Castellina in Chianti

what to see and do

(about 15 km from Castelvecchi, 20–25 minutes by car)

Castellina in Chianti is one of the most representative villages in the Chianti Senese area and an ideal half-day trip for those staying in Castelvecchi. The town lies along the ancient road connecting Florence and Siena and has preserved a strong medieval character, perfectly set within a landscape of rolling hills, vineyards, olive groves and woodlands.

The historic centre is compact and pleasant to explore on foot. One of the town’s landmarks is the medieval Rocca, which rises above the village. Inside the fortress is the Archaeological Museum of the Chianti Senese, housing Etruscan and Roman artefacts discovered in the surrounding area. Climbing to the top of the tower rewards visitors with panoramic views over the Chianti countryside, ideal for photography or simply for taking in the scenery.

A walk along the Via delle Volte is not to be missed. This ancient covered walkway runs beneath the medieval walls, connecting different levels of the village. The atmosphere here is intimate and authentic, with views of small craft shops, wine bars and quieter corners of Castellina away from the busiest streets.

Just outside the historic centre lies the Montecalvario Etruscan Tumulus, one of the most important archaeological sites in the area. Dating back to the 7th–6th centuries BC, it bears witness to the Etruscan presence in the Chianti region and offers an interesting insight for visitors wishing to explore the area’s ancient history beyond the medieval period.

Castellina in Chianti is also an excellent destination for wine lovers. Both in the village and in the surrounding countryside there are wine shops and wineries offering tastings of Chianti Classico and other local wines, often paired with typical products such as extra virgin olive oil, cured meats and Tuscan cheeses. Palazzo Squarcialupi, in the heart of the village, hosts a well-stocked wine shop where visitors can discover the many expressions of Chianti Classico.

The village is also home to several historic churches, including the Church of San Salvatore and the Pieve of Sant’Agnese, which reflect the architectural and religious development of the area over the centuries.

For guests staying in Castelvecchi, Castellina in Chianti is an easy and rewarding destination, perfect to combine with visits to other Chianti towns such as Radda or Gaiole. The visit can be enjoyed at a relaxed pace, alternating cultural sights, leisurely walks through the village and moments dedicated to food and wine, fully embracing the slow rhythm of the Tuscan countryside.