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Medieval Umbrian Cycling

Medieval Umbrian Cycling

1-800-267-3347 Email us
  • Holiday typeSelf-guided cycling
  • Duration10 nights
  • Accommodationhotel-to-hotel
  • Activity level
  • From $2385per person, tour only
  • Departures
    Every two days from 27 May '19 to 22 Oct '20
  • What your holiday price includes
  • 10 nights hotel-to-hotel accommodation in a mix of and hotels
  • Continental breakfast and 6 evening meals
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality hybrid bikes
  • Standard transfers at the start/end of the trip
  • Luggage transfers between hotels
  • Optional Upgrades
  • Electric bikes available
  • Room upgrades and extra nights at selected hotels
  • City break add-ons in Rome and Perugia
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, solo travellers, couples
      from 13 reviews

Mr Laxen says...
We really enjoyed our holiday, but because we chose the 10 day option, which included 4 nights in the hotel we liked least, Albergo La Macchia (all other ...
Read reviews »

Italy: Umbria

Mediaeval Umbrian Cycling

  • Totally unspoilt cycling: olives, sunflowers, vineyards and apricot orchards
  • Gorgeous summer climate, soft terracotta colours, sun-drenched landscapes, panoramic views
  • Friendly, high quality hotels, most with private swimming pool; superb cuisine, amazing value wines
  • Beautiful hilltop villages and hamlets, each with its own hidden treasures
  • Assisi - jewel in the Umbrian crown; gorgeous Spello, Etruscan Perugia, medieval Montefalco
  • Four nights in the fascinating historic city of Spoleto

Few places can stir emotions quite as intensely as Umbria. To visit here is to embark on a journey into a timeless world of sun-drenched landscapes, ancient hill villages and some of the friendliest people we've ever met.

This 10-night self-guided cycling holiday combines scenic pedalling through olive groves, sunflower fields, vineyards and apricot orchards with the chance to explore some of the most fascinating towns and historic villages in the country. You'll freewheel along the stately Roman Via degli Ulivi and follow in the footsteps of emperors at the sacred springs of Campello sul Clitunno.

Highlights include the lovely hilltop wine village of Montefalco, 'the balcony of Umbria', and the fascinating historic city of Spoleto crammed with exciting Roman remains including Emperor Vespasian's mother's house, and fascinating original atrium, baths and mosaics. And, of course, no trip here would be complete without spending time in magical Assisi - be sure to visit St Francis' Basilica with its beautifully ornate frescoes and his peaceful forest retreat on Monte Subasio where he used to stroll and preach to the birds.

The hotels we've selected for this holiday are pretty special too, ranging from a stunningly restored ancient hamlet, set in its own manicured gardens, to a panoramic 4 star hotel in Spello with a gourmet restaurant and one of the most prestigious wine cellars we've ever stumbled upon!

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

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 at Spello

We meet you at Foligno station and take you (15 mins) to picturesque Spello in time for dinner in your hotel's atmospheric restaurant.
You stay at La Bastiglia Hotel (breakfast and evening meal)

Day 2: Spello to Spoleto 50km/31.5mi

Today is level cycling most of the way along the Teverone Valley with some of the best views of the week. We strongly recommend the short uphill detour to Trevi, a beautiful hilltop village dating back to Roman times and capital of the Umbrian olive oil industry. Finally your hotel is situated in the centre of Spoleto near to all the museums and restaurants.
You stay at the Hotel Charleston (breakfast included)

Day 3-5: At Spoleto

Pretty hilltop Spoleto and the surrounding area offer a wealth of things for you to do on your 4 night stay here. The city of Spoleto has a wonderful history reflected in its Architecture dating back to the Etruscans, and including a Roman Amphitheatre, 10th century Church, 12th century Duomo and a 80m high 14th century aqueduct. The castle here was a former prison and now houses an impressive art museum. Lots of lovely cobbled squares crammed with traditional trattorie for lunch. You can also take the train to the Emerald City of Rome. For those wanting to be more active why not walk the well signed trail up Spoleto's Monteluco. As you climb the views of the Vale of Spoleto are certainly impressive. Or walk along the famous Spoleto - Norcia railway now a peaceful Via Verde taking you on a journey through the magical Valnerina. For cyclists take a ride passing pretty villages, olive groves and flowering meadows. In July you can also attend the Two Worlds Festival - a celebration of Classic and Opera music.
You stay at the Hotel Charleston (breakfast included)

