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Italy: Umbria

Undiscovered Villages of Umbria Walk

Trip code: W07UR

Average customer rating 4.7 / 5(23 verified reviews)

Self-Guided Walking
7 nights hotel-to-hotel
Moderate
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

Italy’s ‘green heart’: boundless olives groves, verdant vineyards, flower filled towns, panoramic medieval villages

Follow in the footsteps of St Francis along the ancient pilgrimage trail

UNESCO Assisi, spectacular Spoleto, medieval Bevagna, stunning Montefalco – the balcony of Umbria

Impressive limestone gorges, rare flora and fauna in the Monte Subasio Natural Park

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Trip details

This 7-night linear trip is a fantastic mix of wonderfully scenic walking, historic towns and panoramic hilltop villages. The walks follow a mix of quiet country lanes, paths and trails, using in part the St Francis’ Way – so called after the route the saint took on his final visit to Assisi in 1226 – and the ‘Sentiero degli Ulivi’, the Olive Grove Trail. Along the way, admire the stunning valley vistas from the slopes of the ‘bald mountain’ Monte Subasio, discover the secluded hermitage of St Francis nestled amongst ancient oak forest, pass through olive groves that date as far back as Roman times and wander around the evocative centro storico of the walled town of Bevagna.

What's included

Included

  • 7 nights in 4-star equivalent, 3-star and 4-star accommodation
  • All breakfasts
  • Headwater navigation app
  • Luggage transfers between hotels
  • Walking transfers on days 4 and 5

Not included

  • Flights
  • Travel insurance

Travel options

Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in Assisi

Arrive in Assisi

Explore the UNESCO St Francis’ basilica and the town’s many other sights.

You stay at Hotel Porta Nuova

Exterior of the Hotel Porta Nuova

Hotel Porta Nuova

Assisi

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Mastercard
  • Minibar
  • Shops
  • Television
  • Visa cards

Located a stone’s throw from Porta Nuova – one of the main medieval gates into Assisi’s Old Town – the family run Hotel Porta Nuova comes with a contemporary design and modern, well appointed bedrooms. There is a lounge and panoramic terrace on the first floor, where you can relax with a drink whilst admiring the rolling, verdant Umbrian hills.

Day 2 · 12km/7.5mi or 16km/9.9miAssisi to Spello

Assisi to Spello

Set off across the olive grove clad slopes of Monte Subasio, enjoying the gorgeous view below. If doing the longer option, pause at the Hermitage of St Francis, the saint’s historic retreat, before traversing a mountain trail to Spello, the town of flowers, famous for its annual Infiorita festival when the streets are carpeted in colourful floral mosaics. The shorter version (elevation chart below) follows the Via degli Ulivi through the foothills of Monte Subasio with stunning valley views as you go.

Elevation

Assisi to Spello elevation profile

You stay at Albergo il Cacciatore

Albergo Il Cacciatore, Spello
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Albergo il Cacciatore

Spello

  • Air conditioning
  • ATM
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Television
  • Visa cards
  • Wifi access

A warm welcome is guaranteed at the Albergo il Cacciatore (the hunter!) as the hotel has been in the same family for over 50 years. Located in Spello’s Old Town, there’s a lovely terrace with an amazing, far reaching view over the valley. Bedrooms here are airy and spacious with a traditional Italian design.

Day 3 · 14km/8.7miAt Spello - Collepino loop walk

At Spello - Collepino loop walk

Follow a beautiful path along a Roman aqueduct to the cobbled streets of the hilltop, pink hued village of Collepino. Then it’s a panoramic downhill walk through olive groves back to Spello.

Elevation

At Spello - Collepino loop walk elevation profile

Day 4 · 13km/8.1mi or 17km/10.6miSpello/Sassovivo to Trevi

Spello/Sassovivo to Trevi

We take you (20 mins) to the perfectly restored Benedictine abbey of Sassovivo, then walk on the appropriately named Sentiero degli Ulivi through woodland and olive groves to the hilltop village of Roviglieto, before descending to Trevi for a picture-postcard view of this Roman gem on the slopes of Monte Serano. Discover this old theatre town with remnants of the Mura Romana (Roman Wall) and Mura Medieval (Medieval Wall) still encircling the town.

Important Information: {NEWLINE}For 2026, we have made a small adjustment to the itinerary following the temporary closure of the Hotel Antica Dimora. Instead of staying in Trevi, you’ll enjoy an extra night in both Spello and Spoleto, with transfers included at the end of day 4 from Trevi to Spello and the beginning of day 6 from Poreta to Trevi. This ensures you’ll still have plenty of time to discover the beautiful medieval town of Trevi.

Elevation

Spello/Sassovivo to Trevi elevation profile

You stay at Hotel Antica Dimorra alla Rocca

Room at the Antica Dimora alla Rocca, Trevi
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Hotel Antica Dimorra alla Rocca

Trevi

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Swimming pool
  • Television

The Antica Dimora alla Rocca is housed in 4 different historic buildings which date back to 1650, built by an aristocrat for his eldest son. The buildings have been restored and renovated to a high standard. The decor keeps with the elegance and architecture of 17th century, the rooms feel grand and luxurious with frescoed ceilings.

The hotel offers a large buffet breakfast which in good weather can be taken on the terrace. The hotel has a small pool and terrace where you can catch the late sun in the afternoon.

Day 5 · 9km/5.6miAt Trevi - Bevagna to Montefalco Walk

At Trevi - Bevagna to Montefalco Walk

A transfer this morning (25 mins) to the walled town of Bevagna, home to the 13th century Gothic Palazzo dei Consoli, the golden theatre and Roman temple and baths. Explore this lovely town then make your way through a patchwork of olive groves and vineyards to the hilltop wine village of Montefalco. Wander round its medieval streets, admire the superb views and enjoy wine tasting in one of the many Sagrantino wineries. Transfer and overnight in Trevi.

