
Castiglion del Bosco
Villa Agresto
Sleeps 12 · 6 bedrooms
TuscanySub-region
Italy's green heart, directly east of Tuscany — the same hill towns and cuisine, with far fewer crowds.
On Umbria
Umbria is not Tuscany, and it does not want to be: the green, land-locked neighbour over the southern border, quieter and less visited, with hill towns that would be headline acts anywhere else in Italy. For a villa week based in the south of our collection, Umbria is the second country of the trip, close enough that the border is a line you cross for lunch.
We keep no houses in Umbria itself. What we offer instead is honest proximity: from the Castiglion del Bosco estate in the Val d'Orcia, the border country around Città della Pieve is about an hour's drive, Lake Trasimeno a little over, Orvieto a long but worthwhile morning. Guests who want Umbria at the centre of the week rather than its edge should tell us; for everyone else, one or two Umbrian days deepen a Tuscan week considerably.
Three day trips earn their drive. Orvieto, for the cathedral facade and the white wine, pairs the most dramatic hill-town site in central Italy with an easy, flat old town once the funicular has lifted you up. Città della Pieve, Perugino's home town, is the closest and quietest, all rose-pink brick and almost no tourists. And Lake Trasimeno gives a swimming-and-fish-lunch day when the inland heat peaks, with Isola Maggiore reached by a short ferry from Tuoro or Passignano.
When to come
May, June, September and October, the same shoulder logic as the Val d'Orcia. Umbrian hill towns hold their own in high summer better than crowded Tuscany, which makes July and August day trips surprisingly pleasant.
Towns worth knowing
Best for
Practicalities
From the Val d'Orcia houses, count about an hour to Città della Pieve, a little more to Trasimeno, and around ninety minutes to Orvieto or Assisi. Umbrian roads are good and empty by Tuscan standards.
Frequently asked
None of our houses sit inside Umbria itself — these are the ones we would stay in to spend days here.

Castiglion del Bosco
Sleeps 12 · 6 bedrooms

Castiglion del Bosco
Sleeps 8 · 4 bedrooms

Castiglion del Bosco
Sleeps 10 · 5 bedrooms

Castiglion del Bosco
Sleeps 6 · 3 bedrooms
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