Umbria self guided walking holiday, Italy

Experience a self guided week of walking in rural Italy, away from the crowds, with luggage transfers, maps and trip notes adding to the authentic allure of ancient Umbria.
Montefalco Bevagna Cannara Spello Assisi
990To1900 excluding flights
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7 Days
Tailor made
More info
The price per person in double room includes 6 nights accommodation with breakfast, a visit of a farmhouse producing cheese and a wine and cheese tasting, transfers from and to the train station, luggage transfers and maps and roadbooks.
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Description of Umbria self guided walking holiday, Italy

This self guided walking holiday allows travellers to discover the green heart of Italy within the centrally located region of Umbria. This lesser-visited area is incredibly beautiful with small towns and villages scattered across a typically Italian landscape featuring olive groves and vineyards. Ancient cultural heritage abounds within authentic local products, among them the tastiest extra virgin olive oil in Italy (especially the one from Spello) and some of the noblest wines, including Sagrantino and Rosso di Montefalco, best enjoyed in at a wine cellar in Montefalco.

You’ll hike for around 10kms per day along unknown Etruscan paths and ancient Roman roads to medieval villages like Montefalco, Bevagna, Cannara, Spello and Assisi. Each village is like a jewel waiting to be discovered; places where you can enjoy freshly made food and wine and chat with local people. Walking through the narrow streets you can imagine that you are in ancient times and you will be able to easily appreciate the historic links between cultural heritage, cuisine and wine, and traditions that make Umbria a wonderful place from where to appreciate the Italian way of life.

In the small hillside town of Montefalco you’ll find “the balcony of Umbria” which is famed for its breathtaking panoramas. There is also the San Francesco museum, which features the Benozzo Gozzoli frescoes and one of the Nativities painted by il Perugino. Traditional lace and cloth work is on display throughout the town as are several cellars offering regional red and white wines.

In Bevagna you can visit the incredibly well preserved Roman and medieval buildings and enjoy local dishes in one of its small taverns. From Bevagna you can walk to Cannara, a little medieval town built on the banks of the river Topino. The name Cannara is derived from “canna,” meaning rushes, indicating that the land was once underwater.

Spello is another little jewel of a town that maintains all its features from the past. For the art lovers, Spello is well known for its wonderful frescoes by Pinturicchio which can be found in the 12th century church of S. Maria Maggiore. You will also find a couple of excellent enoteques (regional wine stockist) and two extra special restaurants.

Collepino is a very small village, the perfect place to pause for thought on a self guided walking holiday in Umbria. We suggest taking in the old aqueduct, the well preserved remains of the castle and the Romanic Abbazia.

Last, but not least, a visit to Assisi. You can reach it through two different paths: “sentiero degli olivi” (the olive groves path) or the Saint Francis’ path. Sightseeing in Assisi will no doubt consist of the Basilica di San Francesco, Giotto’s frescoes on the Upper Basilica, several chapels and the crypt in the Lower Basilica. Moreover, you can walk for an entire day admiring the Basilica di Santa Chiara, the Duomo di San Rufino, and walk uphill to the Eremo delle Carceri.

Umbria really is an excellent option for responsible travellers interested in self guided walking against an authentic rural backdrop, far from the crowds flocking to neighbouring Tuscany.

Price information

990To1900 excluding flights
Convert currency:
The price per person in double room includes 6 nights accommodation with breakfast, a visit of a farmhouse producing cheese and a wine and cheese tasting, transfers from and to the train station, luggage transfers and maps and roadbooks.
Make enquiry

Departure information

This trip can be tailor made throughout the year to suit your requirements

Travel guides

Italy walking
Passionate, food loving, fiery, elegant, religious and beautiful. These clichés about Italians pretty much fit the picture of walking holidays in Ital...
Atmosphere is everything in Umbria, and although Tuscany may have better marketing and more visitors, Umbria certainly matches it for untouched Etrusc...


20 Reviews of Umbria self guided walking holiday, Italy

4.5 out of 5 stars

Reviewed on 15 Oct 2019 by

The most memorable part of the holiday was the walking everyday and seeing new things was super. The small towns were great fun to explore. Read full review

Reviewed on 09 May 2019 by

The beautiful villages of Umbria were a delight. Read full review

Reviewed on 18 Mar 2019 by

It will certainly have benefitted local people, where we stayed and ate. The fact that we walked and did not use any vehicles except transfers from and to the railway stations at the start and finish. Read full review

Reviewed on 30 Oct 2018 by

The places we stayed were all wonderful! The choices of small hotels in the small towns were really terrific... Great walking opportunities everywhere in the small towns. People friendly and always willing to help if you need any advise. Read full review

Reviewed on 20 Jun 2018 by

Excellent, it was the first time we had been on a self-guided walking holiday and we were very impressed with the organisation, the bag pick-up, the routes and the chosen accommodation; they all had something different to offer. Read full review

Reviewed on 09 Jun 2018 by

It was excellent. The arrangements were exactly as described, directions for the walks were clear and accurate, and the locations where we stayed and walked were lovely. Read full review

Reviewed on 21 Apr 2018 by

The most memorable was meeting our host in Bevagna, the hotel was just exquisite and his company excellent. Excellent holiday, we were a small group of two couples who enjoyed the walking, the places we visited and immersing ourselves in all that Umbria could offer Read full review

