3 weeks in Chianti Country

On my first villa rental in Tuscany we had 7 couples, and having three medium sized cars was wonderful. We quickly realized our travel styles weren’t all the same, and having multiple cars freed friends to go slow or go-go-go as the spirit moved them. I know this doesn’t answer your question, but just a thought. I’m sure plenty of people will be chiming in on the headaches of parking a van in the average Tuscan village.

In earlier threads on this topic (rental vehicles for large groups), it has been mentioned that a special driver's license may be required for large vehicles. in some countries. I don't know what the rules are in Italy, but as the number of passengers increases, at some point the driver(s) may need the Italian equivalent of a chauffeur's license. Something to check out before deciding a single large vehicle is the way to go.

Other frequent warnings involve the presence of speed cameras on Italian highways and camera-enforced ZTLs (no-entry zones) in and near the historic areas of many towns and cities. No warnings will be given if you trigger one of the cameras, so some tourists keep breaking the same rules over and over. When that happens the rental-car company charges an administrative fee (one per ticket) to the renter's credit card, and at some point after that the actual traffic tickets start to arrive. It can make for a very unpleasant and costly surprise after the trip is over. To avoid this it is essential that all potential drivers familiarize themselves with the Italian rules of the road.

Also be aware that the average European vehicle is quite small, and your parking options at some destinations may be quite limited if you are driving a large van.

I am unable to determine the location of the villa. Can you give us the name of the nearest town?

We have rented a place for the past 6 years (not 2020) between Florence and Siena for a month each year. We have had from 3 to 12 people with us each week during the years. We too have found it’s better to have several cars so people can do what they want and get to and from Rome or Florence airports.
We also rent a van with a driver for touring wineries . Pre-Covid the van would hold 8 - this year there are limitations so we are using 2 vans. We have also found that 8 is a good number for us to have.

It is easy to drive in Italy - especially if you have a navigator sitting next to you. You do have to be careful in cities - the ZTL zones. We will park at a train station near our villa and train into Florence or find a parking lot on the outskirts.
You do need to watch the speed limits - we have gotten those tickets a year later and a charge from the rental company.
On another note - if your villa has access to a cook, do that a couple nights. Easier than 10 people in a restaurant and more relaxing for you as the person in charge!

5 couples means two vehicles, as you cannot drive anything larger than a 9-seater van (driver included) with a normal license, and such a van will not have enough space for 9 people's luggage.
Plus, as others have said, it is better to have at least two vehicles for such a long trip: more freedom for people!
Even three vehicles (perhaps 2 large cars/minivans where 5 people fit comfortably + a smaller one) would be better in my opinion.

You've gotten some great advice. I totally concur multiple cars will be much better than one large van.

We loved driving around in Tuscany and had no problems. I strictly adhered to the speed limits, there's zero tolerance and they use automated cameras. ZTLs are usually well marked. Assume that anywhere within the walls of a hill town like Radda and San Gimignano is ZTL. We opted to leave the car at our agriturismo and take the bus for our visit to Florence, which was a great decision.

Finally, though we rarely saw police, it would be a good idea to have a designated driver if you plan to do wine tastings. They've really cracked down on drunk driving and their limit is so low that a second glass of wine might put you over. I really liked the idea of having dinner at the agriturismo instead of going out. That's what we did. Since we stayed at a winery, we could enjoy ourselves and not have to worry about driving.

Have a great time!

Thank you for all the responses and advice. We are renting 2 vehicles. More questions to come.

We rented three cars for our large group in Chianti.
We have traveled to this region four times, a favorite destination for us.
You must visit Panzano, both upper and lower sections, Radda, Siena and Gaiole, all in Chianti. We did our grocery shopping in Gaiole when we stayed in Panzano.
Farther afield you can visit Pienza and Montalcino or Volterra and San Gimignano. Florence, of course.