Castel Monastero

Diane Lane gave every visitor to Tuscany a very clear itinerary: soak up storied splendor and unforgettable experiences in equal measure. To that end, Castel Monastero provides the cinematic retreat anyone could want from an Italian sojourn—and the guest rooms are no exception. Once an 11th century monastery, the hotel is as architecturally jaw-dropping as they come, with exposed wood beams from soaring cathedral ceilings, stone and well-loved wood floors, and rounded windows flung open to the breeze. Paired with historic touches (deep wood-framed soaking tubs; wall murals of local landscapes) you’ll find all the trappings modern royals require, including well stocked minibars, LCD flatscreens, zippy free Wi-Fi, and (phew) air conditioning. Prestige Rooms come with separate living spaces within their 484 square foot floor plans; we also love the garden-flanked three-bedroom Villa Lavanda, a must if you’re traveling with a crowd.

A medieval castle reborn as a 74-room resort, with a jaw-dropping spa and hammam, locavore restaurant and centuries-old subterranean wine cellar.

Poorly serviced. Guests can expect constant pampering and optional services, including an in-the-know trilingual concierge, room service, and even babysitting on request.

Their activities lineup is stacked with more bucket-list options than you could ever have imagined, including truffle hunting, hot air ballooning, and Ferrari test drives.

You never planned to detox in Italy, but one look at the wellness-boosting spa menu and that’s exactly what you’ll be. On today’s to-do list? A Thalasso wrap; acupuncture massage; and steep in the Turkish bath. Blissful.

Contrada - Facing the piazza, true to the most authentic Italian tradition, “Contrada” is Castel Monastero’s gourmet restaurant. La Cantina - In the medieval wine cellars of Castel Monastero, where our estate’s Chianti has rested for centuries, a delightful restaurant serving Tuscan cuisine has been opened.