Day 6: Spoleto to Marcellano 44km/27.mi

The wines of Montefalco are known throughout the world, in particular the fine red Sagrantino. There is a climb up to the old village itself, 'the Balcony of Umbria', but you are well rewarded with wine-tasting, magnificent views and beautiful medieval streets. Continue from here past lush green fields, poppies and buttercups before your last climb up to the medieval village of Marcellano. Your 4 star hotel is set within its own lovely gardens - fabulous panoramic views across the entire valley.
You stay at the Grand Relais Laurenti (breakfast and evening meal)

Day 7: At Marcellano

It's tempting to spend the day relaxing by the pool in the hotel's tranquil grounds, but it would be a shame to miss the Roman walled town of Bevagna (10 mins by taxi; or you can cycle) - Umbria's hidden gem. Visit the 13th century Gothic Palazzo dei Consoli, the golden mediaeval theatre, or the 2th century Roman temple and baths that include a spectacular lobster mosaic. Alternatively, you can opt for a circular cycle to Ceralto Castle.
You stay at the Grand Relais Laurenti (breakfast and evening meal)

Day 8: Marcellano to Torgiano 42km/26.5mi

It's picture perfect views all the way this morning as you arrive at the impossibly photogenic mediaeval village of Gualdo Cattaneo with its imposing 15th century castle and 13th century crypt. There's a downhill whizz before gentle, flat cycling across the plain and a final short ascent into the old wine town of Torgiano, famous for its Lungarotti cellars.
You stay at the Hotel Al Grappolo d'Oro (breakfast at the hotel, evening meal at a local restaurant)

Day 9: At Torgiano

There is a dedicated wine and olive oil museum - with tastings - in Torgiano's pretty centro storico. Alternatively it's a short bus or taxi ride (approx 15 mins) to the university town of Perugia, famous for one of Italy's finest art collections and home to the renowned Baci chocolates. For the more energetic we provide route notes for optional cycle rides to the panoramic town of Bettona, which dates back to Etruscan times, or the capital of painted ceramics, Deruta.
You stay at the Hotel Al Grappolo d'Oro (breakfast at the hotel, evening meal at a local restaurant)

Day 10: Torgiano to Spello 43km/27mi

Your last day's cycling takes you along the 'Wine and Art Road' to Brufa - lovely views of Perugia and Assisi - and on through the Chiascio Valley, on country lanes passing sunflower fields, ochre coloured farmhouses and meadows redolent with wild apricots and figs. There's time to visit spectacular Assisi - the beautiful Piazza del Comune, the 13th century Giotto frescoes and of course, the UNESCO recognised Saint Francis' Basilica - before cycling on along the lovely traffic free Via degli Ulivi and through olive groves back to Spello.
You stay at La Bastiglia Hotel (breakfast and evening meal)

Day 11: Leave Spello

Leave Spello after breakfast for your flight home. Alternatively, perhaps spend extra nights in Rome - we can easily arrange these for you.

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. If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day.

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.

Albergo La Bastiglia Hotel, Spello

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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: Deluxe Room or Junior Suite
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.

Extra nights: Please contact us for details.

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

Hotel Charleston, Spoleto

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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.

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

Grand Relais Laurenti, Marcellano

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Just outside the walls of the pretty hilltop village of Marcellano lies the supremely welcoming Grand Relais Laurenti, where nothing seems to be too much trouble. A recently restored former convent (formerly known as the Palazzo Gradoli), parts of the hotel date to as far back as 1516. Opened in 2006, the owner Laurenti Torrello spent thirteen years restoring the premises in order to ensure that all work was done to a suitably high standard. The well put together rooms have a distinctly cosy feel to them and retain original features such as the wooden beams on the ceilings.

In addition to the hotel, the Grand Relais Laurenti owns 90 hectares of the surrounding land which is used by their own farm to raise livestock such as cattle and lamb to supply the restaurant with meat. They also produce their own olive oil from their own olive groves and pride themselves on their ability to source only the finest ingredients (such as truffles and porcini mushrooms) from the surrounding area. The restaurant itself has two chefs who provide a mixture of traditional regional food and more elaborate international fare.

