Tuscany and Umbria: Cycling in the Heart of Italy

Day 1: Arrival

On the first day you arrive in Assisi, a medieval town of global renown which 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. You cannot miss the opportunity to admire the Basilica of St. Francis, an architectural masterpiece which consists of two churches, one above the other, and is brimming with frescos by great masters such as Giotto, Cimabue and Simone Martini.

To fully appreciate this historical town, however, it is also worth visiting historical sites dating back to the Roman period, such as the Roman Forum with its archaeological remains and the Temple of Minerva. Wander the narrow streets and allow yourself to be enchanted by the beauty of all the town's buildings, both sacred and secular. At the end of the day: route briefing and bike setting.
Overnight in Assisi

Day 2: Assisi – Ponte San Giovanni
19 miles/31 km

Following the paths and roads of a part of the 'Valle Umbra' valley, dominated by hills thick with vineyards and olive groves, you arrive at Ponte S. Giovanni. Here you can visit the Ipogeo dei Volumni, which is an Etruscan tomb site discovered in 1840 and now classified as one of the most important monuments of the Etruscan period. This site, along with many other findings, is part of the Palazzone Archaeological Park.

From Ponte San Giovanni you can also visit Perugia, taking the train for Sant'Anna station. In just a few 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) and the necropolis in the suburbs as well as stopping to admire the old town walls and arches. Perugia is an eclectic and particularly beautiful city, rich in culture, architectural monuments, events, shops and characteristic wine bars where you can taste the famous Umbrian wines.
Overnight in Ponte San Giovanni

Day 3: Ponte San Giovanni – Passignano
40 miles/64 km

To reach Passignano you cycle along paths and roads which enjoy a panorama of the rolling green hills sloping down to the shores of Lake Trasimeno. Passignano is 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.

It was along these north shores, between Malpasso and Passignano, that the epic battle between the Carthaginians and the Romans took place; the battle which marked the beginning of the legendary 20-year war between Hannibal and the Romans.
Overnight in Passignano

Day 4: Passignano – Cortona – Castiglione del Lago
32 miles/51 km

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, with the fragrance of its orchards.

Your route, in fact, crosses a number of 'food trails' - cheese, fruit, olive oil, wine and Chianina beef - adding flavor to the list of attractions alongside history, art, human resourcefulness and water. Your Etruscan journey continues through legends and mysteries, ancient town walls and necropolis such as those of Cortona. This town is an important cultural and artistic center for the valley, well worth exploring and enjoying in all of its aspects, and something of interest can be found here for everyone: enthusiasts of history and art, lovers of nature and adventure, those keen on sport and fitness, food and wine experts and those interested in fashion and shopping.

Castiglione del Lago is built on a promontory and from the old center; you have a nice view over the lake and its islands. Evidence can be found in the town of both Etruscan and Roman origins and there is the 6th century castle Rocca Leone, built by Emperor Frederick II. The town is a real meeting place for nature and history, art and folklore, peace and vitality. From Castiglione del Lago you can visit Isola Maggiore, one of the three islands in Lago Trasimeno. It has less than 100 permanent residents who live in homes dating back to the 15th century.
Overnight in Castiglione del Lago

Day 5: Castiglione del Lago – Orvieto
43 miles/70 km OR 45 miles/73 km with detour to Chiusi

The first part of this stretch offers you some wonderful atmospheric scenery. You pedal immersed in the green landscape slight hilly landscape of the surrounding areas of Lake Trasimeno and will have a glimpse of Lago di Chiusi.

You can decide to make a detour and visit 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 splendor under 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. Pedaling along a route with short rises and dips until you reach Orvieto, an ancient town rich in art and culture. It is worthwhile to book an extra night in this lovely town.
Overnight in Orvieto

Day 6: Orvieto – Todi
28 miles/45 km

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 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.

In the saddle once more, you leave Orvieto to reach a panoramic road by Lake Corbara. Pedal slowly, enjoy all the shades of color nature offers you and stop to breathe the fresh air. If you are a keen historian remember that near here, where the Paglia and Tiber rivers meet, are the remains of what was an important river port in Roman times (The Roman Port of Pagliano).

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”. Todi is another Etruscan town, but was founded between the 8th and 7th centuries BCE by the Umbri (whose settlements were on the other side of the Tiber from the Etruscans) and named Tutere, which means 'boundary town'. In 340 BCE the town developed significantly when it was conquered by the Romans. It acquired the name Colonia Julia Fida Tuder (1st century BCE) and was granted the right to mint its own currency. The town's most beautiful Roman constructions were built after it became part of the Roman Clustumina tribe.
Overnight in Todi.

Day 7: Todi – Bevagna – Cannara – Assisi
34 miles/55 km

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 which celebrate folklore and traditions (such as the 'Mercato delle Gaite'). If you visit the village starting from the upper part you find some important Roman monuments dating back to the 1st -2nd century C.E.

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. This is decorated with a very fine mosaic in black and white tiles with designs inspired by the sea. Walking along the narrow streets you come across the Roman theatre, of which evident and significant signs are still visible and which determines the curve of the houses built on the remains of this great civilization. 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.

Leaving Bevagna you pass through lush, fertile land which belongs to the Sagrantino DOCG area. This is a wine with definite character and intense flavor, which is famous worldwide. Your route takes you to Cannara, which rises on the left bank of the Topino river and is situated almost at the center of the Valle Umbra in an area which in ancient times was wetland (known to the Romans as Lacus Umber). Cannara, in fact, derives its name from 'canna' (cane), an aquatic plant which still thrives today. Historians reckon that the first settlements in this marshy area were founded in around 1000 C.E.

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 to Assisi.

Embraced within its old town walls, Assisi is a serene and atmospheric town which is a symbol of peace and harmony. It is a place of saints, churches, monasteries, and convents; buildings in which devotion and art live together in a symbiosis which few places have ever equaled. A grand example of this is the Basilica of St. Francis.

Nevertheless, in Assisi the secular buildings in the town also blend in perfectly with the religious architecture. Crossing the main square, Piazza del Comune, you can admire secular medieval buildings such as the Palazzo del Capitano del Popolo along with the Roman temple of Minerva, which has now become the Church of Saint Mary above Minerva. At the end of the town square, if you go into the Museo del Foro Romano, you are effectively turning back to pass under the present-day square. In the vaults here you can admire the original paving and the remains of impressive masonry and sculptures. The magic of this town can also be felt in the evening, sipping a glass of wine in one of the characteristic local wine bars, or at night when you wander the tastefully lit streets and alleys.
Overnight in Assisi.

Day 8: Departure from Assisi