeting between people who "made Italy" (or even Europe), like Giuseppe Mazzini.

[Lovely World]

Take the car up route 222, the chianti wine route. Stay in little towns like San Gimignano and Greve, go to all the wine tastings you see along the way, as you make your way to Florence.