>>>La Corte dei Papi is southeast of Cortona by less than 4 miles, and Montepulciano is just 20 miles away.<<<

Miles on twisty roads in the dark (even only 4 miles) can take longer than you would think. In many areas the speed limit is pretty low because of the roads. If you look at the location of the resort, it's under a mile from the Tuscany/Umbria border. I would not pick it as a base if Tuscany was what I wanted to see. I wouldn't pick it as base for Umbria either. If you just want to chill out at the resort, it looks like a nice resort.

If you look at this map, your resort is between Cortona and Lake Trasimeno. It would essentially be on the brown borderline of Umbria/Tuscany between the two.

http://tuscany.italy-trip.org/map-tuscany.html

I don't find the area around Lake Trasimeno very attractive. It's surrounded by a lot of newer businesses and hotels. On the west side of the lake, the land is more marshy looking. On the east side, you have a more hills.

My sister and I stayed at La Corte die Papi two years ago in August and we loved it. The reviews on Trip Advisor speak the truth. Our decision to base ourselves near Cortona was solidified after reading a husband/wife blog, detailing their years of travel to Tuscany. Cortona was a favorite base for them and their reasons why convinced us. On the eastern side, we drove as far as Assisi. Sis had to stop in Deruta to shop at Grazie. On the western side, we made it as far as San Gimignano, which was packed with so many tour buses, we had a very difficult time trying to park our car. It took two hours to find a legal space. We did not find Cortona very busy during our two week visit.

Tuscany is a very large region and many tourists have their favorite base areas. The research drove us nuts. The first time sis and I went we based ourselves near Panzano to explore the Chianti region and Lucca, which we loved. The second time we went we wanted to be closer to Montepulciano but include Perugia. We loved this area equally as much. I would have no problem making Cortona my base again.

During the Chianti trip, we got lost several times at night because there are no lights on the road. We love wine and we were always intoxicated. For Cortona, we had GPS. It wasn't always perfect but what a pleasurable difference. Hope this helps with your planning.

I'm guessing we will pay a pretty penny since we are returning the car to a different location from where we picked it up but at least it's in the same country, so hopefully not daft money.>>

Mark, you really shouldn't pay over the odds for a one-way hire within Italy. of course car hire companies are getting wise to sticking surcharges on for more or less everything [want to pick the car up from our offices? that'll be an extra £20 please] but picking up in Rome and returning to Como should not cost an arm and a leg.

Being about your 25th I guess you fancy to stay in a romantic spot. I suggest you should stay in a real castle (yeah you can find them even in Tuscany) http://www.spaltenna.it right in Chianti. No doubt you are going to have relax with that quiet countryside around and Chianti is just there to be explored along its white quaint streets.

@wesleymarsh:

<<During the Chianti trip, we got lost several times at night>>

<<We love wine and we were always intoxicated>>

One thing follows from another

I never drive drunk. I don't think I've ever been drunk in my life. But I do enjoy the buzz I get after drinking a really fine bottle of wine. There is some wonderful wine in Chianti. How can you not drive and drink it?

Tuscany at night can be pitch black. It really can feel like you're driving and blind. Trying to navigate a map with an interior car light while buzzed presents a challenge I prefer not to repeat. Thank goodness for GPS. In Tuscany at night, it's worth every penny.

There is some wonderful wine in Chianti. How can you not drive and drink it?>>

either stay in a town or at an agriturismo with a restaurant.

or did I misunderstand the Q?

I'd rent a car to get around. Most nice places are usually hard to reach by bus or train. For a stay I can really recommend Castelfalfi. It's a small village embedded within the hills in the center of Tuscany. They have beautiful cottages, farm houses or villas. The food is great and traveling to Florence or Siena by car only takes half an hour. Oh, and the countrside is amazing

If you need any more info, their website is the place to go
www.castelfalfi.co.uk