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Villages and castles in the Upper Tiber Valley

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Villages and castles in the Upper Tiber Valley

Discover the castles between Umbria and Tuscany, following the river Tiber and its history

This moderately difficult tour develops along the Upper Tiber Valley in a setting that perfectly combines the beauty of the landscape and the historical and cultural riches of this fascinating borderland. The starting point is just outside the walls of Città di Castello, in Viale Nazario Sauro. From here we’ll cycle towards the river Tiber, cross the bridge and then move towards the highest and most magnificent point on our itinerary, Monte Santa Maria Tiberina. After a long stretch on a gentle slope, the real climb will begin: 4 km on slopes with a gradient of around 6-7% between majestic chestnut woods and breath-taking landscapes that flow through the valleys of Umbria and Tuscany. Once the climb is over, we will soon reach the beautiful medieval village of Santa Maria Tiberina where we will stop to appreciate the splendid panorama again – which on particularly clear days extends to the Apuan Alps and the Gran Sasso d’Abruzzo – and to visit the 16th-century castle and the graceful church of Santa Maria inside its walls. Our itinerary will continue, taking on two more short climbs on verdant hills immersed in the unspoilt nature of these areas straddling Umbria and Tuscany, until we reach the village of Lippiano. Afterwards we will cycle in the direction of Tuscany and stop in Monterchi, the birthplace of the painter Piero della Francesca. After looking around the village we will return to our starting point, Città di Castello. At this point we can’t miss out on seeing the many art works and monuments that make it the pearl of the Upper Tiber Valley. Choose to spend a day immersed in nature and culture: our guides will accompany you and reveal every little secret hidden in these magical places. Book now, we are looking forward to having you with us on the tour.

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  1. 1

    h. 09:30
  2. 2
    first part of the trail

    h. 09:40
  3. 3
    lunch break

    h. 13:00
  4. 4
    second part of the trail

    h. 14:00

Recommended clothing

  • For this activity we recommend comfortable clothing that does not restrict your freedom of movement.
  • Bring a windcheater/anorak with you, even if the activity takes place in the summer months.
  • We recommend wearing the right footwear for the type of bike you are going to use.
  • We strongly recommend the use of a crash helmet suitable for biking.

We also recommend you bring:

  • A comfortable backpack suitable for cycling/walking
  • A warm sweater, such as a technical sports shir, for sudden drops in temperature
  • A change of clothes (especially socks) in case of sudden rain
  • Hat with a sun visor
  • Warm hat
  • Gloves
  • Sunscreen


  • Expert guide
  • Mechanical assistance for repairs in case of punctures, problems with brakes or other malfunctions that can be dealt with on the spot.
  • In most cases a car will be on hand to provide any complex assistance or to keep drinks and food chilled.

Not included

Bicycles and related accessories are not included in this itinerary.

If you wish, you can choose bike hire from amongst our additional options. We will provide you with the bike that’s best suited to the type of route, taking your preferences into consideration, including helmets, pedaling accessories and spare parts for ordinary repairs. We have various types of bikes available, including e-bikes.


The activity will last about 7 hours, including small stops. However, the duration may vary depending on the pace of the group and the need to take fewer or more breaks.


  • Italian
  • English


You can enjoy this experience throughout the year.


This activity is also open to children provided they are accompanied by their parents.

Pet policy

We are sorry but no pets will be allowed to accompany you in this activity.


To do this activity it is essential to have a good level of physical fitness and to be in good health.

Additional information

This activity includes a lunch break, so we advise you to bring a packed lunch or to select the option ‘packed lunch’ so that we can provide it for you. Don’t forget to tell us about any allergies, intolerances or other special dietary needs: we will be happy to adapt your lunch to your needs.


  • This activity can only be undertaken in favourable weather conditions, which will be evaluated by our partner and confirmed 48 hours in advance. In case of poor weather conditions we will immediately contact you and propose an alternative activity or a refund of the price paid.
  • This activity is subject to our operators’ availability. We have a large selection of collaborators capable of leading this activity, but if on the day you selected we do not have operators availabile, we will immediately, or in any case within 48 hours of booking, suggest an alternative activity you might wish to do or the choice of receiving a full refund of the price paid.
  • The times shown in the program are indicative and may vary according to your requests or those of the other participants in the group. These are always and in any case previously agreed with our staff or with the guide.



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Always communicate through Exploring Umbria to ensure you receive the best bespoke service to suits your requirements. In order to protect your payments, never transfer money via channels outside the Exploring Umbria website.

Cancellation policy

If you cancel the reservation for this activity up to 24 hours before the event we will refund you 100% of the price.

Where you can do this activity

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