We ( A multi-generation group of ten) have three nights in the Florence/Chianti area. Would you use Florence as your base and take day tours from there? Or, would you use an Inn in a small village (Radda) in Chianti? I'm assuming the tours will include a day trip to Assisi, maybe a tour that visits wineries/cheese makers, and the Ferrari museum, or perhaps a cooking class--don't know yet. I've started working with a destination manager because it is easier to figure out transportation etc for ten with some help. He's helping us with hotels and vans and I'm booking about half of my own tours.

The Florence option is more expensive, but manageable. I wondered if, since we were staying in Venice and Rome the other nights, a village setting might be better. However, Florence would offer ( I assume) more late afternoon/evening post-tour options and we are a large, diverse bunch.

Thanks for taking your time and sharing your thoughts.

Radda in Chianti is a pretty village with a good choice of places to stay. We enjoyed staying at Relais Vignale. It is well located for winery visits. It depends on how much in Florence your group wants to see. I have stayed in Florence and also have visited it on a day trip.
Your Assisi comment seems out of place. It is in Umbria, to east of Tuscany. If knterested in staying in Tuscany and visiting Assisi, Cortona would be a better location. It could be visited from Radda but a long day;better to visit Siena from Radda. Look at Rt.222, the famous Via Chiantigiana.

Three nights means you have only two full days, but you've listed 3-4 destinations/activities. Does that mean the group will split up and follow their own interests? Did you not want to see anything at all in Florence??

FYI, the drive from Radda to Maranello is nearly 3 hours each way. Florence would be closer. Radda to Assisi is over 2 hours each way. No matter how amenable and cooperative everyone in your group is, it will take more time to move and sightsee with a group of 10 than you can imagine.

You won't fully appreciate the contrast of small village v. big cities if you're driving long distances the entire time. Is the lodging you've selected within walking distance of Radda?

There are direct trains from Florence to Assisi. It's a slow, regional train that passes through nice countryside, taking about 2 1/2 hours each way. Tickets cost €16 one way, and there is no discount for advance purchase, so you should just buy the tickets at the train station. The same train stops in Cortona, which is indeed much nearer to Assisi, but the town of Cortona is not very near the train station.

If you catch a direct 8:02 train, you'd be in Assisi by 10:49. You have to take a bus up from the station to the town. There's a direct return train at 17:21, getting to Florence at 19:54. This would give you around six hours in Assisi.

Driving takes about the same amount of time.

Radda is closer to Assisi than Florence is, but you'd have to get a private driver to take you there, I would think. The drive would take about 2 hours.

Thanks for your help. Sorry for the delayed response. I took your advice and decided to stay two nights in Cortona. We'll stay two nights in Florence too.

So appreciate the input.