Benchmarked strictly across TripTiming's 5 empirical pillars: Crowds, Weather, Vibes, Prices, and Safety.
Mykonos emerges as the optimal May destination with an overall TripTiming Index of 72/100 vs 70/100 for Santorini (+2 point advantage). Mykonos experiences more manageable visitor density and shorter landmark queues (carrying capacity score 50/100 vs 43/100 in Santorini). This is reinforced by lower lodging rates (~$377/night vs ~$401/night, saving ~$168 over 7 nights).