Tuscany & Umbria - Planning

Are you spending time in Florence in addition to these plans?
I would definitely go with Option 1 - but perhaps include 2 nights in Siena itself to get a feel for the city at night.
Lucca area (5 nights), Siena (2 nights), Pienza area (5 nights), Montefalco area (5 nights)

We will visit Florence and Siena, but we will not be staying there. We made the decision to stay in the countryside for all nights.

Many years ago (1997?), we rented a cottage very close to Chiusi. From there, we were able to take day-trips to Perugia, Montefalco, Bevagna, Assisi, Spello, Gubbio, Orvieto, Arezzo, Cortona, Montepulciano, Montalcino, and Pienza. In short, it was a terrific location. If you put yourself in that area, with easy access to the A1, you'll be able to see all those towns. A second base, near Lucca (?) would give you access to places further north. There is much to say in favor of reducing the number of moves. Maybe a modification of #1 would work, with eliminating a move to Montefalco, adding a day or two to your northern base, and adding the rest to your southern base. Just be careful in choosing your locations. Accommodations that may appear to be close to major traffic arteries, may in fact not be, in terms of time. Here's an example. A friend rented a villa near Sarteano. and invited us to join her. What she didn't realize was that the trip to Sarteano, on a 2-lane, hilly, curvy road, took 20 minutes. That after a 20 minute drive on an unpaved, very bumpy private road! Those 40 minute treks twice each day were not only time-consuming, but very exhausting for the driver.

Rosalyn, I agree that location is very important.

So i have made a little progress...

Booked 6 nights at a B&B steps outside of Greve in Chianti.... This will be the first leg.

Still working on the remainder.

I think that three locations isn't too many. Especially if you're making day trips in the area, after a while you might get tired of a lot of coming and going from/to the same location. So I would vote for three destinations.

Now, which three is the difficult part. I've been to / stayed at all three areas, and liked them all. Are you very much into wine? If so, then I would definitely include time in the Montalcino / Montepulciano area, for the Brunellos (a little south of Pienza). Or, if you really like Chianti wine, then the B&B that you've already booked will be great.

Siena area, if you are staying in a village/town west of Siena, then I guess I would choose option 3. Then you could visit Certaldo, San Gimignano, Volterra, and of course spend time in Siena.

But you've chosen the Chianti area, so I'm not sure if you're even still considering option 3.

Such lovely decisions to be able to make - makes me want to return to the area.

Lexma,

Yes sorry for the confusion. We chose option 3, with a little change to the first part.

Our itinerary now stands at:

A. Tuscany/Chianti area (6 nights): Sept 7-13 The Chianti Classico wine festival is Sept 10-13 in Greve So excited. Will be staying at B&B Casale Le Masse steps outside of Greve in Chianti.

B. Tuscany/Val d'Orcia area (6 nights): Sept 13-19, looking at B&B La Casa di Adelina in Monticchiello.

C. Umbria/Montefalco area (6 nights): Sept 19-25, looking at B&B Villa Mustafa.

A. Tuscany/Chianti area (6 nights): Sept 7-13
Of the 3 locations (A,B, C) this one is the one that is best located to visit most famous towns and cities: Florence, Chianti, San Gimignano, Volterra, Monteriggioni, Certaldo, Colle Val D'Elsa. This is actually the closest of the 3 if you want to visit Pisa and Lucca. Siena is equidistant (in terms of time) from A and B, but in miles A is closer as well.

Therefore you should probably allocate the most nights to this location A.

B. Tuscany/Val d'Orcia area (6 nights): Sept 13-19.
This area is good for the Val D'Orcia, the province of Arezzo (Arezzo, Cortona), Castiglion del Lago in Umbria, and even all the way to Orvieto. Even Perugia is close by. Siena is probably closer from Greve (location A). This area deserves your second highest allocations.

C. Umbria/Montefalco area (6 nights): Sept 19-25
This area is good for most of Umbria, but probably 6 nights are excessive. All you have left to visit is Assisi, Gubbio, Spello, Spoleto, Todi, and possibly Perugia, unless you visit from the Val D'Orcia. It doesn't take long to visit those towns, they are really small.

I would divide the nights something like this, give or take, depending on what you want to visit and for how long:
A: 7, B: 6, C: 5
If you want to see Florence for 2 days and Siena for 1 from Greve you might want to allocate even more to Greve.

Of the 3 locations Greve is closer to the most important large cities and famous sights.

Roberto,

This is excellent information and so well thought out. I will take what you propose under consideration and report back. Thank you.