A seven-day shape for the stay.
Driving times are typical estimates from Il Palazzino. Use live navigation when setting off.
Day 1
Arrive through Città di Castello.
Collect groceries before the final rural drive, follow the property-specific directions and learn the route between the kitchen, pergola and pool while there is still daylight.
There is no prize for adding a town visit after a flight. Supper at the house or in Monte Santa Maria Tiberina is enough for the first evening.
Day 2
Use Città di Castello as a town, not only a supermarket.
Start with the historic centre, a coffee and the market or everyday streets. The two Alberto Burri collections, Palazzo Albizzini and the former tobacco drying barns, give the town an artistic identity that generic hill-town lists often miss.
Return to the house before the hottest part of the afternoon if the pool is calling. Città di Castello is close enough that a museum visit does not need to consume the whole day.
Day 3
Link Monterchi, Anghiari and Sansepolcro.
These three eastern Tuscan towns form a coherent art-and-streets day. Monterchi holds Piero della Francesca’s Madonna del Parto; Anghiari brings steep stone lanes and the memory of the 1440 battle; Sansepolcro is Piero’s birthplace and holds more of his work.
Do not force equal time into all three. Choose the museum that matters most, keep lunch unhurried and let one town become a shorter walk if the day runs long.
Day 4
Stay mostly at the house, then go up to Monte.
A house day is not a gap in the itinerary. Use the pool, have lunch beneath the pergola and walk the garden when the light is softer. The property was chosen for those spaces, so they deserve more than the hour between two long drives.
Monte Santa Maria Tiberina is about five minutes away by car and works well for an evening walk, a view across the valley and dinner without committing to another major journey.
Day 5
Give Gubbio the larger Umbrian day.
Allow about an hour each way. Gubbio rewards the distance with steep medieval streets, Piazza Grande, Palazzo dei Consoli and the unusual open-basket cable car towards the Basilica of Sant’Ubaldo.
Check the cable car and museum information before leaving. If the weather is poor or the group is tired, swap this day with the flexible final day rather than treating the route as an obligation.
Day 6
Choose one ambitious destination.
Perugia, Assisi, Arezzo and Lake Trasimeno are all realistic, but combining several of them usually produces more driving than understanding. Choose according to the group: Perugia for a layered city, Assisi for medieval art and landscape, Arezzo for a Tuscan centre or the lake for a more open-air day.
Return directly after the chosen place. Adding a second headline destination is usually less rewarding than an evening swim and supper at the house.
Day 7
Keep the final day flexible.
Use it for weather that disrupted an earlier plan, a market, a local festa, a short cycle route or a second visit to the town the group liked most. If everyone wants another pool day, that is also a complete answer.
The current Upper Tiber Valley calendar is useful for adding a local event to the final day.
Sources and live planning links.
Destination and 2026 event information was reviewed on 2 August 2026.
