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

Wine Villages of Umbria Cycling
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- Wine Villages of Umbria Cycling
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, vineyards and poppy strewn meadows with the chance to explore some of the most fascinating towns and historic villages in the region. You'll freewheel 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.
Highlights
Key Information
- 7 nights hotel-to-hotel accommodation in a mix of 3-star and 4-star hotels
- 8 day land only / flight inclusive
- 6 days cycling (2 days optional)
- The suggested cycling is 92% on quiet tarmac roads and 8% 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 and sightseeing.
- Countries visited: Italy
- Countries visited: Italy
What's Included
- 7 nights hotel-to-hotel accommodation in a mix of 3-star and 4-star hotels
- All breakfasts and 2 evening meals
- Management by your local Headwater-appointed agent
- Route directions and maps
- High quality bikes
- Luggage transfers between hotels
What's Not Included
- Optional electric bikes
- Travel insurance
- Single accommodation (available on request - compulsory supplement)
Solo traveller supplements (where only one person is travelling on a departure date)
- Visas or vaccinations
6 Days of Cycling
42 km / 26.1 miles
23 km / 14.3 miles
14 km / 8.7 miles
42 km / 26.1 miles
24 km / 14.9 miles
25 km / 15.5 miles

Itinerary
Spello Assisi
Explore this medieval town, with its cobbled streets resplendent with colourful flower boxes, before dinner.
Meals included: Breakfast
There are lovely views as you cycle along the Teverone Valley to the lively market town of Foligno, with its Romanesque cathedral, evocative Trinci Palace and many museums. Pass the idyllic Fonti di Clitunno, a sacred place of worship to both the Pagans and the Romans, before continuing to stunning Spoleto.
Distance covered: 26mi (42km)
Meals included: Breakfast
There’s time this morning to discover Spoleto’s magnificent architecture, including a Roman arch, 12th century Duomo and 14th century viaduct. It’s a short onward ride via hilltop Colle San Filippo through an undulating landscape of olive groves and vineyards to the tiny hamlet of San Luca at the foot of Montefalco.
Distance covered: 14mi (23km)
Meals included: Breakfast, Dinner
San Luca is ideally placed to discover hilltop Montefalco, the ‘Balcony of Umbria’. Wander round its medieval streets, admire the superb views and enjoy wine tasting in one of the many Sagrantino wineries.
Distance covered: 9mi (14km)
Meals included: Breakfast, Dinner
First stop today is the walled town of Bevagna, home to the 13th century Gothic Palazzo dei Consoli, the golden medieval theatre and Roman temple and baths. Then head past vineyards and the village of Cannara – renowned throughout Italy for its red onion festival! – to the old wine town of Torgiano, famous for its Lungarotti cellars.
Distance covered: 26mi (42km)
Meals included: Breakfast
Lots of options today. Visit the wine and olive oil museum – with tastings – in Torgiano’s centro storico, pedal along the ‘Wine and Art Road’ to Perugia, capital of Umbria and famous for one of Italy’s finest art collections or cycle a circular route to the local ceramics capital, Deruta.
Distance covered: 15mi (24km)
Meals included: Breakfast
Ride along quiet country roads past sunflower and wheat fields, ochre-coloured farmhouses and meadows bordered by fig trees through the Chiasco Valley to Sta Maria degli Angeli. Visit the tiny chapel within the Franciscan basilica, where St Francis used to pray, before continuing to Assisi. There’s plenty of time to explore and visit the beautiful Piazza del Comune, the 13th century Giotto frescoes and of course, the UNESCO recognised basilica.
Distance covered: 16mi (25km)
Meals included: Breakfast
The tour ends after breakfast in Assisi
Meals included: Breakfast
Essential Info
Visa
Italy
Travellers from the UK, US and EU normally do not need a visa to enter Italy. Please note, visa requirements often change and it is your responsibility to obtain any required visas for this trip. Therefore, we recommend that you check with the nearest embassy or consulate of your chosen destination(s), including any countries you may be transiting or transferring through.
Some local governments provide guidance on what visas their citizens need. To help, we’ve gathered a selection of useful links below.
• Australia: www.smartraveller.gov.au/destinations/europe/italy
• Canada: www.travel.gc.ca/destinations/italy
• United Kingdom: www.gov.uk/foreign-travel-advice/italy/entry-requirements
• USA: www.travel.state.gov/content/travel/en/international-travel/International-Travel-Country-Information-Pages/Italy.html
Please note: it is compulsory to carry ID with you at all times in Italy.
Vaccination
Italy
There are no required vaccinations. However, you may want to consider vaccinations for tetanus, rabies and tick-borne encephalitis. Please confirm with your doctor or travel clinic.
Eating and Drinking
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 flavour 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 flavour. Wild asaparagus 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 favourites. 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.
Weather
The dates run from May through to October which will take advantage of the nicest weather of the region. May and October have the lowest average temperature, with highs of around 22 degrees Celcius. In the morning and evenings the temperature may drop to as low as 13 degrees Celcius so it is worth having an extra layer for your top and bottom that you can take off as it warms up. October will also see more chance of rain. From June to September the temperatures will be much higher, rising to 35 degrees Celcius in July and August, with much lower chance of rain. The weather is always variable so this should be used as a guide only.
Is this trip for you?
Cycling Conditions
Classification: Self-Guided
Average daily distance on move on days: 24km (15 miles).
No. of days cycling: 6 (including 2 optional rides)
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 local agent 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.
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 agent is normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.
Families
Self-guided cycling holidays are a perfect option for families as they offer the freedom for you to take your holiday at your own pace. You can stop as and when you want and need, at the cafes and restaurants that suit your family and the sites that interest you. We have suggested the minimum age for this trip is 8yrs as we feel they will be able to ride the bikes we have to offer and complete the route. However our local partner is able to offer child seats for children aged 2-4yrs (max. weight 22 kg, hills will be tricky). These are all subject to availability, and therefore we ask that you enquire about these on booking. Please note due to the size of the bikes and distanced required to cycle, this trip is not appropriate for children aged from 5-7yrs (who are too big for the child seats, but not big enough to ride the children’s bike). As a guide we have suggested that 8yrs is the minimum age for this trip, but as it is self-guided and you will be leading your own family we will ultimately leave this decision up to you. The daily distances are all published in the trip notes along with a description of each days cycling so you have a good idea of what to expect. However, if you have any questions please do not hesitate to contact one of our experts. The principle idea is that these holidays can be as flexible as you like, with logistical support but no group or leader to dictate the daily activities. Please bear in mind the weather when choosing to book, temperatures can be very high in the middle of summer and the child seats provided do not have any shade. We therefore recommend going either earlier or later on in the season if you have young children.
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Would you like to include flights with your booking?
- ATOL protected
- Competitive flight prices
- Full refunds in the event of FCDO cancellations or major disruption at your UK departure airport
- Specialist support to rearrange flights and transfers
- Regional flights available from many UK airports
*Please note any date & price adjustments will be displayed on the next step of booking. You will be able to revert back to booking without flights if the options aren't suitable for you.
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