maybe 2 places in Tuscany is more convenient...
Ciao Alkoch97,
Whether you want to stay in 1 or 2 places while in Tuscany depends on whether you feel more comfortable getting to know one area and sort of "settling in" into one place or if moving between the two places is fine with you.
If you found two places you like where you can divide up your stay, the main advantage would be that you can cut down on driving times between places you want to see. So if you don't mind moving between one and other, go ahead and stay in both.
If you stay near San Gimignano, you can visit
San Gimignano,
Volterra,
Certaldo and
Colle Val'Elsa which are the main ones in that area.
Once you stay in Greve, visit all the small villages in
Chianti (Castellina, Greve, Radda, Panzano, Gaiole - they are small so quick to visit) and
Siena. If you have time, take a day trip to the area south of Siena into the
Crete Senesi and
Valdorcia (both are areas). Visit
Montalcino and
Montepulciano just to drive the roads in between which are very scenic (these are in the Valdorcia).
If you stay in two places, you'll enjoy driving through the Tuscan countryside but not spend too long in the car to get places. If you were to stay just in one place for the 5 nights, it would still be okay but driving time would get longer. Distances are short but the smaller roads are mostly 2 lanes where max speed is 50-70 kph (30-45 mph). The Firenze-Siena roadway allows for speeds up to 90 kph (56mph) that you can sometimes take if you want to get someplace faster, depends on your day's itinerary, but the view isn't as nice.
Once you are in Florence, return the car first thing since you don't really need it once you are in town. If you want to make it out to Pisa to see and climb the Leaning Tower, you can take the train from Florence and spend at least half day there. It is about an hour train ride. Spend the rest of the time enjoying Florence and all its sights.
Hope my suggestions are helpful!
