We will be staying at Giglio in Montalcino for four nights. We will be traveling up from Rome. We will be renting a car, but aren't sure where we should rent it from. Do you suggest we rent our car in Rome and drive up? If so, will it be relatively easy to drive there?
Our next stop, after we leave Montalcino, we will heading up to stay in Florance for 2 nights 3 days. Any suggestion which towns we should visit from Florence? Any suggestions would be great! Thanks!

KDP,

On my last trip I left Rome via train to Chiusi. Picked up car and drove to Montalcino. If you do this, you will pass through (driving) Montepulciano and Pienza on the way to Montalcino.
It was very easy.

From Montalcino (3 night stay at Il Giglio) I visited on day trips:

Montepulciano
Pienza
Sant'Antimo
Monte Oliveto

from there drove on to Cortona and Gubbio, Assisi, Spello

I'm enjoying some Rosso di Montalcino as I type!

PS - Be certain to have dinner at Grappolo Blu. They open at 7pm and say Ciao to Luciano and Mariapia. Drink LOTS of Brunello (heaven).

Have a wonderful trip. We recently came back from a very similar trip ourselves and I am pasting my trip report below so you can read it. Let me know if I can help with anything else specific.

http://www.fodors.com/forums/threads...p;tid=34884020

KDP,
Another possibility is to train to Orvieto, tour the town then rent a car there. The drive up SS2 is easy about an hour and a half.
I have spent a lot of time in Montalcino and would be happy to answer questions or offer day trip advice. Feel free to e-mail.
Henry

If you're planning to use a car while in Florence, may I strongly suggest NOT! We've been totally comfortable driving all over Italy - the Amalfi Coast road, even in Rome - but Florence took it to another level. One way streets, pedestrians only, do not enter. And if a map has been drawn to show you how to do it, we didn't have it! The only town I'd visit once in Florence is Fiesole to view Florence at sunset, and that can be easily done by city bus.