When one dreams of Italy, dotted with cypress trees and sprawling vineyard fields, one is often dreaming of Chianti. This screensaver-worthy region in Tuscany is known for its wine region and the ancient highway that connects Florence to Siena, the Chiantigiana (SR222).
Running through the center, like a main artery, Chiantigiana, is often called the Stada del Vino (the Street of Wine) because it courses through the heart of Chianti.
Certainly, there are other wine regions in Italy—the celebratory bubbles of Franciacorta, the organic, pristine fields of Sicily, and so many others-but there is truly something special about Chianti. After all, that’s why it’s so famous!
This guide will bring you on a journey through the idyllic Chiantigiana. The road, if you were to drive straight through without stopping, would take you around 2 hours in total. In order to really enjoy the delights of the Chianti region, you must take things slow.
Florence
Your journey starts in Florence and travels south. Remember, the Chiantigiana used to be the single road connecting Florence to Siena.
Your first stop will be in Greve in Chianti. Consider this town the welcome room leading into the rest of the Chianti region. It’s your entry point, your introduction. In true Tuscan fashion, the town was formed around the 1500s, yet modern residents seem happy to live within the weathered, ancient structures.
Greve in Chianti
The town’s history is an interesting one. It was originally the market center for the nearby Castle of Montefioralle, which I also highly recommend you check out. You can take a quick tour of the castle and enjoy its beautiful vistas.
Greve in Chianti was also in a strategic location—not only placed upon the Chiantigiana, but two other roads leading to Valdarno and Val di Pesa. For the commercial affairs of the Middle Ages, this was a perfect spot to trade and do business with passing travelers.
Honoring that commercial spirit, an outdoor market takes place every Saturday in the town square, where vendors come from nearby farms to sell meat, cheese, and produce. Speaking of produce, this is a prime spot in Tuscany to go truffle hunting.
Montefioralle
I mentioned the Castle of Montefioralle earlier, but there’s also another reason to visit the nearby town of Montefioralle. This fortified village was the birthplace of Amerigo Vespucci. You know, the guy who the Americas were named after?
See if you can find his ancestral home on the main street. Above the front door, there is still the family coat of arms and a wasp.
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Castello di Verrazzano
Meandering the cobblestone streets of an ancient village certainly does make one thirsty. If you’re ready to sample Chianti wine, make your way over to Castello di Verrazzano, a winery open for cellar tours and al fresco dining.
Panzano – Dario Cecchini
I hope it will be time for lunch by the time you arrive in Panzano, because Italy’s most famous butcher is there to serve you some meaty delights of Tuscany.
He’s serenaded guests. He’s made appearances on Netflix. He’s a butcher and animal lover. And of course, he owns a few restaurants where you can get a glimpse (and a taste) of that chaotic combination.
The place you want to go is Antico Macelleria Cecchini, a little shop front with a hidden restaurant set in the back. Don’t worry, you’ll have no trouble locating it, as there is always a line of people enjoying a glass of house wine out front while they wait for an open table.
Now, About That Wine
Wineries in Chianti are vast. You can drive in any direction off the Chiantigiana and end up at one. All this competition means that it’s very hard to make it as a wine business here without really good wine.
Enthusiasts will, of course, tell you that there are good and bad wineries in Chianti. Frankly, I think you’ll have a hard time finding a bad glass of Chianti. So, it begs the question, how do you choose which one to visit?
I have a few suggestions.
Casa Chianti Classico
Taking a slight detour off the Chiantigiana will bring you to Casa Chianti Classico. It’s set in a former convent, and you can come here for guided walking tours through the vineyards and enjoy their patio wine bar.
Poggio Amorelli
My favorite spot in Chianti is Poggio Amorelli, a family-run estate found at the end of a dirt road. Their cellar tours are interesting, but their restaurant is absolutely beautiful—designed in the traditional Italian farmhouse style.
The food here is great, and the wine is even better. They don’t distribute their wine bottles internationally, so unless you want to order a shipment to your house, you won’t be finding these bottles in stores anytime soon.
Lamole di Lamole
Lamole di Lamole is a feast for the senses. Picture yourself finishing up a cellar wine tour at a tucked-away away hidden gem vineyard. No tourist lines and no price surging; just you and a few other curious, wine-obsessed hopefuls on an intimate tour.
After finishing up, a picnic is laid out for you in the middle of the grape fields, and you enjoy the most picturesque lunch, perhaps of your life.
Castellina in Chianti
As your final stopping point on the Chiantigiana, drive into Castellina in Chianti, a village seemingly sprouting from the top of a hill. It sits in the center of rolling vineyard hills and is surrounded by pointed cypress trees.
Day tripping through Tuscany on the Chiantigiana allows you to see the rolling vineyards as you pass, but now is a great opportunity to experience them up close. I recommend you park in Castellina and rent bikes for a moderate bike ride to the nearby town of Radda. Both towns are on a similar Ridgeline, so you won’t have too many inclines during the 35-minute ride. Meanwhile, you’ll enjoy the stunning sights of rural Tuscany and can stop anytime you’d like to explore on foot.
FAQs for Your Consideration
When is the best time to visit Chianti?
The best time to visit Chianti is in October. This is after high season when the majority of tourist crowds have left, and the weather is milder. You can expect hot days and cool nights.
Also, this is when the Chianti Classico harvest takes place, and many wineries open up their cellars. You can also find annual sagre, or harvest events, taking place in the area.
How long is the Chiantigiana?
The Chiantigiana (SR 222) is 70-77 kilometers (about 43-48 miles) and goes from Florence to Siena.
How long does it take to drive the Chiantigiana?
If driving without stopping, it will take you about two hours to drive from Florence to Siena on the Chiantigiana. It’s even faster to take the Raccordo Autostradale Firenze, another highway that connects the two cities in about an hour.
Can I bike on the Chiantigiana?
Yes! In fact, there are major cycling communities that ride all through the Italian countryside, including on the Chiantigiana. Although you will have to share the road with other drivers, this is a truly picturesque bike ride.
Is the Chiantigiana safe to drive?
Yes, generally the Chiantigiana is safe for drivers, but you will need to be cautious about your speed. There are a ton of speed cameras (autovelox) that will send you an electronic ticket if you go 5km above the speed limit, but to be honest, it’s warranted on the Chiantigiana.
The road takes hairpin turns and can become very narrow, very quickly. If you aren’t experienced on the road, it could turn dangerous if you’re driving too fast.
