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Walking the Olive Trails of Umbria

Walking the Olive Trails of Umbria

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  • Holiday typeSelf-guided walking
  • Duration10 nights
  • Accommodationhotel-to-hotel
  • Activity level
  • From $2175per person, tour only
  • Departures
    Every two days from 13 Apr '19 to 22 Oct '19
  • What your holiday price includes
  • 10 nights hotel-to-hotel accommodation in a mix of and hotels
  • All continental breakfasts and 6 evening meals
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service
  • Route directions and maps
  • Standard transfers at the start/end of the trip
  • Luggage transfers between hotels
  • Optional Upgrades
  • City break add-ons in Rome
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, bird spotting opportunities, art & history, swimming opportunities, solo travellers, couples, high peaks
      from 3 reviews

Mr Leighton says...
An excellent way of exploring a beautiful part of Italy.
Read reviews »


Walking the Olive Trails of Umbria

  • Discover Italy's 'Green Heart': deep lush forests, hidden hermitages, endless olive groves and the flora and fauna of the Monte Subasio Natural Park
  • World-famous Assisi, the jewel in the Umbrian crown; Spello, one of Italy's best preserved towns; Trevi and Spoleto, hilltop towns completing a daisy-chain of mediaeval marvels
  • Exceptionally friendly hotels - two with swimming pools - including a converted 17th-century palazzo and a luxury 'farm resort'
  • Superb regional cuisine: freshly prepared pastas, highly prized black truffles, the finest of olive oils, famous Sagrantino wines

This 10-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way, you explore the upper slopes of the 'bald mountain' Monte Subasio with stunning mountains vistas. You can discover the secluded hermitages of St Francis, pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.

The walking is beautifully unhurried, retracing in part the trail St Francis took on his final visit to Assisi in 1226. It's a rural route brimming with rare flora and fauna, passing through olive groves dating back to Roman times. Stroll along pilgrimage trails through centuries-old forest and sacred woodland that has for years been tended and cared for by the Franciscan monks.

You stay in beautiful mediaeval towns: Assisi 'the town of St Francis' with its UNESCO-listed basilica; pretty Spello, which lies on the other side of Mount Subasio from Assisi; Trevi, standing on its hill overlooking the plains of Campello; Poreta, a tiny village with a restored hilltop castle and church, and finishing in Spoleto - the town of the amphitheatre and aqueduct.

The hotels we've chosen are special too. From Renaissance-style palaces in Assisi and Trevi to a chic renovated farmhouse in Poreta. Food of the region is rustic, often called 'cucina povera'. The most typical pasta dish is Stongozzi, served with black truffles or a spicy tomato sauce, followed by simple grilled local meats and then a slice of pecorino cheese washed down with some superb wines. Sagrantino di Montefalco or red from Torgiano are just a sample. For a picnic lunch why not try the Umbrian staple, the porchetta sandwich - roast pig stuffed with herbs

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

Walking information

The paths you follow are generally waymarked and well maintained. As there are frequent ascents and descents, you need to be reasonably fit and confident. Walking boots are essential and walking poles are recommended (but only if you already use them).

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Day 1 Arrive in Assisi

Arrive at your hotel, where you'll stay for three nights. (Staying at Hotel Fontebella Palace, Breakfast only)

Day 2 Valfabbrica to Assisi 14km/9mi/4hr

A short transfer to pick up the Via San Francesco pilgrims' trail. Stroll through peaceful oak and pine woods and enjoy superb views as you approach the ancient town of Assisi. Call in at the San Croce chapel with its three-arched Ponte dei Galli, finishing off on a manicured trail through a 1,000-year-old forest to the majestic Basilica di San Francesco. (Staying at Hotel Fontebella Palace, Breakfast only)

Day 3 At Assisi

Visit the basilica with its magnificent C13 Giotto frescoes and the commanding hilltop castle. Amble up Via San Francesco to the beautiful Piazza del Comune to visit the well-preserved temple of Minerva. (Staying at Hotel Fontebella Palace, Breakfast only)

Day 4 Assisi to Spello 16km/10mi/5.5hr

Climb up Monte Subasio to the Hermitage of Asissi. Traversing a trail along the mountain you get unforgettable views of the Vale of Spoleto, before heading down into delightful Spello and your hotel for two nights. (Staying at Albergo La Bastiglia, Half Board)

