Biking in Montepulciano – Tuscany

The region Tuscany is a land of cyclists, it offers a variety of itineraries. Biking is one of the best ways to explore more of this wonderful wine region!

Montepulciano is a scenic hilltop town. It stands on a limestone hill. This area is the right place for road and dirt road cycling routes, but good fitness is required.

The best period for cycling Tuscany on bike are from March to October. Riding in the summer can be hot, but you can bike early in the morning, avoiding the heat of the day. Many find it’s a great time to relax and plan their day.

If you are planning about cycling in Tuscany, the most important biking needs are a good bike (MTB or race), a helmet and a repair kit. Cycling with a helmet is really recommended!

Bike itineraries to Pienza

There are amazing bike routes from Montepulciano to Pienza. The trail types are mostly asphalt and dirt roads. You ride along the hills overlooking the amazing views of Val d’Orcia.

Most of the trails are suitable for advanced – experienced riders. They are quite challenging but definitely worth it!

1) Mountain bike route Montepulciano – Pienza

This is a gravel road and a road itinerary. Ideal for MTB, not for tour or racing bikes. You’ll bike through hills, valleys, olive groves and vineyards. This is a spectaculair itinerary for experienced mountainbikers.

Distance 27 km.

2) Road cycling route Montepulciano – Pienza

Explore this amazing cycle route to Pienza! The start and arrival point is Montepulciano. From here you start the bike tour among the hills of the Val di Chiana valley. Passing Montichiello you’ll see the very best of the iconic Val d’Orcia valley.

Panoramic roads lead you the Renaissance village Pienza. Once you’ve passed Pienza you take the road back to Montepulciano.

Distance 38 km.

3) Road cycling route Montepulciano – Acquaviva – Montepulciano Stazione

This itinerary is almost my daily bike exercise. It is a short ride from the historic centre of Montepulciano to Acquaviva, Valiano and Montepulciano Stazione.

Montepulciano, Acquaviva and Valiano are hilly villages. The biking route around Montepulciano Stazione is primarily flat.

After leaving Montepulciano this road passes the villages of Acquaviva and Valiano. Once you reach Valiano you turn back the way up to Montepulciano Stazione and Montepulciano.

In the countryside of Montepulciano you can see the hospital of Nottola.

Distance 27.6 km.

4) Road cycling route Montepulciano – Chianciano – Montallese – Montepulciano Stazione

It is a nice panoramic ride, it has not many up and downs. Starting in Montepulciano you follow the signs direction Chianciano and Chiusi.

Chiusi is the former Etruscan city in the province of Siena.

Along the road to Chiusi you pass my favorite pizza restaurant “Jamaica”. Jamaica is close to the discotheque La Bussola In. The pizza’s at Jamaica are huge and delicious!

Turning left you take the downhill road to Montallese. When arriving in Montallese turn right and you take the dirt road – cycle path to Lago di Montepulciano (Lake Montepulciano). This path is also called “Il sentiero della Bonifica.”

From there you follow the dirt road to Valiano, Montepulciano Stazione and then the road back to Montepulciano. Cycling uphill to Montepulciano is not easy. The road is not very steep but it is long. For this track you need a reasonable fitness.

Distance 53 km.

Happy cycling!