Best Location to Stay in Tuscany

It's as good as most any in the area. You might add Montalcino and Montepulciano on the list as well. Note that Cortona will take a bit to get to but once there, don't miss Perugia and Assisi. The point here is that most any place in that part of Tuscany is just great. There's a lot to see.

Know that to see Cortona requires either driving around Siena and then over or taking a bit of a windy road over the mountains through Montevarchi. Not a big deal, but plan for a bit of driving.

We are spending seven days in Tuscany... a train from Cinque Terra and then picking up a car in Pisa. We are staying at a winery near
Siena. We have been researching day trips and found through one of the wonderful people on this site...this site for road trips... slowtrav.com/italy/monte_cetona.htm We are staying at a winery near Siena, we are basing our day trips from there. We are going in May.. and will be happy to share our experienes if you want.

Have you considered the Casentino Valley? It is a hidden secret that is a 45 minute drive to Cortona, Arezzo, and other fabulous hill towns. There are not a lot of tourists, but we so enjoyed seeing the Castel at Poppi, Castel of San Niccolo, and had great food in every town. Another great town nearby is Anghiari, which is noted for the Bussati family and their beautiful linens, and the original factory where they are made. Such hidden secrets. We stay in a villa close to all these sights, called Dei Mori La Massa. It is also a hidden secret, and run by the owners of Dei Mori Bed and Breakfast in Florence. (A Rick Steves pick in his guidebook)
Would highly recommend to you.

Just like Cortona, Arezzo would take some work to get to (or drive there after you've visited Cortona) but it's a lovely Italian city. If you want to go there Oct. 1 or 2, you'll be in Arezzo when they have their monthly antique festival going on, everything out in the streets in the center. (My great grandmother's brother started it, so it holds a bit more significance to me, but it's cool to see!)

Diana, It sounds like you are doing what we are planning. CT to Lucca on the train, then bus to Pisa that stops right in front of the tower. We are renting a car there. Have you rented yours yet? Who did you end up going through? I will be excited to follow your trip and experiences.
We fly into Venice, 2 days; then take the train to Florence, 3 days; train to Cinque Terre for 2 days; and then on to Tuscany, Orvieto and Rome and head home from there. We will be gone 24 days to celebrate our 50th wedding anniversary. Your blog is a fantastic idea!

Gail, I did something very similar to you. We went from CT to Pisa, checked our bags and saw the tower, then came back and took a cab to the airport to rent a car. THEN we drove to Lucca, then on to San Gimignano near our farmhouse. This worked out very well for us. I did find that it was a practical location though I also decided that if I were to ever do it again I would rather be a bit more central (closer to Siena) as it would have made more places a shorter drive. We went everywhere on your list except for cortona which we decided was a bit too far away. volterra is not to be missed and not a far drive. When you go to Siena, try to find the San Galgano ruin, spectacular! Also Monteriggioni is close by and worth a stop. Same can be said for Certaldo and Colle di val d'Elsa (especially if you like crystal :)). huge congrats on your anniversary and have a fantastic time. I found Italy in October to be wonderful - especially in Tuscany. The weather was certainly bearable, and it was nice and quiet. We had the entire agriturismo property to ourselves!

Debra, we are staying at a farm stay as well in San Gimignano. It is at Poggiacolle. Is that by chance where you stayed?

Gail, we stayed at Podere Poggio ai Cieli (http://www.poggioaicieli.it/index.html) - very budget-friendly type of place but warm and comfy and fine for two 20-something friends. Looking at the maps, they are pretty close to each other, I would say your location is a bit more central/convenient in my opinion. It's so close, you may find yourself going into San Gim for dinner in the evenings after your sight-seeing. we did that once or twice and it was lovely!

Thank you so much everyone! I appreciate the input.