Val d'Orcia and Umbria on Foot

Five nights on foot through southern Tuscany and into Umbria, with a guide, the routes mapped and the bags carried ahead. Two nights on a Brunello estate in the Val d'Orcia with Italy's only private golf club, three in a castle on the Umbrian border where purebred Spanish horses are trained in classical dressage, and Florence at the end.

Length: Five nights
Pace: Two stays
Style: Walking, food and wine, countryside
Route: The Val d'Orcia to Cortona and the Umbrian hills

The Val d'OrciaTwo nights
Cortona and the Umbrian hillsThree nights

An infinity pool with parasols and loungers below the stone borgo at sunset. — Photo: Castiglion del Bosco, A Rosewood Hotel

Days 1 to 3 · two nights

The Val d'Orcia

Collected and driven into the Val d'Orcia. A walk across the valley to lunch on a farm, and a second from Montepulciano to Monticchiello for lunch. Back on the estate, a truffle hunt followed by Brunello, a tasting at the Castiglion del Bosco winery, or a hands-on class at La Canonica Cooking School; golfers can play The Club, open only to hotel guests and members.

Where you stay

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco is a private estate of 5,000 acres in the Val d'Orcia, centred on a 900-year-old borgo, and one of the historic producers of Brunello di Montalcino. There are 42 suites and 11 restored farmhouse villas, Osteria La Canonica within the borgo, and Italy's only private golf club.

Old stone buildings of a hermitage stepped into a wooded hillside.

Days 3 to 6 · three nights

Cortona and the Umbrian hills

On foot to the Celle hermitage of St Francis and on into Cortona, for a guided walk through the Etruscan town and a MICHELIN-starred culinary experience at Il Falconiere. Then over the border into Umbria for a crostata lesson and lunch in a friend's garden. At Reschio, a ride through the estate's nature reserve or a lesson in the Teatro Equestre on its Spanish horses, and one of the week's workshops in embroidery, ceramics or bookbinding, or a day with the makers of Perugia and Deruta: the historic hand looms of the Giuditta Brozzetti workshop, the Moretti Caselli stained-glass studio and the maiolica workshops of Deruta. A last walk through the countryside to Montone, and a drive to Florence.

Where you stay

Hotel Castello di Reschio

Reschio is a private estate of 3,700 acres in the Umbrian hills, and its hotel is a castle built in 1050, restored by the Bolza family. Two restaurants cook from the gardens, and the Bathhouse in the old wine cellars sits alongside riding, rowing on the lake and walks in ancient woods.

Arranged on request

The Club at Castiglion del Bosco

Italy's only private golf club, open to hotel guests and members.

Truffles and Brunello

A truffle hunt in the countryside of the estate, then Brunello di Montalcino from its own winery.

The Teatro Equestre at Reschio

Lessons or guided rides on the estate's purebred Spanish horses, bred from the stud Count Antonio Bolza founded; its trainer, Antonello Radicchi, guides experienced riders towards classical dressage, and weekly demonstrations are open to guests.

Reschio's weekly workshops

Embroidery, ceramics, bookbinding and herbalism, offered each week on the estate.

A day with Umbria's makers

The historic hand looms of the Giuditta Brozzetti workshop and the Moretti Caselli stained-glass studio in Perugia, then the maiolica workshops of Deruta, can be arranged as one day from Reschio.

Subject to availability.

Ways to make it yours

Two more nights in Florence at Dimora Ghirlandaio.
A day in Montefalco, walking from the cellar out into the Sagrantino vineyards above the Spoleto plain for a picnic lunch, with a guided tour of the cellar.
A day on the Via Francigena pilgrim path from Castiglion del Bosco, three to seven hours on foot.

This is a sample. The hotels, the pace and the order are where we start, not where we finish: every journey is designed around the people taking it.

Made around you

Most travel is bought. This is designed.

Before anything is booked, we talk: who is travelling, how you like to spend a morning, and the hotel preferences below the obvious, from the kind of bath you like to the time you wake and how much daylight you need in a room. You see options where options matter and clean recommendations where they don't.

The same person remains your point of contact from the first reply to the trip after next. No handovers. No team.