Monastero di Cortona Hotel & Spa

All of Cortona’s best hotels are located inside landmark buildings — palaces in town, country estates set amid vineyards — and the Monastero di Cortona Hotel & Spa is no exception. Indeed, this 15th-century monastery, with its gorgeous original frescoes, high vaulted ceilings, and breathtaking hilltop vantage point, may be the most impressive of them all. The imposing stone building was thoughtfully restored and transformed into a luxury boutique hotel in 2019, and it remains one of the most elegant lodgings in this corner of Tuscany.

Rooms and suites, almost entirely outfitted in shades of cream and white, are all unique. Attic rooms have wooden flooring, quaint beamed ceilings, marble bathrooms, and views of the monastery’s cloisters, while larger suites feature travertine tile floors and French doors leading onto private terraces. The friars’ former garden is now home to a wide, sun-drenched terrace with a small swimming pool and views over the surrounding landscapes; the spa’s luminous indoor pool, framed by old stone archways, is even more striking. The house negroni — a custom blend inspired by the original, a proudly Tuscan invention — is served on the rooftop garden with views over Cortona’s rooftops and the hills beyond.