Recommendations for Day Trip (by car) from Florence -- within an hour please?

San Gimignano is a great tuscan town to visit and ine.

A loop for you.
Start from San Gimignano, then move on to Monteriggioni, from there go to Castellina. Castellina is in the Chianti. From Castellina drive the Chianti road back to Florence. Stop at wineries if you wish.
Plot this itinerary on google maps.

Another nice day trip would be Volterra, but you can’t do all of the above and also Volterra, since Volterra is a bit of a drive west of Monteriggioni while Castellina and the Chianti is east of Monteriggioni.

Thank you. I have been to San Gimignano but that was back in 1999. I know it has become very popular with tourists so I was going to avoid it because RS recommends going there either early (which is unlikely) or after the crowds dissipate (5 pm). But, I will do a little reading and see if it is worth the hassle. I very much appreciate your advice.

I like Roberto's loop suggestion.

I have another suggestion, but it is based on you being able to take a little more time and being able to return at night.

Part 1 - Florence to Greve. Leave Florence 8:00. Drive down the famed Chiantigiana (SR222) road. Arrive Greve 8:45. Visit this charming town in the morning.

Part 2 - Take winery tour and do wine and food tasting at Castillo di Verrazzano. This winery is 10 minutes outside of Greve. The winery is gorgeous and the tour is wonderful. The food and wine tasting is amazing. The problem is that it will take a minimum of 2 1/2 - 3 hours for the tour and tasting, but you will only need a light snack for dinner! You can always skip the food and wine tasting and just do the tour with the wine tasting at the end.

Part 3 - Drive to Castillina If you leave the winery at 2:30, you can be in Castillina at 3:00. From here you have two options, based on how much time you want to spend and how late you want to return to Florence.

Part 3, Option 1 - Spend as much time as you like visiting Castellina, then drive back to Florence. Depending on your route, you are 45 minutes - 1 hour from Florence.

Part 3, Option 2 - Castillina to Volterra. If you can possibly spare the time, this is what I recommend. It's a one hour drive through some spectacular scenery. Spend an hour in Castillina, then hit the road @4:00. Arrive in Volterra @ 5:00. Wander around in town until an hour before sunset, then go out the gate to the promenade to the west of the city. From there you will be treated to a spectacular sunset. There's a fantastic view of the city and the light constantly changes. The townsfolk come out to the promenade in the early evening and you'll be able to mingle with the residents. We didn't plan on staying that late, but the sunset was so amazing, I stayed and photographed until dark.

The drive back from Volterra to Florence is ~1 1/2 hours. I know this is further than you planned and you probably wouldn't get back until after 10:00, but you will have packed in the heart of a Tuscan experience in one long day. My Facebook home page image is a photo I took at Volterra. Every day I think about that magical time. Volterra and Verrazzano are two of the standout moments of our 10 days in Tuscany.

WOW! Thank you for the thoughtful response. This looks interesting and I will run it by my daughter. I don't think we would be able to get out of Florence quite that early. Returning late is not a problem. I really like your first option but I think my daughter would be interested in seeing Volterra. I also have a friend who rented a car and stayed in Poggibonsi last year; I was going to check with him to see what he recommended in the area.

We decided to drive to Greve, then to Castellina, then to Siena (arriving in Siena in the afternoon, when we hope to have to deal with less crowds) so that we can visit Montepulciano and possible Pienza on our drive to our next destination (Assisi). I really appreciate the assistance with my trip planning.