Podere Castello 14

San Polo in Rosso is the fortified church you can see from Podere Castello. This remarkable Romanesque parish church dates to the 11th-12th century and was converted into a fortress during the 13th-14th century when it sat on the contested border between Florence and Siena. The church, rectory, courtyard, and even the bell tower were all fortified. Inside the three-nave basilica are 14th-century frescoes in the style of Ambrogio Lorenzetti (dated 1367) portraying the life of Christ. The church is now part of a private estate and is occasionally used for weddings and summer concerts. It's one of the most picturesque examples of a fortified church in Chianti.

Castello di Brolio is nearby and worth visiting for wine enthusiasts. This is where Baron Bettino Ricasoli created the modern Chianti Classico formula in 1872, defining the blend of Sangiovese, Canaiolo, and Malvasia that became the standard for the region. The Ricasoli family has held Brolio since 1141, making it Italy's oldest winery. Today you can tour the formal gardens, visit the museum dedicated to the "Iron Baron" (who was Italy's second Prime Minister during the Risorgimento), and taste the estate's wines at the on-site osteria. The castle itself is a striking neo-Gothic structure perched on a hilltop with panoramic views - though the fortifications date to the 11th century, what you see today was rebuilt by Baron Bettino in the 1800s.

Castello di Meleto (2 miles south) is probably even older than Brolio, built in the 12th century and considered virtually impregnable until an Aragonese army stormed it in 1478. The castle features circular towers characteristic of medieval Chianti defenses. Today it's a winery and farm estate producing Chianti Classico, olive oil, and cured pork from Cinta Senese pigs (a prized local breed). Daily tours include the ancient cellars.

Gaiole in Chianti (nearby) is a market town in the heart of Chianti Classico country. It developed in the 13th century as a trading place and became one of the three capitals of the Chianti League (alongside Radda and Castellina) - a political and military organization that controlled this territory under Florentine rule for over four centuries. The main street, Via Ricasoli, is pedestrianized with pleasant cafes and wine bars. Forbes named Gaiole number one in its list of "Europe's Most Idyllic Places To Live."

Other fortified churches and castles in the area include the Priory of Santa Maria a Spaltenna (another fortified Romanesque church), the fortified village of Vertine (mentioned in 11th-century records from Coltibuono Abbey), and Castello di Barbischio. This area was the frontline between Florence and Siena for centuries, which is why there's a fortress or fortified church on practically every hilltop. The so-called "Strada dei Castelli di Chianti" (Chianti Castle Road) links many of them.

Siena is 20km away (about 30 minutes by car). The Campo, the Duomo, the Palio horse race in July and August, and the warren of medieval streets make this one of Tuscany's essential stops. If you're visiting during the Palio, book restaurants well in advance.

[Florence]((/guide/italy/tuscany/florence) is about an hour by car (60-65km). The Uffizi, the Duomo, the markets of San Lorenzo, and the views from Piazzale Michelangelo are all within reach for a day trip. Parking can be challenging - consider the Park & Ride lots outside the center and taking the bus in.

Radda in Chianti (about 15-20 mins) is another classic Chianti town, historically one of the three "terzieri" (districts) of the Chianti League. The circular medieval center, the Palazzo del Podestà with its coats of arms and elegant arches (former headquarters of the Chianti League for four centuries), and the views from the town walls make it worth a visit.

Badia a Coltibuono (3 miles north of Gaiole) is a deconsecrated Benedictine abbey with a Romanesque church that now oversees production of excellent Chianti Classico. It's famous for its cooking school founded by Lorenza De' Medici, and the evocative remains of the fortress of Montegrossi are nearby.

Wine tours and tastings are everywhere in this part of Chianti Classico. Beyond Brolio and Meleto, estates worth visiting include Castello di Ama (where centuries-old winemaking meets contemporary art installations), Castello di Volpaia (a fortified village that's now a winery), and the numerous family-run vineyards along the back roads. Ask us for recommendations based on your interests - some specialize in tours and tastings, others are more low-key farm visits.