1.5 days in Tuscan countryside, Need accommodations near freeway and itinerary


New member
I am posting this message under this thread as it most relates to accommodations. My husband and I are traveling to Italy from the end of August into September. We will be flying into Venice, spending a few days there, taking the train to Florence, spending two nights and one day in Florence, and then renting a car to go to the Tuscan countryside on Thursday morning for one and a half days/one night. After that, we will take the rental back to Florence and we will hop on a train to Cinque Terre.

All that being said, my question has multiple parts:

1. Since we are coming from Florence but heading back to Florence to drop off the car and go north, would it be better for us to start that Thursday off driving to Siena, spending much of the day there, and then working our way back and staying either in San Gimignano or Chianti?
2. Obviously since we don't have a ton of time in the countryside, it seems best to stay somewhere close to the Florence – Siena freeway so that we are able to move around easily. Does anyone have any good recommendations as far as farm houses or villas that are picturesque but that still accomplish the goal of being close to the freeway? I don't want to stay in a regular hotel; I've always imagined staying in a villa with a pool and that has a beautiful view of the hillside/Vineyard. My research so far has shown me that most of those locations are more inland, so I'm hoping to find one that is close to the freeway but also centrally located as a good place to base ourselves for the one night before making our way back to Florence.
3. Does anyone have any specific itineraries that you suggest we follow that would give us a good taste of the countryside in 1 1/2 days?

Thank you in advance!