Where should we base ourselves in Tuscany and Umbria?

Question

Me and hubby are taking parents in early September. Planning for a total of 6 nights in Tuscany and 3 nights in Rome. Here are my questions specifically.

Should we break the Tuscany stay into:

--2 in Florence countryside

--2 in Siena region

--2 nights in Umbria

OR

Should we only have two destinations? We will have a car and we are going to have a driver for 2-3 days during our stay in Tuscany so we could take day trips.

First time for all of us to Italy!!

Answer 1

I live in southern Tuscany and I would suggest two destinations only. The first in Florence countryside that would cover also Siena/San Gimignano and the second one on the Tuscan/Umbrian border that would cover Cortona, Assisi and other sites. A nice spot would be along Trasimeno Lake.

Have a nice vacation!

Answer 2

The 3 x 2 plan would work out okay especially if you've got a car. There's enough to see or do to occupy your time in only two of the locations if you wanted to do that. It depends on your particular interests and what you want to see and do in each of the areas.

A good location in Umbria would be in or around Perugia. Perugia has a lot of interesting things to see - not the least of which are the old 14th century buildings that are now underground. Assisi is easily accessible from Perugia. In the area around Siena, you could spend a day exploring the city and then a day to see San Gimignano/Volterra or the other hill towns in the wine region. Florence can easily occupy your time for a couple of days itself.