Italy’s Charming Wine Region: Greve, Castellina & Radda in Chianti
As you drive away from the bustling streets of Florence, you’ll be greeted by the serenity of the Tuscan countryside. Along SR222 Chiantigiana, one of the most scenic roads in Italy, the Tuscan landscape unfolds into green-golden rolling hills and soon reveals vineyards that signal your entry into the Chianti region. You’ll be able to pair excellent Chianti Classico wine with equally delicious food, experience the warmth of Chianti locals, and daydream as you immerse yourself in this part of Italy’s medieval charm.
Understanding Chianti’s Wine Legacy and Region
The Chianti region, Italy, is renowned for its rich wine legacy and beautiful landscapes. Chianti Classico, a hallmark designation within this region, refers to wines made predominantly from Sangiovese grapes, known for their vibrant acidity, cherry flavors, and earthy notes. As you explore, you’ll discover rolling hills dotted with vineyards that have been producing Chianti Classico for centuries, embodying the region’s rich history and tradition.
Scenic Trip on SR222 Chiantigiana: Exploring the Chianti Classico Regions
Wander Around Greve in Chianti
In Greve in Chianti, you can start by exploring Piazza Matteotti, which is filled with local shops, cafes, and a lively market. Next, visit the Church of Santa Croce, a historic site dating back to the 11th century, known for its medieval architecture across centuries. Walk around, window-shop, and leisurely enjoy the village’s charming atmosphere.
Just a 20-minute walk from Greve in Chianti, you’ll find Montefioralle, one of the region’s most ancient and beautiful hamlet. Once called “Monteficalle” after the fig trees that once grew around it, this village dates back to 1085 and boasts charming stone houses, narrow streets, and the beautiful Church of Saint Stefano.
Walk Through Memory Lane in Montefioralle
Although the Vespucci family owned a house here, there is no historical evidence that Amerigo Vespucci was born in Montefioralle. When I asked a local though, he did mention that Vespucci might have spent some time there as a child.
Panzano in Chianti: The Santa Maria Church and Its Surroundings
At the outskirts of Panzano in Chianti, near the Church of Santa Maria Assunta, you can enjoy stunning views of rolling hills and lush vineyards.
The Church of Santa Maria, located beside the castle, was reconstructed in the 19th century on the foundations of an older church. It features a 14th-century Siennese Madonna and Child, attributed to Botticini. In the oratory to the right of the nave, you’ll find an Annunciation attributed to Michele di Ridolfo del Ghirlandaio.
Antica Macelleria Cecchini: A Must-Visit for Meat Lovers
In Panzano, you can enjoy the Tagli Cecchini menu dining-in, featuring Dario Cecchini’s unique bone-in and boneless cuts. They also have a Panini food truck daily from 11:30 am to 3 pm, which I missed by 30 minutes 😢.
Explore Castellina in Chianti: The Cobblestone Delight
After arriving in Castellina, I instantly fell for its charming, unpretentious cobblestone streets and buildings. You can explore La Rocca, which has stood since the 15th century, and enjoy stunning views of the Chianti Hills. Just a short walk away, stroll along Via delle Volte, a covered walkway built by Brunelleschi to resist gunpowder explosions.
And don’t miss the neo-Romanesque Church of San Salvatore, which features a fresco by Maestro di Signa and a wooden statue of Saint Barnabas.
Relax, Unwind & Dine in Radda in Chianti
In Radda in Chianti, you can explore historic streets with charming cobblestone paths and tunnels. Notable sights in town include the Palazzo del Podestà and the Propositura di San Niccolò. If you’re planning to visit multiple wineries like Castello Brolio and Albola, Radda in Chianti is a great place to stay overnight after exploring the Chiantigiana.
If not, you can head west to visit the medieval marvels of San Gimignano and Volterra or head south for a Val d’Orcia road trip through Southern Tuscany via the SP2 and SP146.
If you’re staying for dinner, I highly recommend dining at La Bottega di Giovannino. The Pasta alla Giovanino is a daily specialty that changes every day, and you can pair your dish with a fantastic selection of Chianti Classico wines.
The owner is very welcoming, and the family restaurant’s charm makes you feel like you’re dining with a local friend. This is definitely one of my best dining experiences in Italy. Plus, if you stay the night, you can fully enjoy your wine pairings abundantly without the worry of driving 😏.
The Charming Small Village of Volpaia
From Radda, it’s about a 20-minute drive to Volpaia, a picturesque medieval hamlet known for its well-preserved city walls and tranquility. Originally a defensive outpost for Florence, the village now hosts the Castello di Volpaia winery. For nearly 900 years, almost every resident has been directly or indirectly involved in the production of wine and olive oil. Here, you can explore notable sites, including the deconsecrated Church of San Lorenzo and the Renaissance-style Commenda di Sant’Eufrosino.
Historic Vineyards & Wineries in Chianti
Castello di Verazzano near Strada in Chianti
Castello di Verrazzano, with over 1000 years of history, was originally an Etruscan and Roman settlement before becoming the birthplace of Giovanni da Verrazzano, the explorer of New York Bay. After passing through several influential families, it was restored by the Cappellini family, who revitalized its vineyards and historical charm. The castle offers various guided tours, from classic wine tastings to full gastronomic experiences, with options for lunch, dinner, and private tours.
