From the medieval towers of San Gimignano through the Chianti hills — with an honest note about how far to push it in a day.
San Gimignano → Castellina in Chianti → Greve in Chianti → Montalcino: about 78 miles and roughly 3 hours of driving in total, not counting stops or tastings. You can see this route with turn-by-turn directions on our Tuscany region page.
Start among San Gimignano’s medieval towers, home to Vernaccia di San Gimignano — Italy’s very first DOC wine, back in 1966, and a DOCG since 1993. Panizzi, right in town, is a good first stop.
The heart of Chianti Classico, and the densest choice on our map. Around Gaiole and Radda: Castello di Ama; Ricasoli’s Castello di Brolio, whose castle grounds are open daily from March to December without booking; Badia a Coltibuono, an 11th-century abbey with a restaurant and cellar tours; and Castello di Volpaia, a whole medieval village turned winery. Marchesi Antinori’s estate is a short detour from Greve, and Fontodi in Panzano takes visits on weekdays only. Apart from Brolio’s grounds, all of them require booking well ahead.
Honestly, often yes. Montalcino — Brunello country, not technically Chianti — is roughly another hour south of Greve. If you’re already tasting wine at a relaxed pace, treat this leg as a bonus for a very early start, not a given. Pressed for time, end the day at Castellina or Greve instead.