11 day Tuscany tour - need help with planning

All roads (and trains) lead to Rome. And yes, avoid driving inside historical city centers or you will likely be sent a very large fine.

Of the few places I've been in Tuscany and Umbria, Assisi is my favorite. Siena is also worthy of a visit.

I love your plan of three trips!

It might be better to count nights rather than days, since days can be partial or taken up nearly completely with travel. Will you have 11 nights on the ground?

A couple of years ago, two friends and I spent 11 nights split between Siena and Assisi and took daytrips from these cities by car. Some of the towns we visited from Siena were Monteriggione, Volterra, San Gimignano, Anghiari, Sansepolcro, Arezzo, Montepulciano, Montalcino, Greve in Chianti. We all had been to Florence before so we skipped that, but you may want to spend two or 3 nights there and stay at an agriturismo for several nights to make getting to the hill towns easier by car (no ZTLs). From Assisi, we visited Gubbio, Deruta, Spello, Bevagna, Todi, and Trevi, with a couple of other stops along the way for lunch and a quick look around. Basically, if there was something at the top of a hill, we drove toward it.

The hotels we chose had parking onsite (Siena, covered garage parking for a few euro per day) or nearby (Assisi, parking was at the foot of the Rocca Maggiore with a bit of a walk down).

My first trip (of 3) to Italy was also to Tuscany, spending 1 week in one place and doing day trips from there. I was actually on a small group tour from my local art museum and the tour was called "the art and architecture of Tuscany". Of course since it was a tour we traveled by bus but in your position I would definitely rent a car even if you don't use it when you go to Florence (and maybe Sienna), you'll want it for the smaller towns and the countryside. We stayed in Montecatini Terme which is between Florence and Lucca. On day trips we were able to see: Florence, Pisa, Lucca, Sienna, Pistoia, Prato, Cortona, Arezzo, San Gimignano, and Volterra in addition to a couple of countryside villas and a trattoria in a vineyard up in the hills, for a multi-course dinner with wines.

In your place, I would probably stay in Florence for a couple of nights since you're flying into there, and then rent a car and stay in a smaller city or town in the countryside for the rest of the time, maybe even at an agritourismo, and venture out by car from there.

On the Umbrian side, I would add, along with the suggestions above, Castiglione del Largo and Cetona.

Last May we did 12 days in Liguria and Tuscany, and we had been to the latter at on at least 4 previous trips. I doubt that you'll get tired of it. Zoe and the next poster list many of the attractive towns. I'll just add Pitigliano, a little less well-known, but interesting and attractive, and close to some other towns worth visiting, like Sorano, Sovana, and Saturnia. You might want to consider two bases, one near Florence and another south of Siena, to cut down on driving.

hal,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

You might want to look for small villas using www.tuscanynow.com or www.villasofdistinction.com. We are staying in a villa just south of Siena this summer. The past two summers we stayed in villas near Lucca. I've used both of these companies with good success.

From the Siena area you'll easily be able to drive to many small villages and soak up the atmosphere. Get a good guide book to help you determine which small towns you want to visit. You can use googlemaps to see where they are in relation to one another and get directions and drive times between them.

Donna

I have been to this area many times and enjoy just driving around with a picnic lunch and stopping in whatever village looks interesting.... no particular plan. Of course, I have a general idea of the villages I want to see, or vineyards I would like to visit, but always ready to simply follow the road. As far as going to Florence, it is certainly easier to take a bus/train into the city and leave your car. I have found parking in Florence but it can be a problem. I prefer staying in a village and visiting Florence as a day trip. I stayed there last year for 4 days and while it was enjoyable I prefer to awaken in a quiet village. I stayed in a wonderful little hotel in the tiny village of San Donato. Nothing much there except a winery, a few buildings and a beautiful vineyard. Little B&B was called Antica Dimora... shutters that opened to the hills of Tuscany... it was amazing.

Wow, so many good responses, thank you all for the input and please keep it coming. To clarify, I will have 11 days and 10 nights in country. I was hoping to stay outside the metropolitan area in a village for rural area, simply for the relaxation concept.

Obligatory disclaimer: everyone's travel preferences are different. Personally, I would stay in Florence for a night or two at either end of your trip. The travel in to the city by car can be stressful, easier by bus or train, but the city is really crowded during the day and very charming at night, so it's nice to have some time there when the busloads of tourists have departed. My last trip, I spent a week in Vico D'Elsa and a week near Passignano sul Trasimeno. From the Val D'Elso we visited Siena, Florence, Greve in Chianti, San Gimignano, and many markets. From the lake, we visited Montalpulciano (our lunch at the Osteria Dell'Aquachetta was the highlight of the trip), Assisi (fantastic) and Cortona (overrated). I found driving very easy during the day, but wasn't so keen on after dark, so we had fabulous leisurely lunches out and more simple picnics or cooked at home most nights. If you are staying in a rural place for a week, there may be relatively few restaurants near by. Have a fantastic time.