Benchmarked strictly across TripTiming's 5 empirical pillars: Crowds, Weather, Vibes, Prices, and Safety.
Milan emerges as the optimal May destination with an overall TripTiming Index of 57/100 vs 50/100 for Florence (+7 point advantage). Milan experiences substantially lower visitor footfall and shorter landmark queues (heavy visitor congestion vs peak seasonal crowding in Florence). This is reinforced by lower lodging rates (~$319/night vs ~$378/night, saving ~$413 over 7 nights). While Florence retains an edge in Weather Comfort (83/100 vs 57/100), Milan's commanding performance in Space & Crowds secures the overall May recommendation.