Day 1: Arrival in Assisi

You’ll be welcomed at the Santa Maria degli Angeli station in Assisi and transferred to your hotel. There, a member of our team will deliver your bikes and provide you with all the essential information for your adventure through Umbria and Tuscany. Take some time to explore the beautiful city of Assisi, visiting the sites of Saint Francis, and prepare for your first ride the next day.

Distance 65 km - 600 m. of elevation

Day 2: Assisi - Spello - Bevagna

Get ready for the first gravel ride of your journey. Starting from Assisi, you’ll reach Spello along the beautiful Olive Tree Path, set at the base of Mount Subasio. After Spello, you’ll continue to Foligno and then to Bevagna, a stunning medieval gem. The return route to Assisi takes you through Piandarca, the site of Saint Francis’s famous “Sermon to the Birds,” as well as Cannara and Rivotorto with its splendid sanctuary.

Distance 50 km - 370 m. of elevation

Day 3: Assisi - Perugia

Today, you’ll leave Assisi and head to Perugia, the capital of the Umbria region, riding through its lush southern countryside. You’ll pass Bastia Umbra, following the Chiascio stream to reach Costano and then Brufa. From here, a wonderful view will accompany you, mostly along white roads, down into the valley of the Tevere River. After crossing it, some gentle hills will take you to the outskirts of Perugia, where you’ll connect with the Trasimeno-Perugia bike path to arrive at Pian di Massiano. Here, you’ll board the MiniMetro with your bike, which will take you to the heart of the acropolis in about ten minutes, bypassing all traffic. You’re now in the historic center, where your hotel awaits.

Distance 50 km - 580 m. of elevation

Day 4: Perugia - Solomeo

Today’s stage is fairly challenging (at least for the first 20 km) and will lead you to the charming village of Solomeo, the village of cashmere and harmony, lovingly restored by Brunello Cucinelli and his humanistic enterprise. You’ll reach this heaven by passing through the Monte Pacciano area, north of Perugia, with sweeping views of Mount Tezio, Perugia’s “mountain,” and the surrounding countryside. A series of beautiful, quiet white roads will lead you towards Solomeo. Take some time to explore this enchanting village before continuing to the agriturismo, just one kilometer away, where you’ll spend the night.

Distance 78 km - 660 m. of elevation

Day 5: Solomeo - Cortona

This is a long but mostly smooth stage, taking you along beautiful white roads with views of Lake Trasimeno. Skirting the lake from the south, you’ll arrive at the charming village of Castiglione del Lago—an ideal spot for a lunch break. Take some time to relax here before continuing into Tuscany. Tip: pace yourself and save some energy for the end, as most of the elevation gain comes in the final climb to the splendid town of Cortona.

Distance 59 km - 690 m. of elevation

Day 6: Cortona - Montepulciano

This is your first fully Tuscan stage. Leaving Cortona, you’ll cross the Val di Chiana on beautiful white roads until you reach the Abbey of Farneta, one of the oldest Benedictine monasteries in the region, dating back to the 1st century AD. After visiting the Abbey, you’ll descend toward the Chiana River, following the Bonifica path until you arrive at Lake Montepulciano, a nature reserve known for its rich flora and fauna. From here, a long climb begins toward Montepulciano; riding on white roads surrounded by vineyards and stunning views, you’ll reach the Church of San Biagio and then your hotel.

Distance 54 km - 1090 m. of elevation

Day 7: Montepulciano - Buonconvento

Today’s stage has the highest elevation gain of the entire trip, but it will also take you through some of Tuscany's most beautiful hilltop villages. We recommend an early start so you can fully enjoy the wonders along the way! Your first stop will be the village of Monticchiello, followed by the stunning Renaissance town of Pienza, a terrace over the Val d'Orcia and a filming location for iconic productions like Ridley Scott’s Gladiator. Next, you’ll visit Bagno Vignoni and its Piazza delle Sorgenti, named after the large, historic rectangular pool at its center, fed by a natural hot spring that flows abundantly from the volcanic earth below. Now it’s time to tackle one of the steepest climbs of the trip—short (around 3 km) but with gradients often above 10%—leading you first to Vignoni Alto, then to San Quirico d’Orcia with its beautiful Horti Leonini, a well-preserved example of an Italian Renaissance garden. You’ll end the day riding along one of the world’s most beautiful strade bianche, part of the permanent Eroica route, which will bring you to your agriturismo near Buonconvento.

Distance 69 km - 960 m. of elevation

Day 8: Buonconvento - Siena (Taverne d'Arbia)

The final leg of this incredible gravel bike journey! Today, you’ll spend most of your time on the world’s most beautiful white roads, with continuous ups and downs that will truly test your legs. You'll tackle the famous climb of Monte Sante Marie shortly after passing Asciano, where the gradient can reach a steep 18%. The breathtaking 360° views from Monte Amiata to Chianti and the Crete Senesi will quickly make you forget the fatigue, filling your eyes and heart with wonder. The stage ends in Taverne d’Arbia, where a member of our staff will be waiting to take you by car to Siena, helping you avoid the bustling outskirts. Enjoy a free time in Siena before embarking on your next adventure.

Day 9: End of our service

Free time in Siena to visit the town before your departure for your next destination.