022025 · Italy
A Long Weekend on an Umbrian Estate
A thousand-year-old castle, a truffle hunt, and a sunset over Cortona.
Duration
Four days, three riding
Party
Two
Base
Castle estate, Niccone Valley
Shape
Long weekend
—The Trip
01Thursday
Arrival
Private transfer from Pisa. Dinner in the suite or the restaurant, depending on when the plane lands.
02Friday
Ride to the vineyard
A morning ride finishing at a working vineyard for a picnic lunch and tasting. A ninety-minute massage in-room, then up to a hilltop town at six for the sunset and dinner in a thirteenth-century palace.
03Saturday
Ride and truffle hunt
Morning on farm tracks and singletrack through the estate. Lunch on the property, then a guided truffle hunt in a region built on them. Dinner for two over the valley with music.
04Sunday
Last ride
Two hours out before checkout, the bathhouse held open for showers, lunch, and the transfer to the airport.
Long weekends are the hardest trips to plan and the easiest to love.