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Footpaths of Umbria - Walks, art & wine between Arezzo & Assisi

Six walks of between 5 and 7.5 km between Arezzo and Assisi through the inimitable Umbrian countryside.

Enjoy the art of Piero della Francesca, Luca Signorelli and Giotto.

Visit isolated hermitages, churches and cathedrals associated with St Francis.

Led by Dr Antonia Whitley, art historian and lecturer specialising in the Italian Renaissance.

07 - 14 May 2018 Fully booked

  • Assisi, St. Francis, by Frank Fox publ. 1915.
    Assisi, St. Francis, by Frank Fox publ. 1915.
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Listed in The Sunday Times' 100 Best Holidays of 2017

Umbria brings together art and architecture of the highest importance, unspoilt countryside of breath-taking beauty and pockets of rare tranquillity. Land-locked, and located more or less in the centre of the peninsula, the region is crisscrossed by ancient paths, used for millennia by myriad travellers, traders, pilgrims and preachers. Two itinerant denizens in particular are encountered time and again on this tour, St Francis of Assisi and Piero della Francesca.

Stimulated by the movement of people, goods and ideas along the Via Flaminia, the main route from Rome to Ravenna, the economic and artistic life of Umbria began to flourish in the Middle Ages. Ideas absorbed from Byzantium were encountered and transformed by stylistic novelties from Rome, Florence and Siena.

In the early thirteenth century, the son of a rich cloth merchant in Assisi, one Francis, came to prominence in the region; he shunned the material excess and increasing secularization around him and embraced humility, simplicity and harmony with nature as an alternative Christian approach. Perambulating throughout Umbria and central Italy he preached with fervour, touched the hearts of thousands and attracted devoted disciples. Out of this movement the Franciscan Order grew.

Building work on the Basilica di San Francesco began two years after Francis’s death in Assisi in 1226; the fresco cycles here are some of the most art historically important in Italy. Cimabue, Giotto, Cavallini, Pietro Lorenzetti and Simone Martini are all thought to have been involved in the work and, despite varying degrees of restoration and preservation, they constitute one of the great achievements of western civilization.

The early Renaissance painter Piero della Francesca is also associated with the region. Born c. 1412 in Sansepolcro, which lies just over the border in Tuscany, like all artists of his time he led a peripatetic existence, travelling wherever work took him. In many ways, he stands like a lone star, one who did not leave an obvious trail in terms of followers, but one so bright as still to shine today. Our Piero trail also includes The Resurrection, dubbed by Aldous Huxley ‘the best picture’, and the quiet power and subtle beauty of The Legend of the True Cross in Arezzo's Basilica di San Francesco.  

Day 1

Citta di Castello. Fly at c. 8.00am (British Airways) from London Heathrow to Bologna. Spend the first of four nights in Città di Castello.

Day 2

Montecasale, Sansepolcro. St Francis passed through the Convent of Montecasale in 1213 on his journey to the Adriatic and Jerusalem, and a small community of friars have continued to provide pilgrim accommodation since then. Walk Montecasale to La Montagna: 7.5 km, c. 2 hours. Ascent: 223m. Descent: 689m. A high-level walk on paths, tracks and exposed ground, and through woodland. Lunch in Sansepolcro, then visit the museum in the former town hall, where Piero della Francesca’s early masterpiece, Madonna della Misericordia and the marvellous Resurrection fresco are housed. (At the time of writing, the Resurrection fresco was only partially visible due to restoration work, but should be visible by 2018).

Day 3

Arezzo, Monterchi. Drive to Arezzo to see Piero della Francesca’s great fresco cycle, The Legend of the True Cross, painted for the Franciscan order and executed over a twenty-year period. After lunch walk from Monteautello to Monterchi: 5.5 km, c. 1 hour 30 minutes. Ascent: 235m. Descent: 350m. This is a gently undulating walk on farm tracks and country roads. Piero della Francesca’s beautiful Madonna del Parto has its own museum in the village.

Day 4

Le Celle, Cortona. Begin the morning’s walk from the immaculately kept Eremo Le Celle, which Francis visited in 1226. Walk from Eremo Le Celle to Cortona: 5 km, c. 2 hours. Ascent: 223m. Descent: 214m. Starting gently downhill, this walk begins on woodland tracks outside Cortona before joining a cobbled Roman path that leads uphill to the town centre. Cortona is highly attractive and has a good art gallery, notable for paintings by Fra Angelico and Signorelli.