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

Hotel Al Grappolo d'Oro, Torgiano

Swimming Pool IconHair dryer iconNEARBY:

Situated in the centre of the medieval town of Torgiano is Al Grappolo d'Oro (The Golden Bunch of grapes), a recently restored 19th century residence. The hotel has 15 rooms, each individually decorated in a modern style with warm colours and furnished to a high standard, offering a cosy, welcoming stay. The art filled reception/lounge area gives the hotel character from the start but features such as the pool in the garden to the rear and the downstairs bar (along with the well-stocked breakfast buffet) mean that despite the B&B nature of the hotel, there is still the possibility to spend time relaxing here during the day.

The owner Antonello Rossi also owns the wonderfully traditional Italian restaurant 'Siro', which lies around 300 metres away from the hotel and where evening meals will be taken.

Room upgrades: Junior Suite.
Junior Suites are more spacious with ample and bright, classic furniture and wooden floors.

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

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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.

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

Hotel Fortuna, Perugia

Hair dryer icon

The traditional 3 star Hotel Fortuna is set right in the heart of the historic city. The building itself dates to the 14th century and was tastefully renovated in the early 1990's. There are still some original features - look out for the arched windows downstairs. All rooms are en suite with satellite TV, telephone, minibar and radio. There is a roof garden terrace - great views over the city and a bar/ lounge area. The hotel has also recently added a gym


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

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


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 Laxen, 23/10/2016

We really enjoyed our holiday, but because we chose the 10 day option, which included 4 nights in the hotel we liked least, Albergo La Macchia (all other hotels were 2 nights) we ended up being disappointed with this part of the trip. On one of our days off we took a train from Spoleto (very easy, but remember to validate tickets) to do a one day visit to Assisi (get the bus from the station to the last stop then walk down through Assisi), rather than stopping off for a short time on the last leg of the cycling. It was better to have a relaxing time to wander through Assisi. We will will certainly be thinking about another Headwater holiday.

Mr Hodgson, 15/10/2016

Enjoyable relaxing holiday, with good mix of activites, beautiful scenery,great food and comfortable hotels, highly recommended!

Ms Skinner, 27/09/2016

They said we were mad- ' too hot!', ' too hilly!' ' too far' - they were wrong! We went in August and we are both only moderately fit and over 60. We have never enjoyed a holiday so much. Because you are cycling there is always a breeze. I would recommend taking ' camelpacks' ; these helped us to drink enough water and kept the water cool. Together with factor 50 liberally applied in the morning we never burned nor were we uncomfortable.

There was always a place to grab a juicy nectarine, cheese and bread en route and a swim at the end of the day before delicious evening meals in all the hotels.

We were greeted like royalty and slept like babies. I am officially in love with Italy.

So , any improvements? Yes, we went awol from Torgiano so that we could spend a whole day in Assisi. Assisi is so beautiful that it deserves more than a quick exhausted ramble in the middle of a cycle so, personally I would have preferred to stay closer to the this wonderful town rather than in Torgiano which was rather small and a little uninteresting.

Spoleto is also stunning and we extended our holiday both here and in Rome. Can't wait for the next one.... Now to choose.

Mrs Chessum, 23/06/2015

We had a very good time. It was a lovely holiday marred only by the directions being a little bit unreliable.

Mrs Roberts, 22/06/2015

The holiday was well organised and gave us what was promised in the brochure. When we did run into problems ( minor and not the fault of Headwater) they were sorted out with the minimum of fuss and delay ( eg puncture as above and then BA cancelled our flight home from Rome with 48 hours notice! We contacted Vlad in resort and he immediately contacted Michelle Roberts in UK who sorted out alternative flight for us. Without such prompt and efficient service we would have had an anxious and stressful 2 days- not what you want on holiday!

The hotels were great- obviously hand picked- lovely rooms ,pools , food - everything. The routes were great although on occasion the notes were unclear. Also as one person wrote in the blue book- Italy- wonderful country- shame about the maps!! But a great holiday and only minor nit picks!

Mr Collins, 24/10/2014

Headwater offers a very efficient and reliable service. The equipment was very good, the hotels were on the whole very agreeable, at a price. We travelled off season, but even so, the hotel restaurants were extremely busy and there were occasions when we had to wait so long, we gave up on the puddings!

