Journey · 8 days · 3 homes
Umbria & southern Tuscany
in eight days
Two nights near Orvieto, three between Gubbio and Perugia, three in the Val d'Orcia and around Cortona.
The idea
The green heart of Italy and the hills of southern Tuscany
Umbria is Tuscany's quieter neighbour: hill towns of pink stone, Franciscan sanctuaries, truffles and Sagrantino. The journey ends across the border, in the Val d'Orcia and in Cortona.
- 1Orvieto 2 nights
- 2Gubbio & Perugia 3 nights
- 3Val d'Orcia & Cortona 3 nights
Day by day
8 days, 3 homes
For every stop: what to see and where to go, the dishes to try and where to eat them. Below, two or three of our homes in the area, with live rates for your nights.
Stop 1 · 2 nightsDays 1 – 2
Orvieto, on its rock
Orvieto stands on a block of volcanic rock above the vineyards of its white wine. Below the town runs a second city of caves and wells dug over three thousand years.
What to see & where to go
- The Duomo and Signorelli's frescoes in the Chapel of San Brizio
- Orvieto Underground and the Well of St Patrick
- The Etruscan necropolis of the Crocifisso del Tufo
- Civita di Bagnoregio, the 'dying town' reached by a footbridge
- Lake Bolsena
- A tasting of Orvieto Classico in the hills
What to eat
- Umbrichelli with black truffle
- Porchetta, roast pork with wild fennel
- Lumachelle, the small savoury buns of Orvieto
- Orvieto Classico, the white wine of the rock
Where to eat
- Trattoria del Moro Aronne, for Umbrian home cooking
- I Sette Consoli, with a garden facing the Duomo
- Porchetta from any stall on market day
Where you sleep
La ChiusettaOrvieto, below the cliff
Country house in the vineyards under the town, pool.Why stay hereA 19th-century country house among the Umbrian hills, a few minutes from Orvieto.See the home
Country house in the vineyards under the town, pool.Why stay hereA 19th-century country house among the Umbrian hills, a few minutes from Orvieto.See the home
Borgo San FaustinoOrvieto hills
Restored hamlet in the countryside, ten minutes from the centre.Why stay hereHistoric farmhouses on a hillside with open views over Umbria, spa and outdoor pool.See the home
Restored hamlet in the countryside, ten minutes from the centre.Why stay hereHistoric farmhouses on a hillside with open views over Umbria, spa and outdoor pool.See the home
EremitoParrano
Hermitage-style retreat in the woods, single cells, silence at dinner: for those who want it.Why stay hereA retreat inside a 3,000-hectare nature reserve, with vegetarian cooking and a spa.See the home
Hermitage-style retreat in the woods, single cells, silence at dinner: for those who want it.Why stay hereA retreat inside a 3,000-hectare nature reserve, with vegetarian cooking and a spa.See the home
Stop 2 · 3 nightsDays 3 – 5
Gubbio, Perugia and Assisi
The medieval heart of Umbria: Gubbio's grey stone palazzi, Perugia's Etruscan and Renaissance centre, and Assisi, the town of St Francis.
What to see & where to go
- The Basilica of St Francis in Assisi and Giotto's frescoes
- Gubbio's Palazzo dei Consoli and the Piazza Grande
- The Galleria Nazionale dell'Umbria in Perugia
- Spello and its flower-filled lanes
- Montefalco and the Sagrantino wineries
- Deruta for hand-painted ceramics
What to eat
- Torta al testo, the griddle flatbread filled with greens or ham
- Truffle: white in Gubbio in autumn, black from Norcia
- Sagrantino di Montefalco
- Perugia chocolate and lentils from Castelluccio
Where to eat
- Pasticceria Sandri in Perugia, open since 1860
- Truffle dishes in any osteria in Gubbio in season
- A Sagrantino tasting and lunch at a Montefalco estate
Where you sleep
Castello di PetroiaGubbio
12th-century castle on its own hill, where Federico da Montefeltro was born; pool and restaurant.Why stay hereA medieval castle near Gubbio with its original interiors, a pool in the gardens and a restaurant.See the home
12th-century castle on its own hill, where Federico da Montefeltro was born; pool and restaurant.Why stay hereA medieval castle near Gubbio with its original interiors, a pool in the gardens and a restaurant.See the home
Castello di BaccarescaGubbio
Small castle among the woods, a few kilometres from Petroia.Why stay hereA 14th-century castle overlooking the Umbrian valley near Gubbio.See the home
Small castle among the woods, a few kilometres from Petroia.Why stay hereA 14th-century castle overlooking the Umbrian valley near Gubbio.See the home
Relais dell'OlmoPerugia
Country relais just outside Perugia, easy for all three towns.Why stay hereA country house 5 km from Perugia, convenient for Assisi, Spello and Montefalco.See the home
Country relais just outside Perugia, easy for all three towns.Why stay hereA country house 5 km from Perugia, convenient for Assisi, Spello and Montefalco.See the home
Stop 3 · 3 nightsDays 6 – 8
Val d'Orcia and Cortona
The last stop crosses into Tuscany: the Val d'Orcia with its cypress lanes and Renaissance towns, and Cortona, the Etruscan hill town above the Valdichiana.
What to see & where to go
- Pienza and its Piazza Pio II
- Montepulciano and its underground cellars
- Cortona's Etruscan museum and the Fra Angelico Annunciation
- Bagno Vignoni and its thermal square
- The Abbey of Sant'Antimo
- Chiusi and its Etruscan tombs
What to eat
- Pici all'aglione, hand-rolled pasta with garlic and tomato
- Chianina beef from the Valdichiana
- Pecorino di Pienza
- Vino Nobile di Montepulciano and Cortona Syrah
Where to eat
- Osteria La Porta in Monticchiello
- Osteria Acquacheta in Montepulciano
- Pici with garlic sauce in any trattoria in Cortona
Where you sleep
Palazzo Pio IIISarteano
Renaissance palazzo in a hill town on the edge of the Val d'Orcia.Why stay hereA historic palazzo with a small spa, perfectly placed between the Val d'Orcia and the thermal springs of southern Tuscany.See the home
Renaissance palazzo in a hill town on the edge of the Val d'Orcia.Why stay hereA historic palazzo with a small spa, perfectly placed between the Val d'Orcia and the thermal springs of southern Tuscany.See the home
Fattoria SvetoniMontepulciano
Wine estate with rooms in the old farmhouse, Vino Nobile made on site.Why stay hereA wine resort among the Sangiovese vineyards of Montepulciano.See the home
Wine estate with rooms in the old farmhouse, Vino Nobile made on site.Why stay hereA wine resort among the Sangiovese vineyards of Montepulciano.See the home
Il FalconiereCortona
17th-century villa and wine estate below Cortona, restaurant and spa.Why stay hereA 17th-century villa near Cortona with a Michelin-starred restaurant, spa and pool.See the home
17th-century villa and wine estate below Cortona, restaurant and spa.Why stay hereA 17th-century villa near Cortona with a Michelin-starred restaurant, spa and pool.See the home
Plan it yourself, with help
Ask our assistant
This itinerary is a starting point. Tell the assistant your dates and constraints and it re-plans the stops on our homes, then checks the rooms.
- Can we add two nights in Rome at the start?
- Which of these castles works with a stroller?
- Check the three homes for arrival on May 18
It answers in English, knows every home in our collection and can check live rates and book for you, in the chat. It does not know your budget or dates until you tell it.
