There are those who rank this venerable luxe classic, now owned by Orient-Express, as the ultimate Grand Tour hotel. A former monastery, in part designed by Michelangelo, the 46-room property surveys the city from a lofty perch up in Fiesole, a villa-dotted hilltop village that has long been the Florentine aristo's favored refuge from the summer heat. It's San Michele's romantic setting that makes it such a perennial favourite—especially for weddings and honeymoons—with lemon trees on flower-edged terraces, a heated outdoor pool, and the elegant Loggia restaurant, which frames Florence and the Arno valley from an arcaded terrace. The rooms vary in size and aspect: Some are in the main building, others (such as the romantic Conservatory suite) hidden in the grounds. All are done out in an antique style that never feels gloomy thanks to summery magnolia-hued walls and opulent fabrics. Service is impeccable, and chef Attilio di Fabrizio's thrice-weekly Italian cooking classes are well worth signing up for. Despite the high price to stay here, expect to be charged for every little thing, except the shuttle bus that takes guests into central Florence in around 20 minutes.—Lee Marshall