Medieval Umbria

Abbeys and Art in the Apennines

This tour starts in Arezzo with a visit to the world-famous fresco cycle by Renaissance artist Piero della Francesca before continuing to a leisurely lunch and olive oil tasting at an organic farm in the charming town of Anghiari.  We stay in the historic town of Sansepolcro and cross from Tuscany into Umbria over the Apennine mountains with beautiful views across both regions. We follow evocative pilgrim trails, once trodden by St Francis of Assisi, to remote churches, a dramatic fortress and a 13th century Benedictine monastery. We sleep in a beautifully restored abbey and finish the holiday with three nights in the heart of the fascinating town of Gubbio, with its Etruscan, Roman and medieval history. The final day of our tour coincides with the unique medieval crossbow festival for which Gubbio is famous, and we have the rare chance to witness this stunning spectacle. To find out more see our Blog on Il Palio della Balestra.  

The walking holiday starts and ends in Arezzo which is on the train line from both Florence and Rome. The journey time from Florence is approximately 1.5 hours and from Rome 2.5 hours and both have regular services. Our meeting point is the Hotel Continentale, which is very close to the train station, and we return guests to Arezzo station at the end of the tour. For more ideas on visiting these areas see our City Guides.    

"I spent over 20 years as a business consultant helping large and small clients perform better but I didn’t come across many small businesses as well run as yours. All the hotels, meals and wine were first class – some special indeed – which tells me that we, on the receiving end, have benefited from your insightful and extensive research. Bravo Zulu!"  Gordon Ramsay

As we are a small company and lead our tours personally, it is not possible to schedule all itineraries every year. The next departure for this tour is planned for 2024.

Cost: €3,050 per person

Single supplement: €350

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 to 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 Arezzo in air-conditioned minibus
  • Comprehensive pre-trip information
  • Luggage transported for you so all you need to carry is a small backpack

Your Health and Safety

See our new protocols to ensure the safety and wellbeing of both our guests and HH staff.

Tour Highlights

  • Outstanding hiking in lesser-known corners of Tuscany and Umbria
  • Lunch at an organic olive oil farm
  • See world-famous Piero della Francesca paintings


Terrain: Hilly terrain, most walking on dirt roads and woodland tracks. Challenging (optional) final walk on mountain trails

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

We have graded this hike a Level 3. Some of our tours are more challenging than others, so see how we grade our hikes to make sure you choose the right one for you. If you are interested in this tour, then you might also like to take a look at Etruscan Trails in Central Italy, Parma Tuscany and the Ligurian Sea,  Northern Tuscany and Ravenna or Lucca, Volterra and the Island of Elba



Palazzo Magi: 4-star Renaissance palace in centre of Sansepolcro

Abbazia San Faustino: Luxurious country hotel with swimming pool converted from a 13th century abbey

Relais Ducale: 4-star hotel in heart of Gubbio. Formerly the Ducal Palace

Tour Dates

20 - 27 May 2024