Town for 2 nights in the country?

Orvieto is my recommendation. Try B&B Ripa Medici, small. quaint, quiet. Good local restaurants, not too expensive, and hiking the Rupe is worthwhile, in addition to seeing the Duomo. Perfect spot for 1 1/2 days or so.

Will you be driving?

Well I'd hoped we could rent a car from La Spezia and drive, but all of the websites are saying nothing is available - maybe because it is last minute (we are looking for the nights of August 6 & 7, to return the car on the 8)? We have our destination narrowed down to either Orvieto or Montepulciano - there are some bed and breakfasts that look great with availability, but now I'm worried about how we will get there. We will have been in the CT for 2 nights so will be coming from up there - any advice on where to find a car (I never knew renting a car was so exclusive, or maybe I'm missing something on the website) or another way to reach the area?

After leaving the CT we took the train to Lucca, a charming town, and picked up our car there. That way you can drive to your next town through some beautiful countryside. Check out your option of drop off places before booking your place to stay.

Without a car, you can visit Cortona, an amazing hillside town just south of Florence. My wife & I just got back. RS tells about it in his guides. Casa Betania is a a great value, but simple. No Tv, but WiFi for 5 Euro a day. Be ready to walk up & down a lot of hills, though. that's what makes it a hill town.

Try www.gemut.com for a car. They beat the price of other sources online for me last year. Send in a request for quote then have a nice chat with Andy to seal the deal. Worth a try. FWIW dropping a car in Orvieto is easy. Train and funicular are right by the Hertz drop off.

Amy, some rental car companies will only book for a minimum of three days. That's probably why you can't get a quote. I just checked AutoEurope online and you can get a car in La Spezia and drop off in Orvieto at the train station. An economy car is about $180 for the three days. You can also check with Kemwel online. If you are renting a car you will need to get an International Driver's License at your local AAA office. It does not require a test. It costs $15 and two passport size photos which they can take there if you don't have them with you.

Amy, while I have not been to either town, I do know that Tuscany has always been our favorite area and I was about to suggest you stay in Pienza at the lovely B&B in which we spent 2 short days - then realized you didn't have a car. So in that case I'd still recommend Montepulciano - we did drive through that while touring out of Pienza and it looked lovely, has great wine, and is in Tuscany. So that would be my vote. And if you are still looking for a car I second the rec to check AutoEurope. I use them for all my rentals - they are a consolidator to the bigger firms so maybe they have some access to other cars. Good luck!

Thank you all for the suggestions - I tried gemut for a car but never received a response for the quotation. Also, when I went directly to the website of the major car rental companies (Hertz, Avis, etc.) it brings up options for rental for the short time period - but all they have left are manuals which unfortunately doesn't work. So we have decided to stick with train transportation and hope for no strike. As between Orvieto and Montepulciano, do yall have any advice? From what I can tell, Montepulciano seems much smaller, which is what we were looking for (but also harder to travel to without a car)? On the other hand, I've read Orvieto recommended over Montepulciano - but then I worry about it being overcrowded with day visitors from Rome. I am trying to plan this while simultaneously studying for the bar exam, so it's very difficult to research as much as I would like to. Any suggestions on travel to these towns along with which you prefer is appreciated!

Montepulciano is great but (as you surmised) difficult to reach without a car. The train station is 5 miles from town and only served by milk-run trains. Then you must take a bus into town (eight a day; none on Sundays). You can get to Montepulciano by bus from Chiusi, which is on the main Florence-Rome train line. Either way, I'd suggest taking along the taxi phone number: 335-617-7126. Since you mentioned Umbria, you might look into Spello. It's half the size of Montepulciano and is on the Perugia-Assisi-Foligno train line. I've been to Orvieto and Montepulciano and enjoyed them both, but Spello's next on my list!

Orvieto is amazing. The only area that gets crowded with tourists is the area in front of the duomo. The views down into the valley from this hilltop town are gorgeous. And it's famous for its white wine - Orvieto Classico. We stayed at the B&B Garibaldi and highly recommend it, especially the Yellow Room. Check out my Orvieto pics from this May here: Orvieto pics