Overall the cycling was most pleasant on quiet roads, very often for cyclists and walkers only. There were some demanding climbs into any town worth its salt in tourism, but then there was the added bonus of the long descent back down to terra firma. The weather was amazingly good and the lovely tranquil scenery.

Mr Cobbold, 23/09/2014

The cycling can be very challenging in this area.

Mrs Gapper, 10/07/2014

The cycling was good with varied scenery and interesting villages and towns. The route notes sometimes need careful interpretation using the area maps and a degree of common sense. however it is easy to go wrong which we did on a couple of occasions.One of the hotels, unfortunately the one we had opted to stay four nights, we thought was sub standard in terms of service and quality and choice of food. Generally the hotels were well located, clean and comfortable. We had a little trouble with two of our four bikes which either required urgent attention by the rep or we managed to borrow a tool from a garage. On previous holidays our Headwater bikes have been trouble free.

Mr Wright, 22/10/2013

Javier is an excellent rep. September is a great month for this sort of holiday - warm but mostly manageable temperatures for cycling. There is a great variety of places to visit and some delightful landscapes. From Il Poggio we had an excellent ride up to Gualdo Cattaneo but it's a bit of a slog - the view from the tower is good. From Relais de Ripa it's worth visiting Perugia on the 'day off' by bus after an early breakfast - don't even think of cycling there unless you are super fit. We also enjoyed visiting Montefalco and the olive and wine museums at Torgiano. We loved the variety of hotels and the meals and warm welcomes from the staff. Headwater have helped us to fall in love with Italy.

Dr Murphy, 04/10/2013

A lovely way to be relatively guilt free enjoying great food and fine wine, and working off the calories by day! Most cycling is relatively flat, but all the fantastic views come at a price - either a short steep climb or a long slow climb!

Mrs Dickinson, 22/09/2013

Some demanding hills but mostly flat cycling. Hotels very varied but all had wonderful views and good food.

Mrs Huddart, 18/09/2013

Headwater provided some lovely, quiet, cycling routes in what is perhaps not the most sparsely populated area of Italy. Montefalco, Bevagna and Assisi were the highlights. Definitely the easiest cycling we have done with Headwater. Knowledgeable rep. The food in all the hotels is excellent (I think more of me came back than arrived!). Hotel at Ripa is the best (but not much to do around it), rooms at Il Poggio are not of the same standard as appear on their website (raised separately with Headwater), views from this hotel are marvellous.

We did feel that the 8 day version of this holiday might have been better as the 4 night break at Spoleto was a little too soon in the holiday (directly after Spello), but this is personal preference.

Altogether an enjoyable holiday with some excellent food.

Mrs Sansbury, 18/06/2013

Very enjoyable, beautiful region, mostly gentle cycling which I loved, historically very interesting.

The only problem was the bike. Though very sturdy, it is the second time with Headwater that I could not fully elevate the handlebar because the brake cables were TOO SHORT. As I am 6' foot tall with long legs the saddle was on the same height as the handlebar which pitched me forward and caused certain anatomical areas to be in discomfort!

This happened on my last holiday with Headwater and although I asked them to prepare a bike with a REALLY adjustable handlebar I still had the SAME problem. Please assemble bikes with LONGER brake cables!!!!!!!!!!

Otherwise what is the purpose of having an adjustable handlebar which CANNOT be raised to requirement!

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.

This 10 night self-guided cycling holiday includes:

Hotel-to-hotel accommodation in a mix of and hotels

Continental breakfast and 6 evening meals

Services of your local Headwater Representative

Headwater Wine Collection Service

GPS route directions and maps

RideWithGPS navigation app

High quality hybrid bikes

Standard transfers at the start/end of the trip

Luggage transfers between hotels

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.

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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 cycling Managed locally by Headwater appointed rep.

Every two days from 27th May 2019 to 22nd Oct 2020, for 10 nights. All dates are subject to availability, please contact us to check.

Continental breakfast and 6 evening meals

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £190 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Tailor-made travel

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

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.

Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for . Simply complete the form below (fields marked * are mandatory) and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.

Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.

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We've been creating high-quality relaxed activity holidays since 1985 and our wealth of experience means we're able to build the perfect tailor-made tour for you. Our 'Gold Trusted' rating on Feefo, the independent review site, underlines our exceptional levels of customer service, and our ATOL bonding and ABTA membership guarantees your holiday is safe with us.