I'll give you some pieces of advice for the most fruitful and enjoyable Tuscany wine-tasting experience.
Tuscany is bigger than it looks
This region, which is known to have given birth to the best Italian wines, is pretty big. Everything looks close right around the corner as the crow flies, but you can’t be fooled by that.
So it will take a long time to get from place to place.
Go Slow
With hundreds of wineries available you may feel the need to visit as many as possible. That isn’t practical. Instead of driving like in a tour de force, think of it more like a slow wine crawl. Don’t ask us to plan ten spots in one day, aim for three. Two would be ideal. Everything in Italy is done slowly, you won’t have time to experience and taste wine if you rush through tours and tastings and drive all over the place. We highly recommend spending more time at each winery and less time in the car.
Remember that Florence is a good place to base yourself for touring the Chianti Classico area, and Siena is a nice base for exploring and tasting Brunello, Vino Nobile, and Rosso di Montalcino. So let's first focus on the wine-growing region and then ask to plan a private wine tour.