Tuscany, Umbria, Northern Italy Hill towns

What time of year? What do you enjoy doing? Will you have a rental car? Have you been to Italy before? If so, where?

Your question is a little vague, so I'll tell you my itinerary. We're flying into Pisa and taking train over to Florence. Staying 3 nights close to the train station taking in the museums. Picking up rental car and moving down to San Gimignano to a agritursimo for 4 nights. We'll be visiting Siena, Volterra and San Gim. hill towns, and basically rambling around the countryside. We're dropping the rental car in Orvieto, and spending the night. Next day, we're visiting Rome for 4 nights staying in a B&B outside the city. If this is your first trip to Italy, I'd suggest starting in Venice for 3 nights, moving to Florence area for 3 nights and spending 4 nights in Rome. We've been to Venice 5 or 6 times, so we're bypassing it this trip. We absolutely adore he place.

Sorry I was vague. Will be renting a car in Rome and going from there. Will likely be in May. Have been to Italy perhaps 10-12 times and have visited the major hill towns of San Gimignano, Orvieto Siena, Assisi. Was looking for smaller, perhaps not so touristy places.

richard,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

We're going back next year, and focusing on northern Italy. Have you been to Bergamo? It's supposed to be charming. Also, a Tuscan town on my list for a different trip is Pienza.

Central Italy, (Umbria Region): Todi, Montefalco, Montepulicano. Northern Italy: Verona, Bolzano, Bologna, Ravenna My 2¢.

I second Ellens choices. I love Verona and Bologna and I wouldn't miss Siena and Lucca.

I forgot. Bergamo is wonderful. Stay in the old city...I forget if it is upper or lower at this moment. I think upper!

It may be a little late to get a reservation, but I'd look into staying a week at an agriturismo and using it for your base of operations. An added feature would be that you will get to know the family that runs the agriturismo. Rent a car and travel out from it to a variety of hilltowns. Perhaps the area south of Siena would give you a good base to drive from. In my opinion, that's so much more interesting than jumping from hotel to hotel every few days.

Adding my 2 cents: Spello, Montalcino, Gubbio, Arezzo and Sansepolcro, Anghiari, Todi, Trevi. Central Italy, actually, but I think your subsequent post puts you in this area.

Thanks to all of you for your thoughtful comments/responses. They are indeed SINCERELY appreciated.

Got to agree with Bob. When we did rural Tuscany and Umbria we stayed at awesome agris and day tripped from there. I also have to vote for a visit to Panzano...if only to eat lunch and dinner at Dario's and wine taste at the Accademia. Pull this up on Trip Advisor and do some reading. We had friends who reccomended this ,and they 'were right on the money".