Top Chianti Historical Tours

Montalcino, the city center of the territory and important for one of the most famous wines of Italy: Brunello di Montalcino

The tour takes place in a historic company, among the first to be part of the Consorzio del Brunello di Montalcino, the company was founded in 1950 by Silvio Nardi, an Umbrian producer of agricultural machinery, who had fallen in love with the Tenuta di Casale del Bosco during his numerous visits to Montalcino. In 1958 the first bottle of Brunello under the Casale del Bosco brand was marketed, the company has maintained a long history of tradition over the years, demonstrated by the fact that for over 70 years the Nardi family has continued to manage everything. The villa is also a perfectly preserved witness to the past history of the area.

Discover three of Tuscany’s most beautiful towns as you explore Pienza, Montalcino, and Montepulciano in one day on this walking tour. With a private guide, see the splendid 16th-century Renaissance palaces of Montepulciano and walk through the town of Pienza, built by Pope Pius II. In Montalcino, take a guided tour of a winery and taste the renowned Brunello de Montalcino wine. Note: transportation is not included.

Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.

Ride through the rolling hills of Montalcino on a private e-bike experience for travelers seeking authenticity, exceptional wines, and a deeper connection with Tuscany.Set in the UNESCO-listed Val d’Orcia, the journey unfolds at a relaxed, immersive pace. Premium e-bikes ensure effortless riding, and scenic routes along the Via Francigena offer photo spots, storytelling, and local legends far from crowds. Discover hidden corners and panoramic vineyards on a private, immersive tour for lasting memories.Led by a certified guide, you explore the history, culture, and atmosphere of this region beyond a standard tour.The experience culminates with an exclusive winery visit, followed by a refined Tuscan lunch and curated wine pairing. Savor Brunello and Rosso di Montalcino, both organic certified, in a private, intimate setting. Designed for couples, families, and discerning travelers, this is an elevated, immersive way to discover Montalcino — private, seamless, far from ordinary tours.