
Mediaeval Umbrian Cycling
This 10-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages with 4 nights spent in Spoleto with its fantastic architecture and opportunities to visit Rome and Norcia, famed for its cured meats.
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Reviews 14 Reviews5/5
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Vacation Style Holiday Type
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Cycling
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Self Guided
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Activity Level Moderate
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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!
- 10 nights accommodations
- Continental breakfast and 6 evening meals
- Services of your local Headwater Representative
- GPS route directions and maps
- RideWithGPSÂ navigation app
- High quality hybrid bikes
- Luggage transfers between hotels
- Flights
- Arrival & departure transfers (available on request, inquire for supplement)
- Room upgrades and extra nights at selected hotels (inquire for prices and details)
- Single Accommodation (available on request, inquire for supplement)
- E-Bike (available on request, inquire for supplement)
Highlights
- Totally unspoiled cycling: olives, sunflowers, vineyards and apricot orchards
- Gorgeous summer climate, soft terracotta colors, 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, mediaeval Montefalco
- Four nights in the fascinating historic city of Spoleto
- Day 1 Day 1 Arrive at Spello
- Day 2 Day 2 Spello to Spoleto 50km/31.5mi
- Day 3 Day 3-5 At Spoleto
- Day 4 Day 6 Spoleto to Marcellano 44km/27.mi
- Day 5 Day 7 At Marcellano
- Day 6 Day 8 Marcellano to Torgiano 42km/26.5mi
- Day 7 Day 9 At Torgiano
- Day 8 Day 10 Torgiano to Spello 43km/27mi
- Day 9 Day 11 Leave Spello

Continental breakfast and 6 evening meals.
Umbria represents Italian home cooking at its best and the region’s cuisine reflects its landlocked location. The distinctive taste of the region’s olive oil and black and white truffles flavor many of the dishes. The origins of many of the dishes derive from thrift, for example, bruschetta comes from toasting stale bread, covering it with olive oil and rubbing it with garlic. Similarly, crostini are thin slices of toast with a smear of pate, usually made from chicken liver, anchovies and capers. Cooked and cured meats also have a fantastic reputation in the region. You will get to try many of these famous and delicious antipasti, which will then be followed by a ‘primo’ (a first course). In Umbria this is usually a pasta dish oozing with flavor. Wild asparagus is popular in the spring and truffles feature more strongly in autumn. Secondi (second course) will then follow, the Umbrian preference is for grilled meats. Rapidly grilled spatchcocked rabbit and guinea fowl remain favorites. Desserts do not feature strongly on the Umbrian menu, cheese is often the post dinner preference and you will find the option to dip them in oil or honey.
Meal times are usually later throughout the day (08:00-10:00 for breakfast; 13:30-15:30 for lunch; 20:00-22:00 for dinner).
Wine also has a strong history in this region. It has been produced in Umbria since Etruscan times, when vines were first planted. Possibly the most unusual wine of the region is the Vernaccia di Cannara, a desert wine which is unlike any other as it is red.
Classification: Self-Guided
Activity Level: 2 (Leisurely/Moderate)
Average daily distance on move on days: 45km (28 miles).
No. of days cycling: 4
Terrain and route: The suggested cycling mainly follows quiet tarmac roads with a few sections on dirt roads. The terrain is mainly undulating but the distances are kept relatively short to give you lots of time to enjoy the scenery.
Vehicle Support: This is a self-guided trip for those who prefer to cycle independently, but with our assistance to take out the stress of the logistics and planning. We arrange your accommodations, provide you with a map and route notes so that you can cycle at your own pace, while your bags are transported from one hotel to the next. A representative will be there to meet you, make sure the bikes are all set up and will be on call throughout the trip should you need.
It is important that you are happy reading maps and following route notes, we make these as accurate as possible and they are regularly checked. Where possible we stick to cycle tracks and quiet roads to make the journeys as pleasant as possible, however, on occasion we have to use busier routes.
As this is a self-guided holiday there is no group and no leader. There maybe others on the same departure date as you, but you will not be organised together. The route notes contain a 24-hour emergency assistance telephone number should you need it and in emergencies, the local representative is normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.