Day 5 At Spello

Pink-stoned Spello is a well-preserved Roman town, with beautiful town walls, ruins of the old theatre and amphitheatre and thermal baths. Visit the church of Santa Maria Maggiore with its outstanding frescoes by Pinturicchio, the town's art gallery, annexed to the church, and the Palazzo Comunale Vecchio (Old Town Hall). Or perhaps take the train to Perugia the region's capital. (Staying at Albergo La Bastiglia, Half Board)

Day 6 Spello/Sassovivo to Trevi 16km/10mi/5hr

A short transfer this morning - Then follow the Sentiero degli Ulivi - the Olive Grove Trail - that connects Spoleto to Assisi. Spend time at the beautifully-restored cloistered Abbey of Santa Croce di Sassovivo and continue through woodland and olive groves to the hilltop village of Roviglieto - the highest settlement on the trail at 700m. Descend to Trevi for a picture-postcard view of this Roman gem on the slopes of Monte Serano. You'll stay here for two nights, and enjoy dinner (included) under the church tower in the atmospheric Piazza della Rocca. (Staying at Hotel Antica Dimora, Half Board with wine included)

Day 7 At Trevi

Explore this old theatre town with remnants of the Mura Romana (Roman Wall) and Mura Medieval (Medieval Wall) still encircling the town. The Teatro Clitunno is still one of the town's most important gathering places. Visit the Olive Oil Museum, housed in an ex-convent, and stroll around the main square, home to the C14 Palazzo Comunale. (Staying at Hotel Antica Dimora, Half Board with wine included)

Day 8 Trevi to Poreta 15km/9.5mi/4.5hr

On the shared Olive Trail and Francesco Way, amble along to the hillside church of Madonna di San Arcangelo. Pass the secretive Eremo Francescano (Convento Pissignano) and explore the ruins of C10 Castello di Campello Alto. Then meander down to Poreta and your hotel for the next two nights, where dinner is included in the converted stables. (Staying at the Borgo della Marmotta, Half Board )

Day 9 At Poreta

Borgo della Marmotta is a perfect place to unwind for a day or two. Relax on a lounger by the pool with a good book, soak up the sun in the hotel gardens, or pamper yourself with one of the wellness sessions. Or follow small country roads down to the village of Campello sul Clitunno and visit the Roman Springs and temple of Clitunno. (Staying at the Borgo della Marmotta, Half Board )

Day 10 Poreta to Spoleto 15km/9.5mi/4.5hr

Pass through the typically Umbrian villages of Santa Maria Reggiano, Bazzano and Eggi. From Eggi, the St Francis Way leads you along back lanes to the bustling town of Spoleto. Or take the old Olive Trail high up onto the former railway line that used to run from Spoleto to Norcia. Cross the 60m-high Cortaccione Viaduct for a superb view back over your week's walking. (Staying at the Hotel Charleston, Breakfast only )

Day 11 Leave Spoleto

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Fontebella Palace, Assisi

Hair dryer iconNEARBY:

Hotel Fontebella features a period, Renaissance style throughout the establishment and enjoys an exquisite view of a beautiful Umbrian valley. Free Wi-Fi is available throughout. Hot tubs and sauna available. You can choose different kinds of views, over the Umbrian Valley or over Assisi city centre.

Buffet breakfast is served in the Sala degli Archi, decorated with beautiful brick arches, perfectly preserved throughout the centuries. On site you will find Restaurant Il Frantoio, which is mentioned in the Michelin guide. It has over 300 wines in its cellar and specialises in truffle dishes and homemade pasta.

Room upgrades: Superior room with valley view.
Superior rooms offer more space and a view of the Umbrian Valley.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Albergo La Bastiglia Hotel, Spello

Swimming Pool IconHair dryer icon

The La Bastiglia Hotel boasts a beautiful setting at the foot of Mount Subasio, the enchanted mountain of Saint Francis. Originally an ancient mill the hotel has been lovingly restored and transformed into an unforgettable place to stay. There are 33 rooms divided into three categories, many overlooking the typical Umbrian landscape of cypress trees and olive groves. The restaurant serves a mix of ancient recipes and modern creations using the freshest ingredients. On display inside the hotel there is a collection of ceramics, antique furniture and important paintings from the private collection of Schifano and Norberto.

