I'll around in Tuscany, Florence and Siena specifically, for about a week and a half in late September and early October. Any recommendations or suggestions of where to go and things to try?
Check out Fattoria La Vialla in Arrezzo, Casaloste in Panzano, Querciabella in Greve in Chianti, Isole e Elena outside of Castellina in Chianti, Felsina in Siena, Castell'in Villa outside of Siena/San Piero.
In Florence, check out Enoteca Pitti Gola e Cantina, across from the Palazzo Pitti. They have a great list and some older vintages by the glass.
In Greve in Chianti, Enoteca Falorni has 100+ wines by the glass so you can taste a lot of different producers from the region.
Siena has a lot of great wine-centric restaurants — some of my favorites were Osteria Le Logge, Salefino Wine and Cuisine, Bagoga Grotto di Santa Caterina, and L’Orto e un Quarto.