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Medieval Umbria

Abbeys and Art in the Apennines

This tour begins with a leisurely olive oil tasting at an organic farm in the charming town of Anghiari before arriving in the historic market town of Sansepolcro, birthplace of the Renaissance artist Piero della Francesca.  Cross from Tuscany to Umbria in the Apennine mountains with beautiful views of both regions. Follow evocative pilgrim trails, once trodden by St Francis of Assisi, to remote churches and a dramatic fortress.  Walk along pretty woodland paths and enjoy an exclusive guided tour of a 13th century Benedictine monastery.  Stay in a beautifully restored Abbey and finish the holiday with three nights in the heart of the lovely town of Gubbio. 

The walking holiday starts and ends in Florence, the cradle of the Renaissance. There are daily flights from the UK and other European cities to Florence airport and the city is on a main train line from Milan and Rome. You can also request to join the tour in Arezzo which is on the train line from Rome.  For more ideas see our City Guides.

€2,625 per person
Single supplement:

Our tours are genuinely all-inclusive - learn more about what we offer. 

What's Included?

•    7 nights’ accommodation in 3 delightful hotels
•    Two experienced and knowledgeable guides who will look after your every need and bring this stunning area to life
•    All meals including wine
•    Gourmet picnic lunches each day and snacks en route
•    Dinner in a variety of superb restaurants
•    Museum visits and wine/food tastings as per itinerary
•    Support vehicle, enabling you to walk as little or as much of the trail as you please
•    Transport to/from Florence in air-conditioned minibus
•    Comprehensive pre-trip information
•    Luggage transported for you so all you need to carry is a small backpack

Tour Dates
27th May 2016 - 3rd June 2016

Day 1
Meet Florence Santa Maria Novella Train station at 11am. Drive (1½ hours) towards the charming town of Anghiari, where we start the tour with a leisurely lunch and an olive oil tasting at an organic farm.  We then continue the short distance to Sansepolcro. We stay for the next 2 nights in the heart of the town in the beautifully restored Renaissance palace Palazzo Magi.  This evening there is a guided visit to the town’s museum to see the renowned works by Piero della Francesca. After the visit we enjoy a glass of prosecco before dinner in a local restaurant.

Day 2
After breakfast stroll out of the hotel to experience the local market in the town before a short drive takes us to the evocative Franciscan convent and hermitage at Monte Casale. A beautiful hike follows a low ridge of the Alpi della Luna with views across the Tiber Valley. Picnic in the hills before returning to Sansepolcro. Time to explore the many churches and some of the lesser known sites of the town before dinner in a local restaurant. (6km/4miles)

Day 3
A short drive takes us across the border into Umbria. We start our walk high above the town of Citta di Castello and hike through open farmland and woods, passing abandoned stone houses and a dramatic fort before arriving at the stunning Abbazia San Faustino, a beautiful small hotel converted from a former abbey. Dinner in the hotel restaurant.  (16.5km/10.5miles)

Day 4
A leisurely walk in the remote farmland near the Abbey of San Faustino leads us to the historic cellars of a local winemaker. We visit their estate and taste their wines over a light lunch. Time to relax and enjoy the pool and the tranquil setting of Abbazia San Faustino in the afternoon. (10km/6miles)

Day 5
We depart San Faustino and a short drive takes us into the foothills of the Apennines from where we follow trails past hamlets and through woods to arrive at the Basilica of San Ubaldo, perched on a hill above the lovely medieval town of Gubbio. We walk down through the cobbled streets to arrive, on foot, at our delightful four star hotel in the heart of the town overlooking the square. We use this as our base for the final 3 nights of the holiday. Dinner in a local restaurant in Gubbio. (18km/11.3miles)  For more information on Gubbio see our Blog.

Day 6
A short drive takes us out of town for an exclusive guided tour of the thirteenth-century Benedictine abbey of Montelabate, formerly one of the most important abbeys in the region. Our picnic today includes wine, cheese and olive oil from the estate.  Later in the day we visit Gubbio's principal museum with the precious Iguvine Tablets from the 3rd century B.C.  This part of Umbria has important Etruscan heritage and bordered the lands of the Umbri tribes.  Dinner this evening is in the centre of Gubbio.
Day 7
Our final hike takes us to Monte Cucco National Park, a short distance from Gubbio. Starting from a high alpine meadow at 1132m we climb up through beautiful beech woods to emerge above the tree line at just above 1400m. We circle the summit of Monte Cucco, enjoying spectacular views across the Umbrian hills and to Le Marche towards the coast. We picnic in the alpine meadow before returning, by van, to Gubbio. Free time in the afternoon before our final dinner in a local restaurant. (6.7km/4.2miles)

Day 8
Return to Florence Santa Maria Novella station for 12pm and we will also drop off at Florence Airport, if required, by 1pm.

Extra Info


Shortest day: 6km/3.8miles
Longest day: 18km/11.3miles

There are 5 days of walking on the trip and one free day. We walk on strade bianche (gravel roads), on mountain trails, along woodland tracks and quiet tarmac roads. There are some long hiking days but there is always van support with the opportunity to walk a half-day. Most of this part of Umbria is one of rolling hills with some significant ups and downs. The walk on Day 7 is a rugged mountain trail with some exposed sections. Sturdy walking boots, with good ankle support, are recommended. Walking poles would be an advantage, especially on steeper sections.

We have compiled a Reading List for ideas for books to enjoy on your walking tour.

Walking Gear
For helpful hints on what to wear, visit our Kit List page.

Buying Wine
We are often asked where guests can buy back home the wines tasted on the tours.  Our wine page has a few helpful pointers.


Springtime is a delightful time to walk in central Italy. We are quite high up at times so can take advantage of the cooler temperatures for walking. Max 24° Min 18°. Rainfall 55mm.