Day 5

Collepino, Spello. Drive to Collepino, a restored mediaeval borgo with views of Monte Subasio and, on a fine day, the Monti Sibillini. Walk from Collepino to Spello, 6 km, c. 2 hours. Ascent: 316m. Descent: 602m. The route is downhill and on a level track to Spello, through olive groves running alongside the Roman aqueduct built to supply the ‘splendissima colonia Julia’. There is time to enjoy Spello’s harmonious architecture and the richly coloured Renaissance frescoes by Pinturicchio in the church of Sta. Maria Maggiore. First of three nights in Spello.

Day 6

Assisi. Morning walk from Pieve San Nicolò to Assisi: 6 km, c. 2 hours. Ascent: 281m. Descent: 462m. This is a walk on a strada bianca (rough farm track), minor roads and woodland paths. The path predominantly descends, although the last section is uphill through the Bosco Francescano. The walk ends through the city gate which leads directly to the Basilica. Here we see one of the greatest assemblages of mediaeval fresco painting, including the cycle of the Life of St Francis which some attribute to Giotto. There is time to walk through the austere mediaeval streets and visit the church of Sta. Chiara.

Day 7

Bevagna, Montefalco. Known as the ‘Balcony of Umbria’, Montefalco’s mediaeval church houses 15th-century frescoes of the Florentine and Umbrian school; the town is also well known for its inky and full-bodied Sagrantino wines. Walk on country trails and lanes from Montefalco to Fabbri: 5 km, c. 1 hour. Ascent: 321m. Descent: 364m. Drive to Bevagna, the Roman Mevania, home to one of Italy’s most harmonious squares.

Day 8

Drive to Rome with a break in Montegiove en route. Fly from Rome Fiumicino to Heathrow, arriving c. 8.30pm.

Image of Antonia Whitley

Dr Antonia Whitley

Art historian and lecturer specialising in the Italian Renaissance, though her interests also include paintings of World War One. She obtained her PhD from the Warburg Institute, University of London, on Sienese society in the 15th century and has published articles on related topics. She has lectured for the National Gallery and has taught in the War Studies department of King’s College, London. She organises adult education study sessions and has led many tours in Italy. Visit Dr Antonia Whitley's website.

Price – per person

Two sharing: £2,610 or £2,410 without flights. Single occupancy: £2,830 or £2,630 without flights.


Flights (Euro Traveller) with British Airways (Airbus A320/321); travel by private coach; hotel accommodation; breakfasts; 5 lunches and 4 dinners with wine, water, coffee; all admissions; all tips; all taxes; the services of the lecturer, tour manager and local guides where appropriate.


Hotel Tiferno, Città di Castello: a central, 4-star hotel, renovated respecting the original architecture. Hotel La Bastiglia, Spello: a well-appointed 4-star hotel at the apex of Spello, with wonderful views from the terrace.

How strenuous?

This tour should only be considered by those who are used to regular country walking, with some uphill content.  There are six moderate to strenuous walks of between 5 and 7.5 km. Strong knees and ankles are essential, as are a pair of well-worn hiking boots with good ankle support. If you are used to them you may find walking poles useful. Walks have been carefully selected but some steep paths are unavoidable (both uphill and downhill) and terrain can be loose underfoot, particularly in wet weather. Average distance by coach per day: c. 60 miles.

Are you fit enough to join the tour?

Group size

Between 10 and 18 participants.

Combining with Gastronomic Veneto, 16–23 May 2018

14 May: Finish in Rome with the Umbria group. Stay 2 nights in either Rome or Verona. The train between Rome and Milan takes about 3 hours on the fast train. Meet Veneto group at the hotel in Verona on 16 May (afternoon). You would need to book your accommodation in Rome – we suggest the Residenza di Ripetta or MRT can book two extra nights in Verona. You would need to book the train yourself.

Travel advice

Before booking, please refer to the FCO website to ensure you are happy with the travel advice for the destination(s) you are visiting:

Map for Footpaths of Umbria.

'The balance of activities was spot on. The food and wine was spectacular. The lecturer was outstanding. We were able to appreciate Italian art in a way we would have never achieved on our own.'

'We appreciated getting off the beaten track but we still thought we had a very good exposure to many of the highlights of Umbria.'

'I thoroughly enjoyed my holiday. For me, it offered everything I anticipated in the walking and art but, also, my fellow travellers were good company. I will certainly maintain contact with one or two of them who seemed to be kindred spirits.'

'The tour encompassed all my interests. The walks varied, the meals with the wine tastings were excellent and evenly paced, and the visits to view the art either before or after a walk were an absolute treat.'