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Cycling Through the Etruscan and Roman Heartlands of Umbria and Tuscany
Assisi-Perugia-Lake Trasimeno-Cortona-Chiusi-Città della Pieve-Orvieto-Todi
Embark on an evocative cycling tour through the timeless landscapes of Umbria and Tuscany, two of Italy’s most captivating regions. This journey takes you through the ancient heartlands of the Etruscan and Roman civilizations, along winding rivers, gentle hills, and valleys sculpted by both nature and centuries of human care. Every pedal stroke brings new discoveries: lush, fertile farmland, historic towns brimming with culture, and the unforgettable flavors of regional food and wine.
Your adventure begins in Assisi, the spiritual and artistic jewel of Umbria. This enchanting town—birthplace of St. Francis—invites you to wander its medieval streets, explore its peaceful monasteries and convents, and admire the stunning Basilica of St. Francis, home to world-renowned frescoes by Giotto and Cimabue. Here, devotion and art merge into an atmosphere that feels both sacred and timeless.
As you leave Assisi behind, your route unfolds through a landscape that seems perfectly balanced between humankind and nature. Rolling green hills dotted with olive groves and vineyards, crystal-clear rivers, and blue-shimmering lakes form the backdrop to your ride. Each town and village you pass—whether ORVIETO, Todi, Chiusi, Perugia, or Cortona—has its own unique charm and centuries of history to share. From Etruscan tombs and Roman ruins to medieval walls and Renaissance art, every stop tells another chapter of central Italy’s extraordinary story.
Along the way, you’ll also have the chance to indulge in the authentic cuisine of Umbria and Tuscany. Taste the region’s famed truffles, wild boar dishes, and handmade pasta, paired with exceptional local wines such as Sagrantino di Montefalco, Orvieto Classico, and Chianti Colli Senesi. In the evenings, relax in charming accommodations and enjoy slow, convivial dinners where every meal celebrates the connection between land, tradition, and people.
The 8-day tour can easily be extended by two nights, giving you more time to explore at a leisurely pace. The longer version includes extra nights in Città della Pieve, a delightful hilltop town known for its saffron and painter Pietro Vannucci (Perugino), and in Bevagna, a medieval gem where ancient Roman mosaics and artisan workshops reveal a vibrant cultural heritage.
By the end of this unforgettable cycling journey through Tuscany and Umbria, you’ll understand why these regions are often described as the soul of Italy—where art, history, landscape, food, and wine blend in perfect harmony.
The daily program of the 8-day tour
You arrive at your hotel in Assisi, a medieval town of global renown. The town is rich in both famous and lesser-known artistic treasures. Embraced within its old town walls on the slopes of Mount Subasio. Assisi is a magical place and the fact that it has hardly changed since ancient times has preserved its charm.
At the end of the afternoon drop off bicycles, if rented, bike fitting and route briefing. Overnight with breakfast in *** or **** star hotel near the old town centre.
Following quiet roads dominated by hills covered with vineyards and olive groves, you arrive at Ponte S. Giovanni, located at the foot of Perugia. Here you can visit the Ipogeo dei Volumni, which is an Etruscan tomb site discovered in 1840. From Ponte San Giovanni you can also visit the old town centre of Perugia by public transport. In just 15 minutes you are in the heart of Etrusca Perusia (Perugia) and you can appreciate the extraordinary Etruscan civilization by visiting the Etruscan Well (Pozzo Etrusco) as well as stopping to admire the old town walls and arches. Perugia is an eclectic and particularly beautiful city, which is rich in culture, architectural monuments, events, shops and characteristic wine bars where you can taste the famous Umbrian wines. Overnight stay in **** star hotel in Ponte San Giovanni.
Distance: 30,4 km / 18,9 mi; Ascent/Descent: +293m – 495m
To reach Passignano on the lake you cycle along roads, from which you enjoy a panorama of the rolling green hills. Passignano is located on the gently sloping northern shores, where the lake meets the rocks. The town is often referred to as ‘l’isola felice’ (“the happy island”) because it is a meeting place for nature and history, art and folklore, peace and vitality. Overnight stay in Passignano at a *** hotel or **** with pool and room with lake view.
Distance: 64 km / 39,7 mi; Ascent/Descent: +602m –540m
In the morning, you leave Passignano to head for Castiglione del Lago, a charming village at the western shore of Lake Trasimeno. Your journey through Tuscany begins here, in the farmlands of the Val di Chiana. Your route crosses a number of ‘food trails’ – cheese, fruit, olive oil, wine and Chianina beef – adding flavour to the list of attractions alongside history, art and water. Your Etruscan journey continues through legends and mysteries, ancient town walls and necropolis such as those of Cortona. This town is well worth exploring. Enjoy it in all its aspects. There is something of interest for everyone: art, food & wine and shops.
