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Footpaths of Umbria - Walks, art and wine between Arezzo and 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.  

Print itinerary (2024)

Print itinerary (2025)

16 - 23 Sep 2024 £3,260 Book this tour

  • Assisi, St. Francis, by Frank Fox publ. 1915.
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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 criss-crossed 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 13th 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 secularisation 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.

The video above was filmed on Footpaths of Umbria in June 2023.

Day 1

Città di Castello. Fly at c. 7.45am 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 from Montecasale to La Montagna: c. 7.5 km, c. 2 hours. A high-level walk on paths, tracks and exposed ground, and through woodland. It is graded as challenging given the uneven nature of the paths and a long downhill section at the end. 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.

Day 3

Le Celle, Cortona. Begin the morning’s walk from the immaculately kept Eremo Le Celle, which Francis visited in 1226: c. 5 km, c. 2 hours. This is a moderate walk that starts gently downhill, 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 4

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 20-year period. After lunch, walk from Monteautello to Monterchi: c. 5.5 km, c. 1½ hours. This is an easy, 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 5

Montefalco, Bevagna, Trevi. Known as the ‘Balcony of Umbria’, Montefalco’s medieval 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. An easy walk on country trails and lanes from Montefalco to Fabbri: c. 5 km, c. 1½ hours. Drive to Bevagna, the Roman Mevania, home to one of Italy’s most harmonious squares. First of three nights in Spoleto.

Day 6

Assisi. Morning walk from Pieve San Nicolò to Assisi: c. 6 km, c. 2 hours. This is a moderate 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 medieval fresco painting, including the cycle of the Life of St Francis which some attribute to Giotto. There is time to walk through the austere medieval streets and visit the church of Sta. Chiara.

Day 7

Collepino, Spello. Drive to Collepino, a restored medieval borgo with views of Monte Subasio and, on a fine day, the Monti Sibillini. Walk from Collepino to Spello: 6 km, c. 2 hours. This easy route is mostly 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.

Day 8

Spoleto. Spend the morning in Spoleto before driving to Rome. Fly from Rome Fiumicino to Heathrow, arriving c. 8.15pm

Nigel McGilchrist

Writer and lecturer who lived in Italy for over thirty years, latterly in Orvieto where he produced olive oil and wine. Worked for the Italian Ministry of Arts in the field of wall-painting conservation and has taught at Rome University, the University of Massachusetts and was Dean of European Studies for a consortium of American Universities. For six years he walked every path and village of the sixty inhabited Greek islands which culminated in the twenty volume McGilchrist’s Greek Islands, abbreviated to the Blue Guide to The Aegean Islands. He now lives on the island of Kythera.

Image of Thomas-Leo True

Dr Thomas-Leo True

Art historian specialising in Renaissance and Baroque architecture in Rome and the Papal States, and Assistant Director of the British School at Rome from September 2015. He received his doctorate from Cambridge University, and also studied at the British School at Rome, where he was Rome Scholar (2009–10) and Giles Worsley Fellow (2013). He has lived in Le Marche region of Italy and is currently writing his first book on the Marchigian Cardinals of Pope Sixtus V.

Price, per person


Two sharing: £3,260 or £2,960 without flights. Single occupancy: £3,570 or £3,270 without flights.


Two sharing: £3,330 or £3,110 without flights. Single occupancy: £3,710 or £3,490 without flights


Flights (Euro Traveller) with British Airways (Airbus 320); 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 walking guide. 


Hotel Tiferno, Città di Castello: central, 4-star hotel, renovated respecting the original architecture. Hotel San Luca, Spoleto: A comfortable 4-star hotel, located in an elegantly converted former tannery, just within the city walls. Single rooms are doubles for sole use throughout.


How strenuous?

This is a walking tour, graded moderate. There are six walks, three are easy, two are moderate and one challenging. It is essential for participants to have appropriate walking footwear, be in good physical condition and to be used to country walking with uphill and downhill content. If you are used to them you may find walking poles useful. Average distance by coach per day: c. 60 miles.

Are you fit enough to join the tour?

Group size

Between 10 and 18 participants.

Travel advice

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

Combine with

In 2024:

Gastronomic Basque Country, 2–9 September

Cave Art in Spain, 3–9 September

Sardinia, 6–12 September

The Etruscans, 9–14 September

Arts & Crafts in the Cotswolds, 24–28 September

The Cathedrals of England, 25 September–3 October

Bulgaria, 28 September–7 October

Belgian Modern Masters, 25–29 September

The Divine Office30 September–4 October


In May 2025: 

The Western Balkans, 12–25 May

Shostakovich in Leipzig, 14–20 May

Art in Scotland, 16–23 May

Arts & Crafts in the Lake District, 19–23 May

The Road to Santiago, 6–18 June

Traversing the Tyrol, 9–15 June

Eastern Turkey, 9–24 June

Moving on: Architecture & Memory, 10–16 June


In October 2025:

Bulgaria, 4–13 October

Habsburg Austria, 6–13 October

Ravenna & Urbino, 13–17 October

Siena & San Gimignano, 13–17 October

Palladian Villas, 28 October–2 November

The Western Balkans, 6–19 October

'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.'