Here is what I am planning: Florence 2 days Siena 1 day San Gimigiano 1 day Hill towns 1 day (Montepulciano, et al)
Chianti wine tour 1 day The question is would it be better to stay all in one place or spend two nights in Florence then rent a car from there and spend the rest of the nights elsewhere? Also, in what order would you do those things? We will be coming from Rome. thanks for any help!
We prefer to stay in Florence, then drive around.
Pick maybe two more places to stay and drive to visit the other places from your two home bases. You can make a circle each day and never go on same road twice. Enjoy.
FWIW, we did 6 nights in Tuscany last fall, 3 in Siena and 3 in Montalcino, which allowed us to see a lot, but not Florence. I liked experiencing 2 very different hilltowns. If Florence is important to you, and you still want to experience hilltowns you could stay in Florence for 4 and one other town for 2, minimizing your time spent changing locations. From Florence you can daytrip to Siena and San Gimignano, and do your Chianti tour if you like. Or you could stay in Siena 4 nights and daytrip to Florence, and still do San Gim & the Chianti tour. You can then stay in Montalcino or Montepulciano and take the beautiful drive between those two towns.
Two friends and I spent 6 days in Siena as our home base, and drove to all the places you mention. Florence would work just as well. The cost for gas for day trips was far less than I expected.
Lisa: Please report on your trip when you get back as your itinerary sounds much like what I would like to do.
Thanks.
Lisa: My wife, daughter and I spent 7 days in Florence last month as part of a 2-week Italy trip. We broke up the Florence stay by making days trips and loved it. There is a car rental (Avis) office not far (walkable) from the city center but be advised that they close at 6PM so you might be better off renting for a couple of consecutive days. We spent our first full day in FLorence at the Academia and the Ufizi and the next day we hit the road to Sienna and San Gimingnano, picking up the car at 8:30 and getting back before 6. The next 2 days were spent in Florence (Pitti Palace, Boboli Gardens, Galaleo Museum, Duomo, etc) and then another day on the road, visiting Montepulciano and Cortona. It worked out well for us because we had rented an apartment for our week in Florence so we had a nice, money-saving base. Have a great time.