Hy husband & I will be in Florence for 6 nights with a company sponsored trip. But we are going 3 days early to stay outside San Gimignano. We will be renting a car for the 3 days. Question - Our plane lands around 9:20 a.m. & my plans are to drive down 222 on the way to our B&B & go through the Chianti region & stop for lunch. Any suggestions for a cute, quaint place to sit outside & enjoy the scenery? Also, do you need reservations to stop at a winery to sample wines?
Check out Castello di Verrazzano. We went there for lunch, wine tasting and a short tour of the winery. You do have to request the english speaking tour, unless you want to wing it in Italian. http://www.verrazzano.com/
I would suggest stopping at Greve in Chianti for lunch. We did this last year on the way from Florence to Siena. It has a beautiful market square wih several places to eat. Also if you have time on your way south visit the beautiful US military cemetary just outside of Florence