Castello di Brolio near Radda in Chianti
Castello di Brolio, perched on a hill in southern Chianti Classico, has stood for over a thousand years and has been owned by the Ricasoli family since 1141. The castle, rebuilt in Gothic style by Bettino Ricasoli in the 1800s, features Renaissance gardens, English woods, and offers stunning views of the Chianti region and distant Siena. Visitors can explore the gardens, enjoy a wine tasting, and tour a small museum showcasing family artifacts (basic tour includes an hour-long garden visit and a wine tasting).
Castello di Albola near Gaiole in Chianti
Castello di Albola, stood atop of the Chianti hills, is a medieval village surrounded by picturesque vineyards. Since 1979, the Zonin family has revitalized the estate, enhancing both the vineyards and the manor house. In the charming wine shop in the medieval village, wine tourists and wine lovers alike can taste and buy wines, including particularly valuable vintages alongside olive oil.
Chianti Classico: The Black Rooster Tale
The Black Rooster is the iconic symbol of Chianti Classico wines, distinguishing them from other Chianti wines produced outside the Chianti Classico territory. This symbol dates back to the Middle Ages when the Lega del Chianti, a political and military institution of the Republic of Florence, used it to represent control over the Chianti area.
According to legend, the Black Rooster became the symbol after a unique competition was held to settle the border between Florence and Siena. Two knights were to ride from their cities at dawn, and the border would be set where they met. The Florentines, using a famished black rooster that crowed before dawn, gave their knight an early start, allowing him to meet the Sienese knight near Fonterutoli, just a few kilometers from Siena. This clever strategy led to the border favoring Florence, and since then, the Black Rooster became a lasting symbol of Chianti Classico.
More to Do Near the Chianti Region, Tuscany
🍇 Be Charmed by the Beautiful Gardens in Florence, Italy
🍇 Discover the Enchanting Small Towns of Southern Tuscany
🍇 Witness Renaissance Art at Florence’s Galleries & Museums
🍇 Experience San Miniato: Italy’s Graceful Hill Town & Truffle Haven
🍇 Marvel at the San Gimignano’s Medieval Streets & Towers
Where to Stay in the Chianti Region
If you’re looking to relax in Radda in Chianti, I highly recommend Palazzo Leopoldo Dimora Storica. The hotel has a historic vibe, but you’ll still enjoy modern comforts like air-conditioned rooms and a wellness center. It’s a great spot for exploring the Chianti vineyards and Siena, with restaurants and bars in town just a short walk away. They even have a cool underground-style pool, though I didn’t swim since it was chilly in November 🥶.
FAQ
What is the Chianti region in Italy known for?
The Chianti region is renowned for its world-famous wines, particularly Chianti Classico, which is produced according to strict regulations. The area is also known for its picturesque landscapes, medieval villages, and historic castles, many of which now function as wineries offering tastings and tours.
What towns should I visit in the Chianti region, Italy?
Key towns in the Chianti region include Greve in Chianti, known as the gateway to Chianti; Radda in Chianti, which was historically significant for its defensive walls; and Castellina in Chianti, famous for its Etruscan history and stunning views from its underground streets. Other noteworthy towns include Panzano, with its medieval atmosphere, and the tiny village of Montefioralle.
How do I get to the Chianti region from Florence?
The Chianti region is easily accessible from Florence, with the most popular route being the scenic SR222 road, known as the “Chiantigiana.” This road winds through vineyards, olive groves, and charming villages, making it a popular choice for visitors who want to experience the beauty of Tuscany.
Can I visit wineries in Chianti?
Yes, many wineries in Chianti welcome visitors for tours and tastings. Some of the most famous include Castello di Brolio, which is the oldest winery in the world, and Castello di Verrazzano, the birthplace of the explorer who discovered New York Bay. These wineries often offer more than just wine tastings, with options to explore the historic castles and estates.
What is the best time to visit the Chianti region, Italy?
The best time to visit Chianti is during the late spring (May to June) and early fall (September to October) when the weather is mild, and the vineyards are either blossoming or being harvested. These periods also avoid the peak summer crowds, allowing for a more relaxed experience.
Are there any wine festivals in the Chianti region?
Yes, Chianti hosts several wine festivals throughout the year, particularly during the harvest season in September. These festivals offer a chance to taste a variety of local wines, enjoy traditional Tuscan food, and participate in cultural events.
What are some outdoor activities to do in Chianti?
Apart from wine tasting, visitors can explore the region on foot or by bike, with many trails connecting the villages. Popular activities include walking tours through medieval towns, cycling between vineyards, and enjoying panoramic views from the hilltops.
Can I stay overnight in the Chianti region?
Absolutely. The Chianti region offers a range of accommodations, from luxury villas and historic castles to charming bed and breakfasts. Staying overnight allows visitors to fully immerse themselves in the Tuscan countryside and enjoy the tranquility of the region.
The Finale: Exploring Chianti, Italy’s Charming Wine Region
The Chianti region in Italy is a must-visit destination for both wine lovers and travelers. This part of Tuscany is dotted with vineyards that have been producing wine for centuries, with Chianti Classico as its flagship. Beyond wine, Chianti offers stunning scenery with rolling hills, cypress-lined roads, and medieval villages.
The region is also home to friendly locals who are happy to share their rich heritage. You’ll find the best of Tuscan cuisine here, from fresh pasta to hearty meats, perfectly paired with local wines. Greve, Castellina, and Radda in Chianti are parts of Tuscany you should not miss.