Embark on a hiking adventure in Tuscany’s Chianti region, exploring ancient roads and reconnecting with the land’s rich history. Discover the beauty of the natural landscape and enjoy a delicious Tuscan lunch paired with wine.
Embark on a hiking adventure in Tuscany’s Chianti region, exploring ancient roads and reconnecting with the land’s rich history. Discover the beauty of the natural landscape and enjoy a delicious Tuscan lunch paired with wine.
- Castellina In Chianti - Castellina in Chianti is a comune (municipality) of c. 2,800 inhabitants in the province of Siena, in the Italian region Tuscany, located about 35 kilometres (22 mi) south of Florence and about 15 kilometres (9 mi) northwest of Siena. It is part of the Chianti Hills, between the valleys of the Arbia, Pesa and Elsa rivers….
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Castellina In Chianti - Castellina in Chianti is a comune (municipality) of c. 2,800 inhabitants in the province of Siena, in the Italian region Tuscany, located about 35 kilometres (22 mi) south of Florence and about 15 kilometres (9 mi) northwest of Siena. It is part of the Chianti Hills, between the valleys of the Arbia, Pesa and Elsa rivers.
The territory of Castellina in Chianti borders the following municipalities: Barberino Val d’Elsa, Castelnuovo Berardenga, Greve in Chianti, Monteriggioni, Poggibonsi, Radda in Chianti, Tavarnelle Val di Pesa.
The first settlements in the area dates from the Etruscan age, and they were probably devastated by Gaulish invasions at the time of the latter’s invasions against Rome.
In the early Middle Ages the town was known as Salingolpe; in the 11th century Matilda of Tuscany gave it as fief to the counts Guidi and, subsequently, to the Trebbio. In the early 15th century it became a stronghold, of which today the Rocca remain.

- Tour escort/host
- Wine tasting
- Lunch
- Alcoholic beverages
- Bottled water
- Tour escort/host
- Wine tasting
- Lunch
- Alcoholic beverages
- Bottled water
- Gratuities
- Hotel pickup & drop off
- Gratuities
- Hotel pickup & drop off
Chianti and its ancient roads offer a connection to the spiritual, archaeological, and rural traditions of the region. Few places in the world compare to Chianti, where the natural landscape seamlessly blends with centuries-old history. Numerous footpaths guide visitors along routes from the Middle Ages, leaving well-preserved traces in these hills….
Chianti and its ancient roads offer a connection to the spiritual, archaeological, and rural traditions of the region. Few places in the world compare to Chianti, where the natural landscape seamlessly blends with centuries-old history. Numerous footpaths guide visitors along routes from the Middle Ages, leaving well-preserved traces in these hills.
Accompanied by a local hiking guide, participants can explore these historic paths, once strategic routes that drew pilgrims to this magnificent area for centuries. This experience is an excellent way to appreciate Tuscany’s landscape in perfect harmony with nature. Simply take your time and immerse yourself in the surroundings.
Various hiking levels and routes are available, making this outdoor activity accessible to everyone. To enhance the experience, enjoy a traditional Tuscan lunch paired with wine.
The meeting point is at the office in Castellina in Chianti.
- Children must be accompanied by an adult
- Minimum drinking age is 18 years
- Dress code is smart casual
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.