This moderate tour begins just north of Siena in a town called Monteriggioni. Before we visit this gem of a fortified medieval town, we'll first enjoy a ride in the famous woodlands and vineyards of the Chianti.

we begin with a short descent from Monteriggioni to then join a quiet unpaved road that climbs to Lornano. Following this panoramic road, descending and climbing, we'll pass lovely old stone houses surrounded by cypresses and vineyards. After riding through a small wood, the trail opens up to some stunning views as we climb higher and higher.

Fonterutoli, a tiny borough situated on the medieval "roman road" between Florence and Siena, will be a good spot to take a break. It is well-known for its excellent Chianti wine, as is Castellina in Chianti, which we'll reach at mid-day.

During the middle ages, Castellina was the head of the Chianti League, a military alliance against Siena that corresponds with today's Chianti Classico wine region. We'll have ample opportunity to taste and buy some of these wines in one of the many wine shops or while having lunch in the Antica Trattoria "La Torre", right next to the imposing medieval castle.

After lunch, there's time to wander through town, down the unique Via delle Volte, a street vaulted along almost its entire length.

The second half of the ride is mostly downhill, passing through woods, vineyards and the small town of Lilliano, with its typical tuscan "pieve", parish church of Santa Christina. In the 1700's Etruscan tombs were found here, dating from 500 A.C.E. From here, we can choose to end the ride with an easy descent along a paved road, or to stay off road and have a few more ups and downs, with a last short, steep climb to Monteriggioni.


Tour level : Moderate
Length : 25 miles (42 km)
Altitude gain : 2000 ft (650 meters)
Terrain : wide trails, dirt roads and paved roads

See Dates and Prices for more details
Contact us to reserve a tour

| Top of page |