Elevation

At Trevi - Bevagna to Montefalco Walk elevation profile

Day 6 · 12km/7.5miTrevi to Poreta

Trevi to Poreta

Join the ancient St Francis’ Trail to amble along to the hillside with stunning views of the valley of Spoleto to the church of Madonna di San Arcangelo. Pass the secretive Eremo Francescano (Convento Pissignano) before heading to the tiny medieval village of Poreta, with the ruins of its 10th century castle still standing guard.

Elevation

Trevi to Poreta elevation profile

You stay at Agriturismo Borgo della Marmotta

Pool at Borgo della Marmotta
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Agriturismo Borgo della Marmotta

Poreta

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Shops
  • Swimming pool
  • Television
  • Visa cards

Borgo della Marmotta is not just a hotel. Borgo means ‘village’ in Italian and this wonderful location is more like a hamlet than a hotel. In fact, the hotel has been built by restoring the buildings that were left unoccupied from a 17th century village. Located next to the tiny hamlet of Poreta, the restoration has breathed new life into the tiny village restoring the granary, the stables, the mill and even the sheep barn – now home to the hotel’s restaurant – to create a luxurious, relaxing retreat in the beautiful Umbrian countryside.

Today the hotel offers airy rooms, a swimming pool, lovely grounds and a terrace with wonderful views.

Day 7 · 14km/8.7miPoreta to Spoleto

Poreta to Spoleto

Pick up the St Francis’ Trail as you make your way through olive groves and tiny medieval villages to Spoleto. Stroll along the impressive 14th century viaduct that bridges the valley to enjoy the spectacular views and discover the town’s Roman arch, Roman theatre and 12th century Duomo.

Elevation

Poreta to Spoleto elevation profile

You stay at Hotel dei Duchi

Hotel dei Duchi, Spoleto
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Hotel dei Duchi

Spoleto

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Television
  • Visa cards

Boasting a prime location in the centre of Spoleto’s historic centre, the Hotel dei Duchi panoramocally gazes out over the town’s Anacajani Park, the Roman theatre and St Agatha’s monastery. Inside, the hotel is stylish and modern, with a lounge and terrace – which benefit from the lovely views – bar and 2 restaurants. Bedrooms at the Hotel dei Duchi are contemporary and comfortable, with views over the valley, the garden or the Roman theatre.

Day 8 · —Leave Spoleto

Leave Spoleto

Extending your holiday

Exterior of the Hotel Canada Roma

Hotel Canada Roma

Rome

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Safe
  • Shops
  • Tea & coffee

The 3 star Hotel Canada Roma is centrally located near the main railway station, making it an excellent base from which to explore Rome. Each room is ensuite and has been lovingly decorated in an elegant Italian style complete with vintage furniture. Rooms come with tea and coffee maker as well as air conditioning and safe.

This well appointed hotel also boasts a bar for pre dinner drinks and nibbles, as well as an external courtyard where you can savour a drink under the stars.

What our travellers say

The Hidden Villages of Umbria holiday is wonderfully designed. The locations are stunning and there are countless panoramic views. All the people we met were friendly and helpful. The food is great too. Get food for picnics on your walk from local alimentari, or anywhere that advertises panini. If you have a pre dinner drink in a bar, it will probably come with snacks. Try the scrambled eggs with truffles. Look out for wild boar on your walks – we saw some on the first walk. We would also recommend adding a day in Assisi at the beginning of the trip, As ever, Headwater were able to accommodate our extra request. They are a pleasure to deal with!

Jean Evanson

Although it was quite expensive vacation for us we had a lovely holiday which was, overall very well organised by Headwater who were always available when we were unsure about any aspects of the journey.

Diana Bird

The holiday was great. Loved the flexibility of Headwater for allowing us to spend extra time in Rome. The walks were very good wrt length, difficulty, maps, navigation etc. I noticed during the holiday there were different hotel options and next time I might focus a bit more on which ones. Having said that, we got a good range of places to stay and the B&B basis worked perfectly for us (except in Porteta) which is in the middle on nowhere and therefore the restaurant being open was rather crucial.

James Turner

Very well organised and enjoyable. App is excellent. Makes old style paper and map itineraries obsolete.
Very proactive and helpful service. Would definitely use again

William Holmes

Headwater were very thorough and very professional. Any problems we had weren’t their fault.

Geoffrey Baggaley

It was a lovely trip, the first walk was arduous and the app misguided us …. But we loved the whole trip . Staff were on hand to help if we needed it .

Louise Richards

Superb pre-booking service and excellent walking app. Would have benefited from a bit more guidance on good things to do at the various places that we stopped on the walk. Obviously we can google this ourselves, but actual feedback from people doing the trip would have been valuable.

Michael Darvell

Headwater Holidays was very helpful in advising on our choice of walks and responsive to our questions in planning our holiday. The trip was well designed, accommodations were excellent and the app was flawless. Written material on sites and history was thorough and informative. Each day of our walk on the St. Francis and Olive Grove Ways was magical. We are delighted now to plan our next walk with Headwater.

A Valued Customer

All arrangements went smoothly, the hotels, luggage transfer and app all worked perfectly

Mrs Spargo

All the boxes ticked, once we all got used to the ap, with only one hiccup all went as planned, and good weather

A Valued Customer
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Positive impact

Carbon score for this trip

11.0

Kg CO₂e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more

From£1,149per person