In the morning of day two, after enjoying a breakfast buffet, we'll head out for our next adventure: riding our bike up to one of the most important towns in the Chianti, Castellina.

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. Olive groves in Chianti, TuscanyPerched high on a hill, the climb to Castellina is long yet gradual and we will be rewarded all along the way with breathtaking views of the famous Chianti vineyards.

Once in Castellina, we'll dine in one of our favorite Tuscan trattorias, La Torre, next to the medieval castle. We'll also walk along the Via delle Volte, a unique vaulted street.

After lunch, we will enjoy the mostly downhill terrain as well as a stop at a renowned winery.
A visit of the winery will be followed by a tasting of its excellent, award-winning wines. We'll then continue our journey, with a few ups and downs through the Chianti hills on our way back into the valley.

Back at the villa, there is time for some r & r or an optional cooking class before another scrumptious meal.



Tour level : Easy
Length : 29 miles (47 km)
Altitude gain : 1800 ft (600 m)
Terrain : Wide trails - dirt roads - paved roads

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Best of Chianti day 2