I've figured out I need 3-4 days for Rome.

How many days is good for Tuscany - for wondering around, eating good food + wine,
visiting towns with charm and cuteness?

We will be renting a car and driving from Rome to Tuscany.

How far (better how long) is a trip from Rome to say, Siena? How simple is to go from town to town? Do I have to have a reservation for hotels? Would I be able to find accommodation in early September without reservation? What is good "base" city?

Hi-Have your tried www.mappy.com for directions?? They show you a map & also give you the roads to take & how long they take. Chris

Depending on your map, going from town to town can be quite time consuming. Plus, the beauty of it all just makes you want to take your time! I think that in order to determine how many days you'll need in Tuscany you first have to decide which towns you want to see, do you want to focus on the south? We spent 7 days and really could've spent a lifetime. We rented an apartment and made day trips from there (which I highly recommend) and spent afternoons lazing around the pool - it was a life I could get used to very quickly. I would say at least a week is needed if you want to see several towns and really enjoy the countryside. As for reservations in early September, I would think that would be wise... it's still a popular time to travel. JMO

We spent 5 days in Tuscany and needed more time. Rome to Siena is not too far www.viamichelin.com but don't go straight there! SOuthern Tuscany was wonderful: Montepulicano, Pienza, Montalcino (tons of vineyards around Montalcino). We ate at a great restaurant in Buonconvento called Mario's. I'd rec. staying a 4 nights in this area (easy to drive and get around) and then a few more nights NW of Siena near San Gimignano or Lucca.

How do San Ginigiano and Lucca compare?
Is one cute than the other? Which one has more nice restaurants and Tuscan charm?

We spent a week in Lucca last year, rented a villa with a pool in a restored 16th century farm house from TUSCANY NOW located on a working olive grove. It was incredible, a few miles from the walled city with the most beautiful views and most serene surroundings. I wish we had a few more weeks time. The town was very beautiful, the people very friendly, and the restaurants excellent, especially Da Leo which was an excellent taste of local cuisine not spoiled by tourism or commercialism. I would and will go back to Lucca soon.

I found Lucca and San Gimignano to be very different, although I couldn't say one was better or worse. San G is a bit more crowded during the day (from my experience) and it's less level and larger than Lucca. I enjoyed Lucca very much because it was so serene but San G had much more to see and do and is much closer to all the other "hill towns". Plus, the look of the cities is much different.

We visited Rome, Tuscany and Florence this past September, so I can give you some opinions. DONT go without reservations. We stayed in a charming small hotel outside of Castellina in Chianti. Every day, we saw the clerk trying to help people who stopped in withoug reservations. That hotel and most others are fully booked in September. I can give them a good recommendation - Hotel Belvedere in San Leonino. I thought everything about the place was charming. It sits smack in the middle of nothing but vineyards. Good location not too far off the highway, near Siena.
You could spend as many days as you have. Don't miss Assisi, in Umbria, if you have any interest in religious history at all.
The trip from Rome to Siena is easy. I think it was well under 3 hours.

The answer to your question is simple--there are never enough days for Tuscany. You can return over and over again and still have places to see and things to explore. So, just decide how many days of your trip you want to give to that area and then limit your explorations accordingly. We have spent several weeks in Tuscany over the years and kinow that we will have many more there. It is a wonderful corner of the world. Driving from town to town is not difficult except for the tendency to be drawn to each and every white road along the way. To go to Tuscany is to begin a love affair. If you go to this website and then navigate to Italy 2001 and Italy 2003, you will find info, recommendations and pictures from Tuscany from both trips. Hope you enjoy and find it useful. http://www.janeandken.com