My friend and I will be in Tuscany for a few days at the end of May. We are thinking of visiting Montepulciano, Montalcino, Pienza, Siena, San Gimignano, Chianti Region and maybe Volterra. As this is my first time visiting Italy, I would like to hear some suggestions on hotels that could serve as home base.

We are renting a car and would like to stay in a central location. Please Help!!!

Here's my journal from 2004 in Tuscany. My cousin and I stayed in Montepulciano and loved it! Maybe my notes will help your plans: http://www.luvtotravel.homestead.com/ItalyJrnl04.html

Monica

How long is a "few days"?
You have a pretty geographically spread out goal.
You might stay close to Siena ,but I need a little more information.

We will be there for a total of 4 complete days. Thanks for your help

If 4 nights,split your stay.
Where are you traveling from and to?

We'll be taking a train from Rome to Orvieto, picking up the rental there and heading to Tuscany. After our time in Tuscany we're heading to Venice dropping off the car in Bologna.

aireslibre,
I would make my base in Siena. When I was there a couple of years ago I stayed at a wonderful B&B called Frances Lodge. This B&B is about a 3-5 minute drive from the town center. If you want to stay in the town center, Palazzo Ravizza gets good reviews on tripadvisor.com. Have fun!

I think you'll find 4 days isn't enough time to hit all those places. You'll be exhausted and won't appreciate them as much if you have to rush through.

If you really want to see the Chianti region as well as the Val d'Orcia (area around Montalcino, Montepulciano, etc) you'll probably do best staying in or near Siena.

You can do Montepulciano and Pienza in a day. Montalcino and San Antimo abbey and a vineyard in a day. Siena at least a day. San Gimignano an afternoon, but it takes a while to park and walk into. I'd choose Volterra or San Gimignano but not both. Volterra is further away from the rest of your choices.

In my opinion there's more to see in the Val d'Orcia than the Chianti region. Chianti region is beautiful, but nothing in comparison to the area around Pienza etc.

So, I'd either base in Siena, near it or somewhere closer to Montalcino/Pienza/Montepulciano. They are close to an hour away from Siena.

Pienza and San Quirico are easy bases in southern Tuscany - easy to park and get into and out of the towns. Both are very small. For my upcoming trip to Tuscany, I'll be staying in Montepulciano at Locanda San Francesco. It's inside the city and you can park at the hotel rather than outside the city walls, which is appealing.

I've also heard good things about Palazzo Ravizzi in Siena. One thing to keep in mind though is that Siena is more like a city than the other towns you mention. So that might affect where you'd prefer to stay.

My husband, son and I will be taking a similiar trip in June. Picking up our rental in Orvieto then on to Civita di Bagnoregio for the tiny town charm. Where not sure how much more we can see in one day so should we head to Assisi or try to see Montepulciano, Pienza and MOntepulciano before stopping for the night?

Sorry I ment Montalcino.

I would see Pienza or Montalcino and head for Assisi the next morning. If you enjoy wine, a stop at Brunello's in Montalcino is a must!

These are the options I would consider.:
1.Go from Orvieto to Pienza area and stay there two nights.
Drive to Chianti and stay there.
Drive to Bologna.
Do not see Siena.

2. Drive from Orvieto to Siena area and stay there.
See Siena during one of the evenings.
See what you can and drive to Bologna.

Since you are driving north either works. All will get is a taste ,but it'll be enough to tug you into returning.