Medieval Umbria
Abbeys and Art in the Apennines
Tour Dates
19 – 26 May 2025
Tour Cost
€3,195 per person
Single supplement: €325
This tour starts in Arezzo with visits to world-famous paintings by Renaissance artist Piero della Francesca, before continuing to a leisurely lunch and olive oil tasting at an organic farm. We stay in the charming town of Anghiari, explore nearby Sansepolcro, and cross from Tuscany into Umbria over the Apennines 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, known as Il Palio della Balestra, and we have a 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.
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
Our tours are genuinely all-inclusive – learn more about what we offer.
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
Walking/Terrain
Terrain: Hilly terrain, most walking on dirt roads and woodland tracks. Challenging (optional) final walk on mountain trails
Shortest/Longest Day: 6km/3.8miles:19.5km/12 miles
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
Accommodation
Hotel La Meridiana: a friendly family-run hotel in the heart of Anghiari
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
Itinerary
LEAVE BLANK
Day 1
We meet in Arezzo at 08:45 at the Hotel Continentale, situated on Piazza Guido Monaco, very close to the train station. We start with a guided visit to the San Francesco church to see the world-famous fresco cycle by Piero della Francesca, known as “The Legend of the True Cross”. A short drive takes us out of Arezzo to the village of Monterchi, home to another of Piero’s masterpieces, “The Madonna del Parto”. After visiting this museum, we drive to an organic farm for a leisurely lunch and olive oil tasting. In the afternoon, we check into our hotel in the historic centre of Anghiari. Later, a gentle stroll takes us through this charming town, and we explore a little of the local history. We enjoy an aperitif before dinner in a nearby restaurant.
Day 2
After breakfast, we drive to Sansepolcro to see another celebrated painting by Piero della Francesca. A beautiful hike follows a low ridge of the Alpi della Luna, with views across the Tiber Valley, leading to the evocative Franciscan convent and hermitage at Monte Casale where we have our picnic. Time to visit the hermitage before returning to Anghiari, where there is time to browse the shops before dinner in a local restaurant.
(6 km/3.8 miles)
Day 3
Today we leave Anghiari, and a short drive takes us across the border into Umbria. We start our walk high above the town of Città di Castello and hike through open farmland and woods, passing abandoned stone houses and a dramatic fort to a small chapel where we enjoy our picnic lunch. We continue on foot to arrive at the stunning Abbazia San Faustino, a beautiful small hotel converted from a former abbey with spectacular views over the Umbrian hills. Dinner tonight is in the hotel restaurant.
(17 km/11 miles)
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.
(8 km/5 miles)
Day 5
We depart San Faustino, and a short drive takes us into the foothills of the Apennines. Here we follow trails past remote farmhouses and through woods to arrive at the Basilica of San Ubaldo, perched on a hill above the lovely medieval town of Gubbio. After visiting the Basilica, we continue on foot down through the cobbled streets to arrive at our delightful four-star hotel in the heart of Gubbio, overlooking the main square. We use this as our base for the final 3 nights of the holiday. Dinner tonight is in a local restaurant.
(19.5 km/12 miles)
Day 6
Today a short drive takes us to the thirteenth-century Benedictine abbey of Montelabate, formerly one of the most important abbeys in the region. We enjoy an exclusive guided tour before a light lunch including wine, cheese, and olive oil from the estate. Later in the day, there is time to explore Gubbio and visit the town’s museum displaying the precious Iguvine Tablets, which date back to the 3rd century BC. In the evening, we experience a unique medieval-style banquet prepared by a local chef in a private country house, a short drive from Gubbio.
Day 7
Our final hike takes us to the Monte Cucco National Park, a short distance from Gubbio. Starting from a high alpine meadow at 1132 m, we climb up through beautiful beech woods to emerge above the tree line at just above 1400 m. We circle the summit of Monte Cucco, enjoying spectacular views across the Umbrian hills and to the coast of Le Marche. We picnic in the alpine meadow before returning, by van, to the hotel. In the early evening, we take our seats in the town square for the annual Palio of the Balestra, a celebration of flag-throwing and medieval pageantry, culminating in a crossbow competition between Gubbio and Sansepolcro. Our final dinner is in a fabulous local restaurant.
(6.7 km/4.2 miles)
Day 8
Return to Arezzo train station for 11:00 am.
