Hi, we want to make a 3 stop loop of Tuscany. 2 stops will include Siena and CT. What would be a good 3rd stop? Should we fly into Milan or Rome? We will be renting a car. Is that easier in Milan or Rome? Thanks!
Maureen - If you want to venture further south into Tuscany, the Montepulciano/Pienza area is nice. It's about 2 hours south of Siena. If you want to stay in northern Tuscany, consider Lucca for your 3rd stop. Pisa would be your best bet for an airport, as it's in the heart of your itinerary and renting a car there will probably be less expensive. If you want to focus on Rome or Milan airports, Rome would be the logistically better choice for a Tuscany trip, but Milan airfares are often much lower and that could make it the better choice. Open jaws - into Rome and out of Milan, or vice versa - is another option to consider if you decide on CT, Siena and southern Tuscany. That would minimize back tracking. Sounds like you're planning a great vacation. Enjoy!
Maureen,
If youe schedule allows being in Montalcino at the end of October see http://www.montalcino-tuscany.it/sagra_del_tordo.htm
My third stop would be Orvieto. Rather than sitting on a hill it sits atop cliffs. You can tour underground tunnels dating to the Etruscans. It has a major Cathedral built after the Corpus Christi miracle there. We picked it because it was in Umbria close to Rome. Overall it was the nicest surprise of our trip.
I would also make a brief obligatory stop in Piza (maybe two hours including parking and walking to the leaning tower). I would skip Lucca, it has a neat 17th or 18th century wall but overall far from the best stop. I would also add San Gimignano as a day stop (maybe three or four hours of walking). Even though it's a tourist trap, it's a great medieval period town and the prices are no higher than elsewhere in Italy.
We liked Siena too.
Be sure to get a GPS system in your rental car and don't leave until it speaks English. Maps are next to useless; street names and addresses are rarely posted in Italy. The GPS will save you hours of driving.
You can fly into one and out the other, that way you won't have to back track. Also, I wouldn't skip Lucca. I think all the towns in Italy are interesting, just some a bit more than others, personal choice. Get some good books and read up so you will sure to visit the cites that interest you the most.