On the warmest days of the month, the temperature may reach 18.5°C/65.3°F. The day lasts approximately 11 hours. The sunshine lasts about 5 hours. Humidity reaches 68%, while the average speed of the wind is around 24 kph (15mph).
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May in Santorini: The weather in May is consistently sunny and warm. May is one of the best months of the year to visit Santorini when the temperatures are high and the chance of rain is low. Santorini hotels have availability and great rates!
Shorts are acceptable on the beach or when going from the beach to the shops near-by. If you plan to take a ferry between the islands, shorts are a good option if you travel by day (opt for a pair of long pants though if you travel by night).
Diaporos is never windy—unlike most of GreeceIt is an ideal destination not only for those who want to relax and kick back on one of its beaches with white-pink sands but also for those who cannot stand cold water or want to enjoy the sea in the winter time.
Yes, that's Santorini. The most dangerous shoe fail happened to me in Oia. The cobblestones are so worn they got shiny and slippery over the decades so that I slipped in my flip flops and left me with bruises. You need to wear sandals or shoes with straps or any laces to support your feet.