Originally built in the 11th century, Podere La Gloria has aged beautifully, like a fine Chianti wine. It’s a light-filled hilltop hideaway conjured out of a medieval tower and an old barn, and blanketed in Boston ivy, which was sensitively restored in 2023 in a top-to-toe makeover by owners Jane and Steven Collins (she is an antiques dealer, he a hotelier), who also run Henry’s Townhouse in Marylebone and Cotswold estate Temple Guiting. Their taste is exquisite. Clean, elegant interiors embody Italian quiet luxury, the earthy palette injected with fun points of focus thanks to abstract art by Peter Haigh, vintage Giotto Stopino furniture and statement seating by Pierre Paulin. Light, open living spaces foster connections, designed for eating, drinking and hanging out, from laid-back breakfasts and espressos in the well-equipped kitchen that opens up onto the garden, to chef-prepared feasts beneath the vaulted ceiling of the dining room, with its great wooden table for 16 – the perfect place to fill with your favourite people.  There are eight fresh-faced, elegant bedrooms. Some have living spaces with fireplaces, some open onto gardens, two have free-standing bathtubs, and all but one have en-suite bathrooms kitted out with Dyson hairdryers, Frette bathrobes and bathroom products from Florentine institution Santa Maria Novella, the world’s oldest pharmacy. A separate studio by the pool is perfect for extra guests or round-the-clock staff. At every turn – from bedroom windows, verandas, various terraces, gardens – are sensational views of the green patchwork hills stretching out below. Outside there’s an outdoor kitchen (complete with Fontana pizza oven), dining areas, seating nooks for beating a retreat from the crew, and the most beautiful hand-tiled infinity pool, lined with parasols, that feels suspended mid-air, high above the Tuscan landscape.