Two weeks+ in Tuscany.

Well it just depends on what you want to see and do, as well as how much driving you like to do. I would tend toward two bases--one for Florence and one in a more rural area.

For me, it is easier to spend the time in one place and drive the Tuscany countryside from there. There is nowhere in Tuscany that can't be reached in a couple of hours driving time from one place. Easy day trips. Umbria too

I guess it depends on how much driving you want to do.
You could always do Pisa and Lucca from Florence by bus or train and the rest from somewhere just south of Siena, around Buonconvento for instance.
This is part of the Crete senesi and considered by many(me included) the most Tuscan region of Tuscany and perhaps the most beautiful.
The SP146 road between San quirico d'orcia, Pienza and Montepulciano is so beautiful...
So, from there(Around Buonconvento) you can do Volterra, San Gimignano, Sienna, Montepulciano, Montalcino, Pienza, San Galgano Abbey, the chianti region and even Massa Maritima on the western side in less then 1h30. Cortona as well going east.
You can even reach some great Umbria sites like Orvieto, Perugia and Arezzo within the same time frame.
Between 1:30 and 2 hours would be Todi, Gubbio and Assisi in Umbria, Pitigliano.
Hope this helps
Claude

Last October we spent 5 nights in Siena and planned to do a day trip or two. We did go to Florence one day by train, but instead we just kicked back and did not much of anything in Siena. There is a difference between 5 nights and two weeks, but we really enjoyed our experience. We stayed at Hotel Athena, which also provided free parking and was outside of the ZTL.

Buon viaggio,

My ideal for 2 weeks would be a few days in Florence, then a couple in Siena, then stay in an agriturismo with a car, somewhere on the "border" between Tuscany and Umbria and explore, including Assisi. Then end with a couple days in Orvieto.

How much time in Florence depends on your interests. If Renaissance painting, sculpture and architecture are right up your alley, you'll easily fill 3 days and still not see it all. If not, you can see the highlights in one day.

Most (all?) the historic town centers are ZTL's (limited traffic zones). You'll have to park outside them and walk or bus to the center. If you accidentally drive into a ZTL, the fine is huge. There are cameras so they will always catch you. There are no-entry signs, but you may not see them. If you are staying in a hotel in a centro storico, you can arrange for permission to drive in and out but you have to do it in advance.

I second Chani's suggestion. With 2 weeks, 3-4 bases would be ideal. Enjoy!

Are you spending two weeks in Tuscany including your time in Florence?

thanks all for the suggestions. We're leaning now towards a week in Umbria and a week in Florence near Sienna based on your ideas. We are more into food, wine and museum of the street than galleries, etc. Looking forward to turning off the GPS and getting lost for awhile too. Appreciate the tips about looking for the 'no entry' signs too.

We have done this 3 times, most recently for two weeks where we stayed in an apartment in Montepulciano. It was a wonderful base and it is a great town for restaurants and lovely sights. I prefer to stay in one place as a base, but you could rent for a week in two different areas. Generally you don't get a price break staying two weeks; that starts at a month and in this region rentals usually run Sat-Sat, so you could easily rent in two towns if you prefer.