The Most Beautiful Chianti Villages to Visit in 2024

Staying at LA ROQQA, you can easily explore these beautiful towns and, after a day of discovery, return to the comfort and elegance of our hospitality, ready to relax and recharge for another adventure.

Here’s a guide to some of the most picturesque villages in the Chianti Valley, each offering a unique experience of Tuscany’s countryside.

Greve in Chianti

Known as the heart of Chianti, Greve is a charming village that serves as the perfect base for exploring the region and its centuries-old winemaking traditions. A highlight of any visit is the Wine Museum, where you can dive into the rich history and culture of Chianti wines. Don’t forget to stop by Piazza Giacomo Matteotti, a unique triangular square surrounded by restaurants and wine bars offering typical Tuscan products. 

Panzano in Chianti

Just a 10-minute drive from Greve, Panzano is a charming hilltop village offering stunning views of the Chianti countryside. With fewer than 1,000 residents, it’s rich in history, culture and authentic Tuscan charm. Among its highlights are the Panzano Castle, a medieval landmark, and the Church of Santa Maria, with its serene atmosphere and artistic details. For food enthusiasts, a stop at Dario Cecchini, the world-famous butcher, is an absolute must.

Radda in Chianti

Radda is a perfect destination for lovers of food and wine tourism. This picturesque village, recently renovated to restore its original charm, offers numerous opportunities to explore local wineries, renowned for producing fine wines – it is, in fact, considered the Capital of Chianti Classico. But Radda isn’t just for wine enthusiasts: strolling through its cobbled streets, discovering romantic corners and scenic views, you can visit the Palazzo del Podestà and the Church of San Niccolò.

Castellina in Chianti

Castellina in Chianti offers the perfect fusion of history and nature. The village is best known for its rampart walk, an elevated pathway hidden behind the battlements of an ancient castle, offering spectacular panoramic views of the rolling Tuscan hills. History enthusiasts can visit the Etruscan Tomb of Monte Calvario, while the charming alleys of the historic center, filled with traditional shops and cozy taverns, are perfect for a leisurely stroll.

Volpaia

Step back in time in Volpaia, a small fortified village known for its stone architecture and exceptional organic wines. As you wander through its ancient walls, you’ll experience an authentic and tranquil atmosphere, far from mass tourism. Key spots include the Church of San Lorenzo and the Ospedaletto dei Cavalieri di Malta, which once cared for pilgrims in the 1400s.

Gaiole in Chianti

Gaiole is the gateway to the Strada dei Castelli, a scenic route perfect for hiking and leisurely walks. Explore historical castles like Cacchiano, Brolio, Meleto, Vertine, San Polo in Rosso, and Castello di Ama. Within the village, don’t miss the Church of San Sigismondo, Piazza Ricasoli, the vibrant heart of the village, and the Pieve di Santa Maria a Spaltenna,  a medieval church in a rural setting.

Montefioralle

Montefioralle, one of Italy’s smallest and most enchanting villages, attracts visitors with its narrow alleys, charming stone houses, and streets adorned with flowers. It’s an ideal spot for a romantic walk and to soak in the authentic atmosphere of the Tuscan countryside.

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