IL GIRO DEL BARONE

Sunday | 27km & 424m

Arriving mid-day Sunday, the Giro del Barone ride is just a short loop to stretch our legs and dial in our bikes. But already there will be plenty to see, for while this ride is only 27 kilometers in distance, it is clearly “Made in Chianti.” After all, we are in the heart of one of Italy’s most famous wine regions. Fittingly, we roll past Castello di Brolio early in the ride, just one of the many expansive domains tucked away in these rolling hills that will be on non-stop display throughout the week.

CASTELNUOVO BERARDENGA

MONTELUCO RADDA VIA VILA

Tuesday | 57km & 1,242m

The highlight of today’s ride is the spectacular climb to Monteluco. While there are numerous roads that climb to Monteluco, we start from Castagnoli, where the road climbs gently past the Cantalici Winery. The landscape and geography vary constantly over this 10-kilometer rise, while the descent offers spectacular views. 

We then roll through the sumptuous village of San Gusmè before riding over to Castel di Brolio, where we have our coffee stop at Café Agribar Brolio.
Brolio may be known for its wine, this café is a cycling hotspot, as it sponsors its own Eroica team and covers its walls with its rich collection of cycling memorabilia. While we are only a few kilometers from Lecchi, instead of returning directly, we loop around via Radda in Chianti. These are the roads of the annual Eroica vintage cycling event, and Gaiole in Chianti, home to the start and finish, is just a few kilometers up the road.

Volpaia COFFEE RIDE

Wednesday | 40km & 932m

Introduced this year on our Chianti Classico trip, the Volpaia loop has been an instant hit. Designed by inGamba guide Sancho da Cruz, it is one of his favorite rides. “Volpaia is even smaller than Lecchi,” says da Cruz. “But the first time I rode through the town, I just fell in love with it. It sits on top of this hill. The climb to Volpaia is not easy, but the views are simply amazing.”

In addition, the village itself is simply pristine, seemingly unchanged over the centuries, offering us the perfect spot for coffee. “As soon as I discovered this village, I knew I had to share it with the people at inGamba,” da Cruz adds.

Castellina

Thursday | 62km & 1,102m

The Castellina loop is one of our favorite Chianti Classico rides. The distance-to-climbing ratio is ideal, and each road offers stunning views. Early in the ride, we roll through Castellina itself, a picturesque and historic fortified town that dates back to the Etruscan period.

Riding south out of Castellina, views of Siena peak in and out of view on the horizon, dotted with lush vineyards. When it comes to sheer beauty, the Castellina loop is hard to beat, and it is obvious why it has been so popular over the years.

CRETE SENESI

Friday | 83km & 1,257m

For our final ride, we will do a short transfer out of Chianti into the Crete Senesi region. But while the Crete Senesi area borders Chianti, the landscape is distinctly different, as the familiar forests and vineyards of Chianti give way to more open terrain. It is here where much of the legendary Strade Bianche unfolds over rugged climbs like the Mont Santa Maria or the San Martin in Grania, which are so central to this contemporary classic.

It is our longest and most challenging ride, and the perfect ride to finish out an extraordinary week.

DEPARTURE

STAYING LONGER?

Adventure Continues…
Do you plan to come a few days early, or stay on after your inGamba adventure has ended? Our concierge can help you plan with a carefully curated selection of hotels, restaurants, bars, and guides. All of our recommendations have been hand-picked by a team of local experts, so you can spend more time enjoying all that this destination has to offer.