Trek Travel’s #6 Greatest Ride In The World.
Tuscany is one of the places to cycle that people dream of.
Discover this ride on our Tuscany Luxury trip.


Ribbons of road carving through the mountains and hillsides, mountain tops dotted with quaint villages, world reknown food, amazing wine, and Italian hospitality. Truly, what more could one want and desire.

Discover this ride on our Tuscany trip.

Today’s ride is a stunning loop from the village of Gaiole in Chianti heading out of the mountains and winding through the vineyards. Around 10km, the famed Castello di Brolio is just off our path. After passing the castle, the mountainous landscapes of Chianti give way to olive groves, vineyards, and gentle rolling roads snaking through the countryside. Around 30km into the ride, you will pass through Castelnuovo Berardenga, this is a great spot to refuel as you begin your ascent up Monteluco. The next 14.5km will take you to the top of today’s climb, which will average just over 3%. After ascending to the top, there is a little store to top up on water, and then you can enjoy the descent which will take you almost all the way back to our hotel.

“Another spectacular adventure! After an incredible trip to Napa with Trek Travel, we were excited to explore yet another amazing area with you. Tuscany was absolutely awesome, and we are already debating where we should go with Trek Travel next. Thanks for all that you do – we can’t imagine anyone doing it better.”
-Melissa, Trek Travel Guest

Three Things You Need to Know

The first 25km of today’s ride is mostly downhill, averaging -0.1%. And different points of the ride, on a clear day, Sienna is off in the distance less then 20km away.

Cycling in Chianti, the temperatures can be relatively cooler throughout the year, relative to those in Sienna. It is always wise to take layers with you, and prepare for the unexpected. Chianti seems to receive slightly more rain then some of the surrounding areas.

Great locations to refuel on the ride, 10.2km there is a cafe and the Enoteca of The Castello di Brolio. The next recommended stop for food and water is just before the 30km mark in Castelnuovo Berardenga. The final spot is on top of Monteluco at 44.2km.

Local Resources

The village of Radda in Chainti is just 11km away. For those looking to explore another quaint village with fantastic wines and restaurants, it is worth a stop. Bar Dante is a great place to sit and sip a drink, while meandering through the village you will find great cycling shops, and Enoteca’s.

If you have a desire to cycle the White Roads on a vintage bike, simply stop in to La Bottegga and talk to Emanuele Nepi (he is one of the owners). He will be able to help you find a vintage bike to rent, along with getting you in the vintage gear.

Siena is only 25km away, and it is well worth the trip. From exploring the Duomo di Siena, Tower of Mangia, and the Piazza del Campo are highly recommended. The La Bottega dei Sapori Antichi is a great spot to grab a sandwhich to go, while GROM – Il Gelato come una volta & Gelateria Kopakabana are our favorite spots for Gelato.

Discover this ride on our Tuscany trip.

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