Castiglione del lago is built on a promontory and from the old centre, you have a nice view over the lake and its islands. Overnight stay in Castiglione del Lago in a *** hotel or a B&B the Charme
Distance: 51,1 km / 31,8 mi; Ascent/Descent: +548m –512m
The first part of this stretch offers you some wonderful atmospheric scenery. You pedal immersed in a green hilly landscape with glimpses of Trasimeno Lake and Chiusi Lake. You can decide to make a detour and visit Chiusi. Among the most interesting monuments to see in Chiusi we point out: the Cathedral, the Chiesa di San Francesco, the Bishop’s Palace, the Museo della Cattedra, the remains of the Fortress and Porsenna’s labyrinth. You then climb up to Città della Pieve, where are several important monuments from the 13th to 17th centuries. The town is the homeland of Perugino, the Maestro of Raphael. Pedalling along a route with rises and dips until you reach Orvieto, an ancient town rich in art and culture. It is certainly worthwhile to book an extra night in this lovely town to dedicate to its old town centre.
Your overnight stay is in the historical centre of Orvieto at a *** or **** star hotel
Route NOT passing Chiusi:
Distance: 69,8 km / 43,4 mi; Ascent/Descent: +1223m –1209m
Route passing Chiusi:
Distance: 72,6 km / 45,1 mi; Ascent/Descent: +1337m –1321m
Before leaving the splendid Umbrian town of Orvieto don’t forget to visit the Duomo, a masterpiece of Italian Gothic architecture. Its façade is decorated with magnificent bas-reliefs and sculptures designed by the Sienese architect Lorenzo Maitani. Also not to be missed are the Pozzo di San Patrizio, a great work of hydro engineering. In the saddle once more, you leave Orvieto to reach a panoramic road by Lake Corbara. Pedal slowly, enjoy all the shades of colour nature offers you and stop to breathe the fresh air. Today’s ride finishes in Todi, which in 1992 Prof. Richard S. Levine of U.S. Kentucky University defined as “the most livable town in the world”. Overnight stay in Todi at a *** or **** star hotel
Distance: 45,4 km / 28,2 mi; Ascent/Descent: +1014m –1035m
In the morning, you leave Todi and pedal through a hilly landscape of farmed fields and vineyards to get to Bevagna. This charming medieval village, listed as one of the most beautiful villages in Italy, is rich in art, history and cultural events that celebrate folklore and traditions (such as the ‘Mercato delle Gaite’). Leaving Bevagna you pass through lush, fertile land which belongs to the Sagrantino DOCG area. This is a wine with definite character and intense flavour, which is famous worldwide. You are now coming to the end of this evocative journey through the art, history and nature of the two unique and uncontaminated regions of Umbria and Tuscany. The last stretch of your trip brings you back to Assisi. Overnight stay in Assisi at a *** or **** star hotel
Distance: 54,7 km / 34 mi; Ascent/Descent: +1049m –951m
After breakfast ends your tour through the Umbrian & Tuscan lands.
The daily program of the 10-day tour
You arrive at your hotel in Assisi, a medieval town of global renown. The town is rich in both famous and lesser-known artistic treasures. Embraced within its old town walls on the slopes of Mount Subasio. Assisi is a magical place and the fact that it has hardly changed since ancient times has preserved its charm.
At the end of the afternoon drop off bicycles, if rented, bike fitting and route briefing. Overnight with breakfast in *** or **** star hotel near the old town centre.
Following quiet roads dominated by hills covered with vineyards and olive groves, you arrive at Ponte S. Giovanni, located at the foot of Perugia. Here you can visit the Ipogeo dei Volumni, which is an Etruscan tomb site discovered in 1840. From Ponte San Giovanni you can also visit the old town centre of Perugia by public transport. In just 15 minutes you are in the heart of Etrusca Perusia (Perugia) and you can appreciate the extraordinary Etruscan civilization by visiting the Etruscan Well (Pozzo Etrusco) as well as stopping to admire the old town walls and arches. Perugia is an eclectic and particularly beautiful city, which is rich in culture, architectural monuments, events, shops and characteristic wine bars where you can taste the famous Umbrian wines. Overnight stay in **** star hotel in Ponte San Giovanni.
Distance: 30,4 km / 18,9 mi; Ascent/Descent: +293m – 495m
To reach Passignano on the lake you cycle along roads, from which you enjoy a panorama of the rolling green hills. Passignano is located on the gently sloping northern shores, where the lake meets the rocks. The town is often referred to as ‘l’isola felice’ (“the happy island”) because it is a meeting place for nature and history, art and folklore, peace and vitality. Overnight stay in Passignano at a *** hotel or **** with pool and room with lake view.
Distance: 64 km / 39,7 mi; Ascent/Descent: +602m –540m
In the morning, you leave Passignano to head for Castiglione del Lago, a charming village at the western shore of Lake Trasimeno. Your journey through Tuscany begins here, in the farmlands of the Val di Chiana. Your route crosses a number of ‘food trails’ – cheese, fruit, olive oil, wine and Chianina beef – adding flavour to the list of attractions alongside history, art and water. Your Etruscan journey continues through legends and mysteries, ancient town walls and necropolis such as those of Cortona. This town is well worth exploring. Enjoy it in all its aspects. There is something of interest for everyone: art, food & wine and shops.
