The Wine Trails of Umbria Cycling

0044 1606 720199

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  • Holiday code
    C07UR
  • Holiday type
    Self-guided cycling
  • Duration
    7 nights
  • Accommodation
    hotel-to-hotel
    and
  • Activity level
  • From $2375per person, tour only
  • NEW FOR 2024  
  • Departure months
    JFMAMJJASOND
  • What your holiday price includes
  • 7 nights hotel-to-hotel accommodation in a mix of and hotels
  • All breakfasts
  • Bike fitting at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Luggage transfers between hotels
  • Optional Upgrades
  • City break add-ons in Rome
  • Room upgrades available
  • Extra nights available
  • Suitable for
  • Solo travellers
  • Couples
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history

Italy: Umbria

The Wine Trails of Umbria Cycling

  • Unspoilt cycling through sun-drenched landscapes: olive groves, boundless vineyards and sunflowers
  • Superb summer climate, soft terracotta colours, panoramic views
  • Assisi, the jewel in the Umbrian crown, gorgeous Spello, historic Spoleto, Etruscan Perugia
  • The medieval wine villages of Montefalco and Torgiano - wine tasting opportunities galore!

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 hilltop villages and beguiling medieval towns.

This 7-night self-guided cycling holiday combines scenic pedalling through olive groves, sunflower fields and lush vineyards with the chance to explore some of the most fascinating towns and historic villages in the region. You'll pedal along the Valle Umbra accompanied by a backdrop of olive grove clad hills topped by panoramic villages 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, baths and mosaics. 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'd stroll and preach to the birds.

Food of the region is rustic and often called 'cucina povera'. Expect to try strangozzi pasta served with black truffles from nearby Norcia or a spicy tomato sauce, followed by simple grilled local meats and then a slice of pecorino cheese washed down with some of the superb Sagrantino di Montefalco wines. 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 0044 1606 720199, use our live webchat or email sales@headwater.com

Cycling information

The cycling is mainly undulating throughout with ascents and descents to and from the hilltop villages, some of which are steep. There is 5% strada bianca on day 4 and 10% on day 5; all other sections / days are on asphalt.




We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Arrive in Spoleto

Discover the town's Roman theatre, 12th century Duomo and impressive 14th century viaduct that bridges the valley with spectacular views.
You stay at the Hotel dei Duchi (breakfast included)

Day 2: Spoleto to Spello (39km/24.2mi)

A gentle ride to start the week's cycling as you pass the idyllic Fonti di Clitunno, a sacred place of worship to both the Pagans and the Romans. Continue through the valley past sunflower fields and vineyards, with a stunning backdrop of the Teverone hills, before continuing to the medieval town of Spello, with its cobbled streets resplendent with colourful flower boxes.
You stay at the Albergo il Cacciatore (breakfast included)

Day 3: At Spello - loop ride to Bevagna and Montefalco (48km/29.8mi)

Pedal along the Topino river to your first stop of the day, the walled town of Bevagna, home to the 13th century Gothic Palazzo dei Consoli, the golden medieval theatre and Roman temple and baths. Then follow the famous wine route, the 'Strada del Sagrantino' uphill to the wine village of Montefalco, known as the balcony of Umbria for its superb panorama. A downhill whizz takes you back on the road to Spello.
You stay at the Albergo il Cacciatore (breakfast included)

Day 4: Spello to Torgiano (30km/18.6mi)

Head past olive groves to the medieval, walled village of Cannara, renowned throughout Italy for its red onion festival! There's the option to detour to the medieval hilltop town of Bettona, known as the 'Etruscan balcony' for its superb views and Etruscan origins. End the day in the old wine town of Torgiano, famous for its Lungarotti cellars.
You stay at the Hotel Al Grappolo d'Oro (breakfast included)

Day 5: At Torgiano - loop ride to Deruta (36km/22.4mi)

