My girlfriend and I will most of April visiting the northern half of Italy. Many Thank You's to the various people here who've shared their knowledge so graciously.
Our plan is to spend our first 12-14 days in Venice, Florence, the CT and Lucca. After that we'll rent a car and explore towns in Tuscany and Umbria. The ones I have in mind after reading the forum are Sienna, Montepulciano, San Gimignano, Volterra and Monticiano, followed by Perugia, Assisi and Orvieto. (We'll return car in Orvieto, and take a train into Rome for flight to Madrid and next chapter...)
I'd like to base out of 1-2 locations and do day trips, so we minimize "one-night" stands. At the same time, I'm sure some of these towns are especially enjoyable in the evenings and mornings, when locals outnumber the tourists.
So..which 2-3 towns would make your "stay over" list, and why?
Also, can you suggest any places that offer particularly good hiking or biking options? I know the region is hilly. Looking for hiking trails to great overlooks, or places to ride with minimal traffic.
Thanks again!