Riding to school growing up was like driving through an idyllic painting. Every morning, my father made the 40-minute trip from our house in the countryside to my school in Florence. Gazing out the car window, I could see an infinite sequence of vineyards and olive groves blanketing the rolling hills all around us, topped here and there with a lonely farmhouse at the end of a cypress-lined dirt road. Yes, what I’m describing sounds like every romanticized depiction of Tuscany you’ve ever read about or seen on TV, but I can assure you that these portrayals are all true. I was one lucky kid to grow up in Tuscany, but the angsty, sulking teen on those 7 a.m. car rides to school took it all for granted. It was only when I moved to the U.S. for university that I realized how much I missed those landscapes. When I’d come back during breaks, on the drive home from the airport, my eyes would scan the scenery in awe as if for the first time. Once home, I’d run up to my room, throw open the window and snap a picture of what I considered the most beautiful view in the world: a vineyard, a lonely house, a row of cypress trees. Then, without fail, I’d post it on Instagram to announce I was finally home. Home in Chianti.
Of course, most people know il Chianti for its wine, which has become one of the most famous in the world. Glasses of the dry, tart ruby red are sipped at dinner tables everywhere. And while a simple Chianti can be delicious, when the word “Classico” appears next to it on the label, you have something far more special. There are several differences between Chianti and Chianti Classico wines, but one of the biggest is their area of production. Within the larger Chianti area lies the Chianti Classico, a stretch of land between the provinces of Florence and Siena that spans 70,000 hectares. This territory contains the municipalities of Castellina in Chianti, Gaiole in Chianti, Greve in Chianti, Radda in Chianti and parts of Barberino Tavarnelle, Castelnuovo Berardenga, Poggibonsi and San Casciano Val di Pesa. You may be familiar with their amazing wines, but you may not have explored the many medieval towns scattered across them. Some of them barely number a thousand inhabitants, but their small sizes only increase their charm.
If you’d like to visit, here is a list of some of my favorite towns and hamlets of Chianti Classico, along with some recommendations on what to eat, drink and see. Buon viaggio!
Castellina in Chianti
Castellina, one of the better-known Chianti towns in the province of Siena, sits perfectly perched on top of a hill. On a quiet February afternoon, strolling through its empty streets, I ducked into Via delle Volte, a vaulted tunnel on the side of the village and the town’s most characteristic feature. Alone inside the dimly-lit tunnel, I listened to my steps echo off the ancient stones. I felt like I was in another time. On the inner walls, a series of doors lead to restaurants, shops and wine cellars. The small openings along its outer wall, vestiges of medieval wars gone by, look out onto the vineyards below. If you’re looking for a dose of culture after walking through the tunnel, head to the Museo Archeologico del Chianti Senese in the castle-like fortress at the center of town. Make sure to visit Castellina on an empty stomach so you can have one of the best meals of your life at Taverna Squarcialupi, which also has a wine shop and cellar. Everything on the menu is simply divine, especially the pecorino tart accompanied by a wine-soaked pear.
Radda in Chianti
Radda is a short drive from Castellina along a serpentine, forested road and is a pretty jewel in the Chianti crown. I suggest arriving here right before sunset, when everything is drenched in the light of the golden hour. On my last visit, I walked around the perimeter of the town and sat on one of the benches to take in the magnificent view. The calm atmosphere made me want to crack open a book or write a journal entry or meditate. I chose meditation. As you walk through its well-kept streets, make sure to stop in Piazza Ferrucci and check out the Fontana del Leone, a lion-headed fountain built in 1926. Radda is one of the most prolific wine-producing areas of Chianti, so you cannot leave without a visit to a winery. At Colle Bereto, each bottle I tasted was better than the last, but rather than taking home a Chianti, I left with their excellent Pinot Nero to save for a special occasion.
Barberino Val d’Elsa
Down the road from my hometown of Tavarnelle Val di Pesa, Barberino Val d’Elsa hugs the hillside. I’ve passed through a thousand times, but the spectacular scenery never gets old. Enter the town through the tall medieval archway and make your way to the terrace in front of the church of San Bartolomeo to admire the tapestry of vineyards and olive groves spread below. If you happen to find yourself in Barberino at the beginning of May, be sure not to miss the flower festival, a colorful celebration during which gorgeous flowers and plants line the streets. Located in the pine grove just outside the center of town, L’Archibugio has been one of my family’s favorite restaurants for years. If you’re in the mood for a great pizza, this is the place to go.
Badia a Passignano
Although not a town, I have included Badia a Passignano in this list because it is breathtaking in its magnificence and beauty. Nestled in a cluster of cypress trees just outside of Florence, Badia a Passignano is a Benedictine abbey dating back to the year 395 A.D. with only a handful of houses around it. To this day, the Antinori family ages one of their most notable Chianti wines in the ancient cellars beneath the monastery. Taking the narrow two-way road to Badia by car can be daunting, but as soon as the abbey comes into view, the drive suddenly becomes worthwhile. Though tiny, this hamlet certainly has no lack of restaurants. Dine at l’Antica Scuderia for a meal of Tuscan specialties or on a sunny day, sip wine and snack on charcuterie on the terrace of Bar Divino, overlooking the local vineyards. If you’re looking for a unique winery off the beaten path, visit Poggio al Sole, located in the forests behind the abbey. Their white sangiovese is fantastic.
A quick drive or stiff hike from the larger town of Greve in Chianti, the tiny stone village of Montefioralle is tucked away in the hills like a stolen gem. One of the most beautiful hamlets in Italy, Montefioralle counts only 79 residents. On my visit, the only two restaurants in town were closed, but I wasn’t there for the food, just a dreamy stroll through its charming streets. As I was leaving, I felt as though I was stepping out of a fairy tale. Try to find the house with a small wasp relief above the door: this is the rumored birthplace of explorer Amerigo Vespucci (“vespa” means wasp in Italian). If your stomach is grumbling after your visit, Greve is full of great restaurants. I stopped for an exquisite steak tartare at Antica Macelleria Falorni in the main piazza, but if it’s something sweet you’re after, sit in the shade of Pasticceria Chianti to enjoy a pastry and a coffee. Down the road from my hometown of Tavarnelle Val di Pesa, Barberino Val d’Elsa hugs the hillside. I’ve passed through a thousand times, but the spectacular scenery never gets old. Enter the town through the tall medieval archway and make your way to the terrace in front of the church of San Bartolomeo to admire the tapestry of vineyards and olive groves spread below. If you happen to find yourself in Barberino at the beginning of May, be sure not to miss the flower festival, a colorful celebration during which gorgeous flowers and plants line the streets. Located in the pine grove just outside the center of town, L’Archibugio has been one of my family’s favorite restaurants for years. If you’re in the mood for a great pizza, this is the place to go.
Panzano in Chianti
While every town on this list has spectacular views, Panzano offers one of the most iconic in all of Chianti. Just outside the center of town is a large statue of the Gallo Nero–the Black Rooster, symbol of the Chianti Classico–marking the famous lookout point. Stand next to the rooster. Sprawled in front of you will be an infinite Tuscan horizon that will remain etched in your memory long after you leave. At the top of the steep hill leading into the village, the Santa Maria church, a blend of classic and modern architecture, overlooks the town. And of course, a visit to Panzano wouldn’t be complete without a meat-fueled meal at the world-renowned Macelleria Cecchini. Make sure to devour a juicy steak there and ask the owner Dario to entertain you with a verse from Dante’s Divine Comedy.