Castelvecchi – Wine, History and Cycling Routes in Chianti

Castelvecchi combines the tranquil landscape of Chianti with an unusually tangible history. The small hamlet lies in the hills above Radda in Chianti at an altitude of 600 metres, surrounded by vineyards and oak forests. At the same time, several circular cycling routes start here, connecting villages, parish churches, wineries and the region’s characteristic white roads. Depending on your interests, Castelvecchi can therefore be explored as a starting point for culture, wine and active days.

Wine landscape between vineyards and oak forests

The Castelvecchi estate encompasses around 300 hectares of vineyards and forests in the heart of Chianti. The Castelvecchi vineyard lies northwest of the municipality of Radda in Chianti at 530 metres above sea level; its soils consist of galestro and sandstone. Castelvecchi is also home to the Madonnino vineyard, located in front of the Pieve di Santa Maria Novella. It is one of the oldest vineyards in Chianti. For centuries, Fattoria Castelvecchi has produced wines, extra virgin olive oil and grappa on its estate of around 300 hectares. During a wine tasting, biological Chianti Classico wines, produced exclusively for the guests of the Borgo, are paired with a Tuscan platter of cold cuts and cheeses that can be adapted to taste. The place is therefore not only a landscape, but also a cultural setting closely connected with regional products.

Medieval traces in today’s hamlet

The origins of Castelvecchi date back to the 10th or 11th century. In medieval records, the place was referred to as “Castello et Curtis”. This designation indicates a military function and the presence of a manor. Historically, Castelvecchi served for observation and defence and was fortified with strong surrounding walls. This past is particularly vivid in the historic cellars. They encompass around 1,000 square metres of underground rooms and were built on the foundations of a medieval defensive complex. Those wishing to combine wine and history will therefore find not two separate themes here, but their spatial connection within the same place.

Four circular cycling routes with different distances

The circular cycling route “Il giro delle pievi” starts and ends in Castelvecchi, passes through Volpaia and the Pieve di Santa Maria Novella, is around 30 kilometres long and runs mostly along white roads. A longer option is “Il classico raddese”: it also starts and ends in Castelvecchi and passes through Radda in Chianti, Panzano in Chianti and Greve in Chianti. It is approximately 65 kilometres long. The challenging circular cycling route “Le strade bianche di L’Eroica” leads from Castelvecchi via Gaiole in Chianti, Brolio and Castelnuovo Berardenga back to the starting point. It is approximately 80 kilometres long and partly follows the L’Eroica route. Shorter than this tour, but longer than “Il giro delle pievi”, the moderately challenging “L’anello delle cantine” route starts in Castelvecchi, passes through Monterinaldi, San Sano and Ama before returning to Castelvecchi, is approximately 40 kilometres long and combines cycling with the discovery of Chianti Classico wineries.

Getting your bearings around Castelvecchi

Castelvecchi is approximately 3 kilometres from Radda in Chianti. A large car park is available near the Pieve. This information complements the cycling routes and historic sights with a specific point of reference for exploring the area. For further options within the same broader destination area, you will also find Lucarelli and Castello Di Volpaia.

For the overview of the broader destination: Radda / Chianti.