Florence/Chianti region

Do you have a car?
It's been a few years since we visited, but we so enjoyed a trip to Brolio Castle, where chianti wine was developed by Barone Risacoli
https://www.ricasoli.com/en/castle/
We also had a bite in the restaurant (limited hours) and tasted some of their wines. Or you can go into the village for lunch and wine. Beautiful place.

Whether you have a car or are using public transportation is a crucial question since the rural Tuscany area is not served well by train.

Siena is the classic hilltown day trip from Florence for good reasons. You can experience the town, get some looks at the countryside and there are opportunities for wine tasting if that's one of your Chianti goals. If your interests are wine centric there is are pretty much hourly buses from Florence to Greve in Chianti which is a small town but is in the middle of some very good wineries.
Here is a map of public transportation in Italy: https://www.to-tuscany.com/travel-guide/travelling-to-tuscany/public-transport-tuscany/

If you have a car there are many towns - Greve in Chianti, Castellina in Chianti, Radda in Chianti, Gaiole in Chianti - that are all wine producing towns.
If your interests are more hilltowns here are RS recommendations: https://www.ricksteves.com/europe/italy/tuscan-hill-towns

If you have specific interests a tour is also an option and a good one if wines are your focus because tolerance for drinking and driving in Italy (and most of Europe) is nonexistent.

Have a great trip,
=Tod

There are lots of lovely towns to visit in the Chianti area...and yes, for most of them a car is necessary. However, you can visit Greve (one of my favorites) by bus from Florence. Would be a lovely day to enjoy the bus ride, walk around the town...lunch and shop. And then no worries about driving winding roads back.

Before I started renting, I have stayed several times at Hotel Il Bargellino at Via Guelfa 87 (not far from the SMN station). Since I usually travel solo, it has a lovely large terrace for guests to mingle or just relax with some wine etc. Enjoy your travels!

Thank you everyone! Great tips

We did a "drive around Chianti" day last month, starting from Siena. (While we enjoy a good glass of wine with dinner, we had no interest in visiting wineries.) The drive itself was quite scenic, although not quite as scenic as the area around Pienza. On our drive we stopped at Gaiole which is a beautiful village. However, it is quite small and you can easily see all of it in less than an hour. Our next stop was Radda which was our favorite stop of the day. Lots of shops and restaurants there and several little side streets to explore. Our final stop was Montefioralle, a mostly deserted town about a mile or so west of Greve. Walking around there it felt like we had stepped back in time 700 years. Both Radda and Montefioralle required steep climbs although not as much as towns like Volterra or Cortona which are also doable from either Florence or Siena.