On a vast Tuscan estate near Casole d'Elsa, Castello di Casole rises from vineyards, cypress lanes and wooded hills with the assurance of a restored medieval village. The rooms and suites draw on stone walls, timber beams, terracotta, velvet and marble, giving the castle's history a warmer, more inhabitable polish. Days move from the pool with its long country views to Essere Spa, estate walks, wine, olive oil, cooking, tennis and generous Italian dining. It feels expansive yet private, a place where Tuscany is not styled for effect so much as allowed to unfold with uncommon ease.