Tuscany / Umbria area Base?

Only five days for Tuscany in a five week trip? How many more for Florence which is in Tuscany?
How many days have you allocated for Umbria?
Tuscany is a very large area and Umbria is to the east of it.
Tuscany- all charming towns and villages.
1. Chianti region-
Greve, Panzano, Radda, Castellina, Siena
2. To the South and east a little from Chianti- Montalcino, Pienza, Montepulciano
I have left out Lucca as it is to the west and not convenient for day trips in the rest of this large area of Tuscany.
3. Umbria-
Spello, Montefalco, Bevagna, Assisi, Todi

Thanks Suki, so in which of these towns/villages that you mentioned would you use as a base for staying while visiting the Tuscany area?

We know this will not be the last time we visit Italy, so have allotted 5 full days to exploring Tuscany and a small bit of Umbria. We have 5 full days in Florence

Would choose a base close to the A1 highway. It gives easy access to many towns in Tuscany. One note of caution. You should check driving times on, e.g., viamichelin, not rely on distances. Here’s an example: once, a friend rented a villa and invited us to stay for a week. It appeared to be close to the A1; however, it was at the end of a long, unpaved, deeply rutted, twisty private road . . 20 minutes just to get to a secondary road, then another 20 minutes to get to the A1.
Montefalco, Spello, and Bevagna can all be visted in a single day.

Hi Sheryl,
I would suggest Montepulciano as a base hands down. It's a perfect sized town with lots of amazing restaurants, great shopping, amazing wineries, and there are always events or festivals going on. Montepulciano has easy access to many wonderful towns such as Pienza, Cortona, Siena, Arezzo, Assisi (Umbria), Perugia (Umbria), etc... The list is nearly endless.

If you decide Montepulciano is a fit for your vacation, I would be more than happy to provide restaurant and accommodation suggestions. Just let me know. Have a great trip!

My family and I have been to this region a couple of times and each time has been absolutely outstanding.

In the past we have used Volterra (my favorite), Orvieto (also a favorite), and San Gimignano as home bases. Each town is small, but not too small. They all are great towns to walk around in the evening and explore and have a wide variety of activities and restaurants. In Volterra, we stayed at a place called Albergo Villa Nencini. The place had a pool, parking, and included breakfast. The B&B was right outside of the city gate, but about a 3 minute walk to the town. Overall, a very relaxing place to stay and my family loved the pool. In Orvieto, we stayed at Villa Mercede. It's a monastery and has parking on site. Very quite and nothing really special, but it's steps away from the main square and very quite a night. We also stayed at Hotel Valentino Centro Storico and they also have parking and are in a great location. In San Gimignano, we stayed in Hotel Bel Soggiorno. They don't have parking but public parking was less than a 5 minute walk away from the front door. The rooms all have breathtaking views and so does the restaurant/breakfast room.

I would stay at any of these places again. The two suggestions in Orvieto are a little more basic, while the other two have more charm.

Bevagna=authentic, picturesque plus excellent access to various worthy daytrips.
I am done. The end.