Castiglione del lago is built on a promontory and from the old centre, you have a nice view over the lake and its islands. Overnight stay in Castiglione del Lago in a *** hotel or a B&B the Charme
Distance: 51,1 km / 31,8 mi; Ascent/Descent: +548m –512m
Leaving Castiglione del Lago, you say goodbye to Lake Trasimeno. You cycle through a rural undulating landscape until the Etruscan town of Chiusi, which rises on a hill on the southern side of the Valdichiana. Between 7th and 5th century B. C. Chiusi got to its greatest splendour under the King Porsenna’s domination. Among the most interesting monuments to see in Chiusi we point out: the Cathedral, the Chiesa di San Francesco, the Bishop’s Palace, the Museo della Cattedra, the remains of the Fortress and Porsenna’s labyrinth. You then climb up to Città della Pieve, where are several important monuments from the 13th to 17th centuries. The town is the homeland of Perugino, the Maestro of Raphael. The city retains some of his most important works. Your overnight stay is in a **** star hotel
Distance: 30,4 km / 18,9 mi; Ascent/Descent: +625m –423m
You leave Città della Pieve and pedalling along a route with rises and dips until you reach first the small town of Fabbro and then Orvieto, an ancient town rich in art and culture. It is worthwhile to book an extra night in this lovely town. Interesting to visit is the Duomo, a masterpiece of Italian Gothic architecture. Its façade is decorated with magnificent bas-reliefs and sculptures designed by the Senesce architect Lorenzo Maitani. Also not to be missed are the Pozzo di San Patrizio, a great work of hydro engineering built by request of Pope Clement VII to ensure a water supply to the town in the case of a siege. He had taken refuge in Orvieto during the Sack of Rome in 1527.
Your overnight stay is in the historical centre of Orvieto at a *** or **** star hotel
Distance: 42,8 km / 26,6 mi; Ascent/Descent: +721m –913m
Before leaving the splendid Umbrian town of Orvieto don’t forget to visit the Duomo, a masterpiece of Italian Gothic architecture. Its façade is decorated with magnificent bas-reliefs and sculptures designed by the Sienese architect Lorenzo Maitani. Also not to be missed are the Pozzo di San Patrizio, a great work of hydro engineering. In the saddle once more, you leave Orvieto to reach a panoramic road by Lake Corbara. Pedal slowly, enjoy all the shades of colour nature offers you and stop to breathe the fresh air. Today’s ride finishes in Todi, which in 1992 Prof. Richard S. Levine of U.S. Kentucky University defined as “the most livable town in the world”. Overnight stay in Todi at a *** or **** star hotel
Distance: 45,4 km / 28,2 mi; Ascent/Descent: +1014m –1035m
Also today, you pedal through a hilly landscape of farmed fields and vineyards to get to Bevagna. This charming medieval village, listed as one of the most beautiful villages in Italy, is rich in art, history and cultural events, which celebrate folklore and traditions (such as the ‘Mercato delle Gaite’). You can see the remains of the Roman forum and of a Roman temple with half columns and pilasters. Not far from this is the site of the Roman baths, of which the frigidarium remains. The other buildings are of medieval and renaissance origin and demonstrate a perfect example of architectural harmony between the forces of municipal hegemony and ecclesiastical power. You will stay in the centre in a *** or **** star hotel
Distance: 33,1 km / 20,6 mi; Ascent/Descent: +735m –828m
Leaving Bevagna you go to Montefalco cycling through lush, fertile land which belongs to the Sagrantino DOCG area. This is a wine with definite character and intense flavour, which is famous worldwide. In addition, Montefalco is a hilltop town, called the balcony of the Valle Umbra, because of its stunning views over the valley. Then you descend into the valley and you pass Foligno, a lively town famous for its cosy restaurants and shopping streets. Your route takes you to Spello, another medieval town, which is well preserved, like Assisi. A panoramic road amongst olive groves will bring you back to Assisi, start point of this tour.
Distance: 36,7 km / 22,8 mi; Ascent/Descent: +563m –388m
After breakfast ends your tour through the Umbrian & Tuscan lands.
Impressions of Umbria and Tuscany
LEVEL 3,5
This tour is difficult! The 10-day tour is less strenuous because the longer stretches are divided into two. The tour is designed for those who like more challenging rides in rolling terrain with hills. You have to be trained and in good physical condition. Cycling is an important part of the day, but there will be still time left to explore the towns you pass through. There are significant differences in height. Not suitable for children under 14. ATTENTION also with E-bike you need to have a good cycling experience
Average daily distances:
8 day tour: 33 and 76 km / 20,5 and 47 miles.
10 day tour: 32 and 64 km
Total km:
316-323 km / 196-200 mi (8 days); 336 km / 209 mi (10 days)
DEPARTURES:
Daily from April until the end of October (excluded from 09/08-23/08/2026)
PARTICIPANTS:
2 or more people.
START / FINISH:
Assisi / Assisi
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