Driving from Tuscany to Florence

From where in Tuscany? It’s a large area ( Florence is in Tuscany)

Perhaps it is the reverse.

We stayed in Siena for six nights and loved it.

San Giminano is great.

https://www.discovertuscany.com/siena/what-to-do/day-trips-from-siena.html

Tuscany is a region larger than Massachusetts

Florence is a city within Tuscany (the capital of Tuscany in fact).

So your question is like asking for recommendations driving from Massachusetts to Boston.

We drove from Rome to Florence stopping at Pitigliamo then staying near Pienza in an agriturismo. We spent several nights there visiting towns including Montepulciano. We also spent a few nights in Chianti near Greve in Chianti.

Until OP tells us from where in Tuscany

https://www.ricksteves.com/europe/italy/tuscan-hill-towns