Four Seasons Hotel Milano occupies a former 15th-century convent in the city’s fashion district, creating a rare pocket of calm between Via Montenapoleone and Via della Spiga. The cloistered courtyard and garden give the hotel its strongest character, while the renovated rooms and suites bring a more contemporary Milanese elegance to the historic structure. Dining and drinks unfold around the courtyard, and the spa sits beneath vaulted brick ceilings. The property feels closely tied to Milan’s design and shopping culture, but with a quieter, more secluded rhythm.