Enthroned atop an olive-terraced hill on a Chianti vineyard sea, this 14th-century castello encloses a number of comfortable self-catering apartments in two big ancient buildings and a house tucked away in the woods. Acres of landscaped grounds, wonderfully magical, perfectly maintained, have long and spectacular views past statues and cypresses, secret hideaways and jogging trails. There’s a huge pool with snazzy parasols and pergolas, multiple terraces with barbecues, slides, swings, ping pong, volleyball and floodlit tennis, and a hot tub for the lazy. All feels nicely countrified and cared for, with terracotta floors, exposed brickwork, plentiful beams, big sofas piled with cushions, eclectic prints – testament to family travels – and well-stocked kitchens. Casa Colonica can be rented as a single unit but our favourite is the house that hides in the woods; one wall was once part of a cave. Young Guido knows all the secrets and stories: the Castello is his pride and joy. Cycle tours of vineyards beckon, San Gimignano is close, Florence is half an hour. A paradise for families.