In the land of gentle hills and valleys, 11th-century frescoes, Renaissance palaces, chamber music, truffles and porcini, is a handsome house in an enviable setting. Its owner is Simon who resides in Monterchi; having lived in Tuscany for 23 years he happily shares his knowledge. Through the gates, up the drive and there is a big ochre house with pale grey shutters on a hill, surveying a fabulous panorama. Step in to find three floors of comfort and light, and an authentic Tuscan décor: arches, beams, balconies, a vast stone fireplace, and elegant sofas on terracotta floors. The kitchen, big, friendly and fun to cook in, leads to dining areas on two sides: one out under the arches, the other in. Bedrooms are large and lovely, with chestnut wardrobes, walnut dressing tables, perhaps an Art Deco bed or a vintage chandelier. Bathrooms are fresh, simple and contemporary. You’re near the hilltowns of Città di Castello and Montone, steeped in medieval history – don’t miss the convent and cloisters of San Franceso. After a day’s hiking or biking in the upper Carpina valley, make a splash in your 50-foot pool.