Grand houses proverbially have grand souls, but the striking thing about Villa Gastel, on the shores of Italy’s Lake Como, is its mixture of the fabulous and the familial. The immense villa was a Benedictine convent, dating back to the 12th ­century, before it became the property of one of northern Italy’s most important families, the ­Visconti di Modrone. During the second part of the 20th century, the legendary director Luchino Visconti hosted Maria Callas, Helmut Berger, and Coco Chanel, among many others, at Villa Gastel. But for all its aesthetic charm, the house also exudes the homey warmth that comes from being loved by many generations.

“It has historically been a house of great art and elegance, but also of parents and children—the country life of a big family,” says the present chatelaine, Anna Gastel, who is the niece of the director. “Uncle Luchino grew up here and always adored the place. He enjoyed the huge dinner tables of us nieces and nephews, and sometimes put private family jokes into his movies, just to make us laugh.”