Siena the first week in August

I doubt the crowds will be that bad the first week of August. Many Senesi will be vacationing at the beach while other Italians will also be at the seaside avoiding the heat inside cities. Cities like Siena will be mostly in the hands of foreign tourists. I don't know what you mean by the first week not being bad. That's the hottest time of the year in Italy. But you are from Miami, so you'll feel like at home, just not as muggy and no hurricanes.

Hmmmm...well the idea of being surrounded by foreign tourists when we finally get to Italy does not sound inviting. Is there another town in Tuscany that would be a good base for daytime exploring, but provide enough to do at night? (by enough I mean good restaurant and bar selections, and pretty streets to wander up and down and people watch...not dancing in a club until 4 am) :) And the idea of hot temperatures without the humidity sounds like absolute perfect weather! :)

Will you have a car for exploring Tuscany? That will be helpful. If you have a car, not depending on public transport, you can choose anyplace as a base, including an Agriturismo (farmhouse) in the Chianti (between Florence and Siena) or anywhere in the region. If you don't have a car, the best base is Florence, because it's Tuscany's transportation hub. Florence will also provide the best nightlife opportunities. Although many Florentines will also be at the seaside the first week of August enjoying their vacation, however there will be hordes of American tourists (and from other countries) roaming the streets any time of the day. Siena is a smaller city, therefore it will be a little quieter than Florence, but will provide enough opportunities for strolling around and restaurants and bars. Smaller towns and villages are quiet at night, of course. If you have a car, but still want to be in a city with more nightlife, like Florence, you need to be aware of the fact that the historical center is closed to non resident traffic (you probably heard of the infamous ZTL, or Zona Traffico Limitato). This is true for Siena as well. Therefore you might have to look for a hotel at the edges of the ZTL, that is close enough to the historical center but not inside of it, where you can't drive to it. For Florence, consider Villa Liberty hotel. The owner is a friend, It's a nice 16th century villa, outside the ZTL with free parking, also close enough to the center that you can either walk or bike to it (they provide bikes for rent). You can use that as a base and it's an easy place to get out of town by car. Unfortunately they have no pool (few hotels in Florence do). In August having a hotel with a pool would be a great thing. Search around then come back and I'll tell you if it's a good location.

We would rent a car to allow us the freedom to explore the countryside at our own pace. I just came across the city of Montepulciano. Would that be better as a base? By better I mean, it's still a big enough city that will have restaurants, bars, places to wander at night, without being completely overrun by tourists...and still convenient to tour the countryside during the day?

I wouldn't give up on Siena as a base, I've stayed in both Florence and Siena many times and I think Siena has more charm. If people aren't T the beach in August, they may be headed for the hills - good news there is that you'll run into Italians on vacation. Are so is a lovely town not far from Florence and Siena. Two summers ago my friends and I rented a car and split eleven days between Siena and Assisi(in Umbria) and day tripped to one or two towns each day. We stayed at Hotel Minerva on Via Garibaldi, with on-site garage parking. We walked into town and only took the car on day trips.

It will be HOT. We stayed at an Agriturismo 5-10 min south of Siena that had a pool. It was so nice relaxing by it during the hottest part of the day and going into the city in the early morning or evening. Check out Il Canto Del Sole. You will LOVE it in the Tuscany region, absolutely AMAZING!!!