Benchmarked strictly across TripTiming's 5 empirical pillars: Crowds, Weather, Vibes, Prices, and Safety.
Oaxaca emerges as the optimal May destination with an overall TripTiming Index of 66/100 vs 62/100 for Mexico City (+4 point advantage). Oaxaca experiences substantially lower visitor footfall and shorter landmark queues (moderate footfall vs heavy visitor congestion in Mexico City). Urban navigability is also slightly smoother and more predictable. Travelers also benefit from lower accommodation costs (~$112/night vs ~$201/night in Mexico City, saving ~$623 over a week). While Mexico City retains an edge in Weather Comfort (79/100 vs 68/100), Oaxaca's commanding performance in Space & Crowds secures the overall May recommendation.