Reviewed on 02 Oct 2018 by

It was a relaxing way to spend 6 days, just what we were looking for Read full review

Reviewed on 25 Sep 2018 by

Very enjoyable - well planned and detail information provided. Read full review

Reviewed on 11 Sep 2018 by

The walk from Spello to Assisi was lovely...The Basilica di St. Francesca in Assisi was a memorable and beautiful church, one of the most beautiful ever encountered in fact. Amazing frescoes and ceilings. Read full review

Reviewed on 07 Sep 2018 by

The Basilica in Assisi was breathtaking. I really enjoyed the Spello loop walk from Spello to Collepino and the walk from Spello to Assisi was wonderful. Spello is a beautiful little town and also Montefalco. The hotels were all excellent. Read full review

Reviewed on 18 May 2018 by

Walking along quiet lanes beside olive groves listening to Cuckoo's and nightingales. Seeing the walled towns in the distance and then getting the chance to explore them, visit museums and churches and eat really good food and drink local wines. Read full review

Reviewed on 19 Sep 2017 by

The most memorable bits might be the tasting dinner at Villa Colle di Rocco near Cannara, and visiting the lower church in San Francesco in Assisi at 8.15 am while mass was being sung in the chapel of St Francis's tomb and we only had to share it with three other people. Read full review

Reviewed on 10 Sep 2017 by

The beautiful towns in which we stayed, the walking and the passionate hoteliers and B&B people we met. So knowledgeable about Umbria's history, it's products (wine, cheese, figs, olives etc). Read full review

Reviewed on 13 Jul 2017 by

I very much enjoyed this holiday, and especially enjoyed visiting the various medieval towns, which all had their own character. The Umbrian countryside was green and gentle and a delight to walk through. I also enjoyed the accommodation, which again was varied, but each place very special. Read full review

Reviewed on 05 Oct 2016 by

We would have no hesitation in recommending this holiday and Umbria as a destination; it's full of history, wonderful scenery and people. Worth the star rating - excellent holiday. Read full review

Reviewed on 29 Jun 2016 by

And the team at the holiday providers made this journey SO EASY. Their preparation was PERFECT. And it was very easy to do business with them. They were absolutely delightful! I highly recommend them. Read full review

Reviewed on 08 Mar 2016 by

Wonderful! Umbria is a special place and we were happy to experience it in the off season. Read full review

Reviewed on 05 Oct 2015 by

It was fantastic. We would do it again in a heartbeat. Read full review

Reviewed on 24 Apr 2015 by

The most memorable part of this holiday was walking through the olive groves from Spello to Assisi which was amazing as was the Spello loop that took us up to a tiny village and then back around to Spello. Read full review

Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


1) We support a local NGO, TAMAT, that is working on a project to develop sustainable mobility (H2power project) and we buy their gadgets to fund their activities. They are working, with other partners, on developing a demonstrator vehicle that is using as fuel a variable mixture of methane and hydrogen, that can be produced from renewable energy sources. They also organize awareness raising events for citizens and students about sustainable development and mobility and about the solution to preserve our environment.
2) We support the set up of the Foundation “Archeologia Arborea” in Città di Castello, which aims are to support biodiversity, the identification and multiplication of varieties of fruit trees that are disappearing because not as productive as the modern ones, protection of the landscape, support to sustainable development. The Foundation will take care, develop, reproduce and spread the different varieties of old and typical fruit trees that is the heritage of the San Lorenzo Collection, that includes 400 trees (apple, pear, cherry, plum, fig, almond, quince and medlar trees) that have been found in Central Italy and reproduced to avoid their extinction.
3) The goal of the Umbria Region is to achieve the 65% of separate collection of rubbish in a few years. Some of the 92 Umbria municipalities have reached it yet. We help support Umbria environment giving to our clients information to support recycling explaining how to divide rubbish and where to throw it away. The most common categories of rubbish are: organic waste, non-recyclable waste and recyclable waste (paper, plastic, tin and glass). In the streets or in the hotels and B&B, you will find several containers that have different colours and have a label -written only in Italian- explaining what it must collect, so we provide our travellers with a simple guide with instructions to sustain recycling: check our little guide before disposing of your garbage to be eco-friendly!


1) We give to our clients a list of farmers’ markets: true open air food shops from the producer to the consumer, vegetables organically grown and “zero kilometers” far. Buying and tasting their products is a way to support small local producers that otherwise risk to disappear. Farmers’ markets in Umbria are part of a project called “ Campagna Amica” that identifies and safeguards Italian and certified farmers’ products. In these markets you can find women producing buffalo mozzarella and cheeses, farmers with fresh fruit and vegetables (there is also a cooperative that sells products grown in a jail by prisoners), producing and selling typical flours and beans and so on. We support all of them buying their products and organizing, when possible, tasting of their products.
2) We are associated to Le Mat - social entrepreneurs in tourism. This is their manifesto: " We would like a tourism able to open the minds towards those who are different from us, a tourism where you can meet people who are curious to meet you; where through travelling and discovering unfamiliar methods, thoughts and actions you can listen to thousands of stories and experiences of different cultures of local communities willing to exchange with and to welcome who come from abroad ...". We work with their franchisees, for example with an hostel located in the most beautiful square of one of the Medieval cities where the tour will bring you, that was once a convent of nuns. They promote meetings with local people living in the village, as Luciana, a woman that handweaves wool dyed only with vegetal colours from saffron and onion.

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