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?
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.