Room upgrades: Superior Room, Deluxe Room, Junior Suite or Junior Suite Deluxe.
Superior rooms are larger, and have a small balcony and bathroom with shower. Deluxe rooms are larger with a balcony and bathroom with a bath. The Junior Suite includes a Jacuzzi in the bedroom and a panoramic terrace with solarium. The Deluxe Junior Suite can accommodate up to five people and has a private panoramic terrace with table, chairs and sun loungers and a Jacuzzi for 2 people.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Antica Dimora , Trevi

Swimming Pool IconHair dryer iconNEARBY:

The Antica Dimora is housed in a building which dates back to 1650, built by an aristocrat for his eldest son. The building has been restored and renovated to a high standard. The decor keeps with the elegance and architecture of C17, the rooms feel grand and luxurious with frescoed ceilings and all have air con and minibar.

The hotel offers a large buffet breakfast which in good weather can be taken on the terrace, dinner is a gourmet affair, a 4 course menu mixing the best of Umbrian and Mediterranean food, all matched with wine (included). The hotel has a small pool and terrace where you can catch the late sun in the afternoon.

Room upgrades: Deluxe Room.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Castello di Poreta , Poreta

Hair dryer icon

As an alternative to the Borgo della Marmotta, stays can be taken at the Castello di Poreta. Offering stunning views of the Umbrian countryside the C14 Castello di Poreta stands above the vale of Spoleto at an altitude of 470 metres. The castle has been restored to create a rustic atmospheric hotel. The hotel rooms have a chique modern touch, and all have air con. The hotel restaurants serves local specialites and in good weather dinner can be taken on a terrace with a view. Wine is included with your dinner and a packed lunch is provided for the day when you leave the hotel.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Borgo della Marmotta, Poreta

Swimming Pool IconHair dryer icon

Borgo della Marmotta is not just a hotel. Borgo means 'town' in Italian and this wonderful location is more like a mini town than a hotel. In fact, the hotel has been built by restoring the buildings that were left unoccupied from a C17 village. Located next to the tiny hamlet of Poreta, the restoration has breathed new life into the tiny village restoring the Granary, the Square, the stables, the mill and the great outdoor courts. To create a luxurious, relaxing retreat in the beautiful Umbrian countryside.

Today the hotel offers lovely airy rooms, a swimming pool, nice grounds and a terrace with wonderful views. The hotel's restaurant offers an a la carte menu showcasing regional cuisine.

Room upgrades: Superior Room or Suite.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Charleston, Spoleto

Hair dryer iconNEARBY:

Completely renovated in 2011, Hotel Charleston is set in a 17th-century building in Spoleto's historical centre, next to the Modern and Contemporary Arts Museum. Its elegant, individually-decorated rooms feature a modern design. Wi-Fi is free in all public areas. Rooms are individually decorated, and come with exposed wooden beams on the ceilings. Each is equipped with a minibar, and a flat-screen TV with satellite channels. A buffet breakfast is available each morning, and is served out on the terrace in warm weather.

Room upgrades: Junior Suite.
Junior suites are spacious and elegant with seating area, parquet floors and exposed wood beams.

Extra nights: Please contact us for details.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Astoria Garden, Rome

Hair dryer icon

The 3-star Hotel Astoria Garden has a most unusual feature: an internal garden complete with banana and orange trees! Centrally located near the main railway station, but in a quiet residential street, this is a really good base from which to explore. There are 34 rooms, all air-conditioned and recently refurbished. They have telephone, television, and ensuite bathrooms.


Please call our sales team on 1-800-267-3347 or email usa@exodustravels.com to arrange flights and connecting transfers to your hotel.


Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mr Leighton, 18/10/2018

An excellent way of exploring a beautiful part of Italy.

Mr Tomkinson, 12/10/2018

The holiday was well organised and the reps. were friendly and helpful. All of the towns visited were interesting but some of the walks lacked interest and the walk from Spello to Trevi was more demanding than expected with a succession of hills. The walk instructions were excellent, you hardly needed the map.

Mr Fowler, 17/09/2018

Overall very enjoyable .

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

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The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Please contact us for child prices.

Holiday type
Self-guided walking Managed locally by Headwater appointed rep.

Every two days from 13th Apr 2019 to 22nd Oct 2019, for 10 nights.

All continental breakfasts and 6 evening meals

Tailor-made travel

Tour only
Transfers included from Foligno train station at 17:15, and back to Spoleto train station at 10:30.

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

We are ATOL registered We are an ABTA member
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