Package Confirmed Dates | Trip Status Trip Status | Price (PP) Excluding Flights | Price (PP) Including Flights | |
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May 1, 2021
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Available |
$2,449.00 |
N/A |
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May 3, 2021
|
Available |
$2,449.00 |
N/A |
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May 5, 2021
|
Available |
$2,449.00 |
N/A |
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May 7, 2021
|
Available |
$2,449.00 |
N/A |
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May 9, 2021
|
Available |
$2,449.00 |
N/A |
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May 11, 2021
|
Available |
$2,449.00 |
N/A |
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May 13, 2021
|
Available |
$2,449.00 |
N/A |
|
May 15, 2021
|
Available |
$2,449.00 |
N/A |
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May 17, 2021
|
Available |
$2,449.00 |
N/A |
|
May 19, 2021
|
Available |
$2,449.00 |
N/A |
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May 21, 2021
|
Available |
$2,449.00 |
N/A |
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May 23, 2021
|
Available |
$2,449.00 |
N/A |
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May 25, 2021
|
Available |
$2,449.00 |
N/A |
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May 27, 2021
|
Available |
$2,449.00 |
N/A |
|
May 29, 2021
|
Available |
$2,449.00 |
N/A |
|
May 31, 2021
|
Available |
$2,449.00 |
N/A |
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June 2, 2021
|
Available |
$2,449.00 |
N/A |
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June 4, 2021
|
Available |
$2,449.00 |
N/A |
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June 6, 2021
|
Available |
$2,449.00 |
N/A |
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June 8, 2021
|
Available |
$2,449.00 |
N/A |
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June 10, 2021
|
Available |
$2,449.00 |
N/A |
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June 12, 2021
|
Available |
$2,449.00 |
N/A |
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June 14, 2021
|
Available |
$2,449.00 |
N/A |
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June 16, 2021
|
Available |
$2,449.00 |
N/A |
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June 18, 2021
|
Available |
$2,449.00 |
N/A |
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June 20, 2021
|
Available |
$2,449.00 |
N/A |
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June 22, 2021
|
Available |
$2,449.00 |
N/A |
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June 24, 2021
|
Available |
$2,449.00 |
N/A |
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June 26, 2021
|
Available |
$2,449.00 |
N/A |
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June 28, 2021
|
Available |
$2,449.00 |
N/A |
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June 30, 2021
|
Available |
$2,449.00 |
N/A |
|
July 2, 2021
|
Available |
$2,449.00 |
N/A |
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July 4, 2021
|
Available |
$2,449.00 |
N/A |
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July 6, 2021
|
Available |
$2,449.00 |
N/A |
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July 8, 2021
|
Available |
$2,449.00 |
N/A |
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July 10, 2021
|
Available |
$2,449.00 |
N/A |
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July 12, 2021
|
Available |
$2,449.00 |
N/A |
|
July 14, 2021
|
Available |
$2,449.00 |
N/A |
|
July 16, 2021
|
Available |
$2,449.00 |
N/A |
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July 18, 2021
|
Available |
$2,449.00 |
N/A |
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July 20, 2021
|
Available |
$2,449.00 |
N/A |
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July 22, 2021
|
Available |
$2,449.00 |
N/A |
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July 24, 2021
|
Available |
$2,449.00 |
N/A |
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July 26, 2021
|
Available |
$2,449.00 |
N/A |
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July 28, 2021
|
Available |
$2,449.00 |
N/A |
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July 30, 2021
|
Available |
$2,449.00 |
N/A |
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August 1, 2021
|
Available |
$2,449.00 |
N/A |
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August 3, 2021
|
Available |
$2,449.00 |
N/A |
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August 5, 2021
|
Available |
$2,449.00 |
N/A |
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August 7, 2021
|
Available |
$2,449.00 |
N/A |
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August 9, 2021
|
Available |
$2,449.00 |
N/A |
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August 11, 2021
|
Available |
$2,449.00 |
N/A |
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August 13, 2021
|
Available |
$2,449.00 |
N/A |
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August 15, 2021
|
Available |
$2,449.00 |
N/A |
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August 17, 2021
|
Available |
$2,449.00 |
N/A |
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August 19, 2021
|
Available |
$2,449.00 |
N/A |
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August 21, 2021
|
Available |
$2,449.00 |
N/A |
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August 23, 2021
|
Available |
$2,449.00 |
N/A |
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August 25, 2021
|
Available |
$2,449.00 |
N/A |
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August 27, 2021
|
Available |
$2,449.00 |
N/A |
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August 29, 2021
|
Available |
$2,449.00 |
N/A |
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August 31, 2021
|
Available |
$2,449.00 |
N/A |
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September 2, 2021
|
Available |
$2,449.00 |
N/A |
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September 4, 2021
|
Available |
$2,449.00 |
N/A |
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September 6, 2021
|
Available |
$2,449.00 |
N/A |
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September 8, 2021
|
Available |
$2,449.00 |
N/A |
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September 10, 2021
|
Available |
$2,449.00 |
N/A |
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September 12, 2021
|
Available |
$2,449.00 |
N/A |
|
September 14, 2021
|
Available |
$2,449.00 |
N/A |
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September 16, 2021
|
Available |
$2,449.00 |
N/A |
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September 18, 2021
|
Available |
$2,449.00 |
N/A |
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September 20, 2021
|
Available |
$2,449.00 |
N/A |
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September 22, 2021
|
Available |
$2,449.00 |
N/A |
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September 24, 2021
|
Available |
$2,449.00 |
N/A |
|
September 26, 2021
|
Available |
$2,449.00 |
N/A |
|
September 28, 2021
|
Available |
$2,449.00 |
N/A |
|
September 30, 2021
|
Available |
$2,449.00 |
N/A |
|
October 2, 2021
|
Available |
$2,449.00 |
N/A |
|
October 4, 2021
|
Available |
$2,449.00 |
N/A |
|
October 6, 2021
|
Available |
$2,449.00 |
N/A |
|
October 8, 2021
|
Available |
$2,449.00 |
N/A |
Mr Inglis
We have now had four holidays with Headwater and this was probably the best. Umbria is still relatively unspoiled and the roads were quiet if not always well surfaced. The holiday took us to several picturesque villages but unfortunately they were often at the top of steep hills so unless you are young and fit be prepared to get off and push occasionally. One of us was happy with four days in Spoleto whereas the other would have preferred more time in any of the other hotels which were clearly better. We took advantage of the extra time in Spoleto by taking the train to Assisi. This seemed to be a better option than visiting it on the final day when we would have been encumbered by bikes. A special mention should be made of the warm welcome and stunning views at he Grand Relais Laurenti
Mr Hodgson
Enjoyable relaxing holiday, with good mix of activites, beautiful scenery,great food and comfortable hotels, highly recommended!
Mr Laxen
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.
Ms Skinner
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
We had a very good time. It was a lovely holiday marred only by the directions being a little bit unreliable.