Benchmarked strictly across TripTiming's 5 empirical pillars: Crowds, Weather, Vibes, Prices, and Safety.
Mykonos emerges as the optimal May choice with an index of 73/100 vs 72/100 for Santorini. While both cities offer viable travel windows, Mykonos benefits from more favorable lodging value (standard room rates) and manageable carrying capacity ratios.