Castello di Casole

Set on a ridge above the Tuscan countryside near Siena, Castello di Casole centres on a castle first built in 998, its walls raised on ground farmed since Etruscan times. The estate spans vineyards and olive groves worked by the hotel itself, producing a private-label wine and an olive oil bottled in limited runs each year. Thirty-nine rooms and suites and two villas are spread through the castle and its outbuildings; the five Limonaia Suites, once used to overwinter lemon trees, keep their garden terraces and open onto direct light. An Etruscan amphitheatre, one of the oldest structures on the grounds, now hosts open-air dinners and summer film screenings. You can walk from the heated infinity pool along footpaths that cross the estate's game reserve, where deer, hare and pheasant are common sights. Tosca, the main restaurant, serves Tuscan dishes built on ingredients grown on site, while Bar Visconti keeps its marble counters and frescoed walls beneath a poolside terrace. A wine cellar sits below the courtyard, stocked chiefly with regional labels. Truffle hunts, cooking classes and guided rides through the vineyards fill the activity list, alongside tennis courts run with a private coaching partner. Check-in runs from 3pm. Florence sits 67 km away by road, making the castle a workable base for day trips into the city or the hill towns nearby.