Among the oldest inhabited estates in Tuscany, the castello at Casole d'Elsa traces its documented history to the tenth century, when the fortified complex served as a seat of Sienese ecclesiastical power. Castello di Casole, A Belmond Hotel, was carved from that accumulated fabric — medieval watchtowers, a Romanesque chapel, and a later Renaissance villa ranged across a 4,200-acre estate — and converted into a 39-suite property that opened in 2012. The aerial view confirms how little the conversion imposed on the compound: the honey-coloured pietra serena walls and terracotta-tiled rooflines remain exactly as centuries of Tuscan agriculture shaped them, Italian cypress punctuating the forecourt in the manner unchanged since at least the eighteenth century. Inside, the interiors maintain the same discipline of restraint. Bedroom floors are original terracotta cotto laid in herringbone patterns, their warm russet tones grounding baroque-scroll walnut headboards and wrought-iron candle sconces that carry the feeling of a private Sienese palazzo rather than a managed hotel room. Exposed rubble-stone walls in some accommodations push the medieval substrate to the surface. The restaurant unfolds beneath a sequence of brick barrel arches washed in deep burnt sienna, with polychrome encaustic tile floors and cascading Murano glass chandeliers introducing a deliberate note of theatricality. From the infinity pool, the Val d'Elsa rolls away toward Monteriggioni in a view that the estate's original builders understood perfectly well.

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Immersed within rolling hills of breathtaking Tuscan nature, Castello di Casole, A Belmond Hotel, is an authentic farm estate that invites guests to live from the land. Approached along a winding road lined with statuesque cypress trees, the restored medieval castle offers a sanctuary in which to disconnect from modern-day living. Vineyard walks, cycling trails, stargazing and sustainable cooking classes are among the activities. The magnificent vaulted spa, set in the former wine cellar, offers grape-inspired treatments. A serene infinity pool affords spellbinding vistas of the undulating hills. Enchanting rooms and suites boast exposed brickwork and open fireplaces. Organic produce, oil and wine from the estate form the basis of Casole’s menus. Late-night cocktails are enjoyed at glamorous Bar Visconti.