I want to see each of these cities, and spend time in 3 out of 4 as in stay a few nights. At first I thought 5 nights in Siena, day trips to Montalcino, Montepulciano, Volterra, Chianti, but that seems like a lot of windshield time. I want to balance moving around too much (every two nights is too much), have time to enjoy a locale, and not spend 3 hours a day in the car going city to city. Now I am thinking 3 nights in Siena, taking time to tour Chianti and go to Volterra. Then off to Montalcino for 2 or 3 nights, taking a day trip to Montelpuliciano and Pienza and maybe a day for hiking and enjoying Montalcino. Then the big choice is Orvieto or Assisi for two nights. Are Siena and Montalcino too close geographically to make sense? Can I day trip Orvieto from Montalcino or just on the way to Assisi if we stay in Assisi? We will be coming from Venice and CT. After Tuscany going to Sorrento and Rome with a total 3 1/2 weeks in Italy. Thanks!
Hi Laurel,
Good thinking! Lodging and parking is expensive in Siena(and parking may possibly be far away) and I found driving near Siena a little confusing. So my point, stay in Siena to see Siena, then use a small town as a base for day-tripping.
Recommendation: I was only Siena once, but saddled with a car for our visit, so we stayed at Fonte dei Tufi (Find them at Tuscany.net). It was a lovely, comfortable, and super quiet agriturismi by the Porta de Tufi. (south gate to the city) But, best of all it had free, secure parking right on site-- a huge perk in Siena. Check tripadvisor for reviews and more info.
Montalcino is a completely different experience than Siena, so no worries about the proximity. Pick the hill town you like best.
We had previously been to Siena so last June we picked up our AutoEurope car at the Via Del Gelsimino 11 location in Florence (away from centers and driving fines) and drove to Radda visiting some wineries. We then drove to Montalcino which we really enjoyed and had the patio room at Rick Steves El Giglio (don't drive into the town- park in a lot on the perimeter) The room was lovely and we went to the farmer's market. The town is tiny but we were visiting wineries which was great. If you want some names let me know. The next day we drove to Montelpulciano. (again don't drive into town).It has lots of stores we ducked into as it was really raining. Stayed at Hotel Mueble and had a great view but uncomfortable bed. The following day we returned the car in Chiusi and quickly trained to Orvieto which we loved. We spent two nights at (RS) Magnolia Inn- highly recommended. Orvieto is a perfect size town. We then trained to Rome. Finally Sorrento.