You can make Florence to Siena in about 1.5 hours, but the people who love this drive never do it in one straight shot. At around 45 miles on SR222 Chiantigiana, it is short enough to start after breakfast and long enough to earn a night somewhere memorable among the vineyards.
Open this route in XCRSNLeaving Florence
Aim to clear Florence before the morning rush, or after it, never in it. Fill the tank on the edge of town where prices usually drop, set the playlist, and settle in for the first 19 miles to Greve in Chianti.
The headline stop on this route is Chiantigiana road through the hills. Leave real time for it; it sets the tone for the whole trip.
Greve in Chianti
Greve in Chianti sits about 19 miles in. It makes a good spot to stretch, eat something that is not from a gas station, and swap drivers.
Nearby, Castello di Brolio is worth the short detour if the day is going well.
Castellina in Chianti, the last stretch
Castellina in Chianti sits about 30 miles in. It is the natural place to stop for the night: hotels are plentiful, rates beat the big-city ends of the route, and you wake up with the hardest miles already behind you.
Rolling into Siena
The final 15 miles always go faster than you expect. Save a little energy for Piazza del Campo in Siena; it is a fitting finish.
By the end you will have seen Chiantigiana road through the hills, Castello di Brolio and Piazza del Campo in Siena, and you will understand why this corridor is a classic.
When to go and how to pace it
One night is the sweet spot. Greve or Castellina in Chianti, Italy is where most people stay, so book ahead on summer weekends.
Check live gas prices along SR222 Chiantigiana before you go; they can swing a lot from one state or county to the next. XCRSN prices every leg for your exact car.
