Tuscany

Tuscany is a big region. What places do you want to visit. That would help provide a central base. Will you be driving or just using the train.

We're staying for a week in early October (a month from now) at a small place outside Castagneto Carducci, a hilltown, close to the ocean, and very near a major ancient Estruscan site. It's 5 miles inland, about 30 miles south of Livorno, 60 miles south of Lucca, and about 75 miles southwest of Florence, so a bit away from some of the busier places in Tuscany. The owners do cooking classes (single or for even weeklong), and rent out 2 apartments above their home. If you're looking for a hotel or B&B that serves breakfast, this probably won't work, but you can fix your own in your kitchen - recipes downstairs. I can give more details if you're interested.

You need to focus on what part of Tuscany you are interested in. As others have stated, it is a large area.

More detail appended by edit to original request. Thanks so far, everyone!

You need a car to enjoy Tuscany. Pick it up as you leave Florence. You will miss a lot and waste time if you just use public transportation. We usually stay in the Chianti area , near Siena… Castellina, Panzano, Radda. We also have stayed in Cortona.

Umbria is wonderful too. We stayed in Spello.

Driving in Tuscany is easy and since it’s very countryside-like, there’s no stress like in the bigger cities. Renting a car also gives you freedom to move. I’d pick up and return a car in Florence (or drop in Siena, Cortona, or on toward Rome if heading there). I’d base in Montepulciano. Rick has good recommendations in his book. You’d be striking distance to many lovely towns - Montalcino for expensive wines, Pienza for beautiful scenery and cheese, Cortona for scenes of work a day Tuscany, and all the lovely places in between. It depends on your budget as to where you should stay. Most of Tuscany is made up of small old towns. Florence and Siena are large but Siena gets sleepy at night. Volterra is biggish but sleepy at night. San Gimignano is also sleepy at night. If you want a city, stay in Florence and day trip from there. You might find a hotel with parking so you can move in and out as you please. Driving to and from Florence each day means a driver cannot enjoy the wine paired with the wonderful food. I found an itinerary with overnights throughout Tuscany allowed targeted experiences - Florence, San Gimignano, Volterra, Montalcino, Cortona, Montepulciano, Siena, and it was amazing.

I would suggest this site on Tuscany. https://www.visittuscany.com/en/

Thank you, Everyone!