Lots of options today. Visit the wine and olive oil museum - with tastings - in Torgiano's centro storico, cycle a circular route to the local ceramics capital of Deruta, or take a taxi to Perugia, capital of Umbria and famous for one of Italy's finest art collections.
You stay at the Hotel Al Grappolo d'Oro (breakfast included)

Day 6: Torgiano to Assisi 34km/21mi (34km/21.1mi)

Cycle to the sleepy village of Brufa, with its quirky contemporary sculptures perched high on the hilltop, then continue through vineyards, olive groves and wheat fields, before a final climb up to majestic Assisi.
You stay at the Hotel Porta Nuova (breakfast included)

Day 7: At Assisi - loop ride to Sta Maria degli Angeli or Collepino (15km/9.3mi or 30km/18.6mi)

There's so much to explore in Assisi with its beautiful Piazza del Comune, the 13th century Giotto frescoes and of course, the UNESCO recognised basilica. It's a short ride to Sta Maria degli Angeli to visit its impressive 16th century basilica, or walk up through woods to the Eremo delle Carceri - St Francis' hermitage - on the flanks of Monte Subasio. Die hard cyclists can take the challenging climb along the Via degli Ulivi to the hilltop, pink hued village of Collepino, for superb views over the entire valley.
You stay at the Hotel Porta Nuova (breakfast included)

Day 8: Leave Assisi


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 0044 1606 720199, use our live webchat or email sales@headwater.com


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

Hotel dei Duchi, Spoleto

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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.


Extra nights: Please contact us for details.


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

Albergo il Cacciatore, Spello

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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.


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

Hotel Al Grappolo d’Oro, Torgiano

Swimming Pool IconHair dryer icon NEARBY:

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 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 make it a lovely place to relax.


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

Hotel Porta Nuova, Assisi

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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.


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.


Read customer reviews on Tripadvisor.

Hotel Canada Roma, Rome

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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.


Room upgrades: Deluxe and junior suite
Deluxe rooms are larger with a more stately decor.
Junior suites have a separate living room.

Travel

Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.

Reviews

Here at Headwater we thrive on feedback and pride ourselves on our excellent customer service. Below is a small selection of reviews we've received from our satisfied customers.


03/01/2024

Attentive to detail, clear and helpful, always a pleasure to deal with them.


27/10/2023

Great advice. Worth calling to hear about holidays you might not have thought of. Megan really listened to what we were after. Can’t wait to visit Malta and Gozo next year!


Petra Hirst, 08/08/2023

Headwater is always excellent - that's why I go back to them every time I do an activity holiday. The advisors are professional, helpful, friendly and very efficient and I am sure the holiday won't let me down.


26/05/2023

very good service from all concerned in Croatia.

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.

This 7 night self-guided cycling holiday includes:

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

All breakfasts

Bike fitting at the start of your holiday

Headwater navigation app for your smartphone

Bike hire

Luggage transfers between hotels


How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

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19th Apr 2025 US$2585 Tour only: US$2585 Check availability
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20th Apr 2025 US$2585 Tour only: US$2585 Check availability
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1st May 2025 US$2525 Tour only: US$2525 Check availability
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1st Oct 2025 US$2585 Tour only: US$2585 Check availability
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27th Oct 2025 US$2585 Tour only: US$2585 Check availability
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28th Oct 2025 US$2585 Tour only: US$2585 Check availability
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29th Oct 2025 US$2585 Tour only: US$2585 Check availability
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30th Oct 2025 US$2585 Tour only: US$2585 Check availability
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31st Oct 2025 US$2585 Tour only: US$2585 Check availability
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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

Solo travellers
Please call for details and prices

Children
Please contact us for child prices.

Holiday type
Self-guided cycling Managed locally by Headwater appointed agent.

Departures
Daily from 29th Apr 2024 to 31st Oct 2025, for 7 nights. All dates are subject to availability, please contact us to check.

Meals
All breakfasts

Tailor-made travel

Tour only

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.

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