A gravel bike adventure through the highlights of Tuscany and Umbria

Admiring the endless beauty of Umbria and Tuscany from the saddle of a gravel bike is a unique experience. In the itinerary below, we describe an 8-day trip from Assisi to Siena. This trip is offered by a local cycling tour specialist. Luggage transport, GPX routes, 24/7 support, and hotels are included. Read more about this at the bottom of the page. Of course, you can also plan this trip entirely on your own.

White Roads of Tuscany and Umbria

The route takes you along the most picturesque “strade bianche” in these two beautiful regions of central Italy. You’ll ride along bike paths and quiet country roads lined with olive groves, vineyards, and picturesque medieval villages.

Highlights of a gravel bike vacation in Tuscany and Umbria

• Assisi and Bevagna
• Umbria’s Most Famous Wine Region
• Strade bianche, the white gravel roads
• The Paths of St. Francis
• Foligno
• The Umbrian Valley
• Sagrantino
• Trasimeno Lake
• Solomeo
• Perugia
• Cortona
• Val d’Orcia
• Montepulciano
• Siena

Day 1: Arrival in Assisi

You’ll arrive in Assisi on your own. You’ll be welcomed by the organizers at the Santa Maria degli Angeli train station in Assisi and taken to your hotel. There, you’ll receive your bikes (if you’re renting them) and all the necessary information for your gravel adventure through Umbria and Tuscany. Take some time to explore Assisi; visit the sites associated with St. Francis and get ready for your first ride the next day.

Overnight stay in Assisi

Day 2: Gravel bike ride from Assisi to Spello and Bevagna

Distance: 65 km – Elevation: 600 m

The first gravel ride. From Assisi, you’ll reach Spello via the beautiful Via degli Olivi, at the foot of Mount Subasio. After Spello, you’ll continue on to Foligno and then to Bevagna, a beautiful medieval gem. The return trip to Assisi takes you through Piandarca, Cannara, and Rivotorto, home to the beautiful sanctuary.

Overnight stay in Assisi

Day 3: Cycling from Assisi to Perugia

Distance: 50 km – Elevation: 370 m

Today you’ll leave Assisi and cycle to Perugia. You’ll ride through lush southern countryside. You’ll pass through Bastia Umbra and follow the Chiascio River to reach first Costano and then Brufa.

From here, you’ll enjoy a beautiful view—mostly along strade bianche—down into the Tiber River valley. After crossing the river, you’ll ride past rolling hills near the outskirts of Perugia. Here, you’ll join the Trasimeno-Perugia bike path to reach the Pian di Massiano train station.

Here, you can hop on the mini-metro with your bike, which will take you to the heart of the Acropolis in about ten minutes. This way, you’ll avoid all the traffic and easily reach Perugia’s historic center and your hotel.

Overnight stay in Perugia

Day 4: Gravel ride from Perugia to Solomeo

Distance: 50 km – Elevation: 580 m

Today’s stage is quite challenging (at least the first 20 km) and takes you to the charming village of Solomeo, the home of cashmere. It has been lovingly restored by Brunello Cucinelli and his humanistic fashion company.

You’ll reach this beautiful spot by passing through the Monte Pacciano area north of Perugia. A sweeping view of Mount Tezio, Perugia’s “mountain,” and the surrounding countryside. From there, a series of beautiful, quiet strade bianche will lead you to Solomeo. It’s definitely worth stopping for a break! Afterward, continue on to your agriturismo, just one kilometer away.

Overnight stay in Solomeo

Day 5: Cycling from Solomeo to Cortona in Tuscany

Distance: 78 km – Elevation: 660 m

A long but mostly flat stage. It takes you along beautiful strade bianche with views of Lake Trasimeno. If you cycle around the lake from the south, you’ll arrive in the charming village of Castiglione del Lago, the perfect spot for a lunch break. After that, you’ll continue cycling into Tuscany.

Tip: Take it easy and save some energy for the end, because most of the elevation gain comes on the final climb to the beautiful town of Cortona.

Day 6: Gravel biking in Tuscany: from Cortona to Montepulciano

Distance: 59 km – Elevation: 690 m

This is your first stage entirely in Tuscany. From Cortona, you’ll cross the Val di Chiana via the most beautiful white roads until you reach the Abbazia di Farneta , one of the oldest Benedictine monasteries in the region, dating back to the 9th century AD.

After visiting the abbey, you’ll head down to the Chiana River and follow the Bonifica Trail until you reach Lake Montepulciano, a nature reserve known for its rich flora and fauna.

From here, a long climb toward Montepulciano begins; riding along strade bianche surrounded by vineyards and stunning views, you’ll reach the church of San Biagio and then your hotel.

Overnight stay in Montepulciano

Day 7: Gravel ride from Montepulciano to Buonconvento

Distance: 54 km – Elevation: 1,090 m

Today’s stage has the most elevation gain of the entire trip, but it also takes you through some of Tuscany’s most beautiful hilltop villages. You’re in the Val d’Orcia, one of the most beautiful valleys in Tuscany.

Tip: Start early so you can fully enjoy the scenery along the way:

• The first stop is the village of Monticchiello
• Then you’ll drive through the beautiful Renaissance town of Pienza, a terraced town perched above the Val d’Orcia and a filming location for iconic productions such as Ridley Scott’s *Gladiator*
• Next, Bagno Vignoni with the Piazza delle Sorgenti
• Then a steep climb of about 3 kilometers on to Vignoni Alto
• And then on to San Quirico d’Orcia with its beautiful Horti Leonini (Renaissance gardens)

You’ll end the day with a bike ride along one of the most beautiful strade bianche in the world—part of the permanent Eroica route—which will take you to your agriturismo near Buonconvento.

Overnight stay in Buonconvento

Day 8: Gravel bike ride from Buonconvento to Siena (Taverne d’Arbia)

Distance: 69 km – Elevation: 960 m

The final leg of this spectacular gravel bike tour. Today, you’ll spend most of your time on the world’s most beautiful strade bianche, with constant climbs and descents that will really put your legs to the test.

You’ll tackle the famous climb up Monte Sante Marie shortly after passing through Asciano, where the gradient can reach a steep 18%. But the breathtaking 360-degree view stretching from Monte Amiata to Chianti and the Crete Senesi makes it all worth it.

The stage ends in Taverne d’Arbia, where a member of the organizing committee will be waiting to drive you to Siena so you can avoid the busy suburbs.

Enjoy a day in Siena before continuing your trip.

Overnight stay in Siena

Day 9: The end of your gravel bike vacation through Umbria and Tuscany

Spend another day in Siena before continuing your trip. You can take the train or bus back to Assisi if you left your car there. You can also arrange a transfer (for a fee) through your tour operator.

This 8-day gravel bike tour starts in Assisi and ends in Siena. You’ll make your own way to Assisi—either by car or by flying from Rotterdam/The Hague Airport to Perugia with Transavia.

Gravel Bike Vacation in Umbria and Tuscany on a Map