It's possible to swim in the sea at this time of year but it's generally a little too cool for most. The average sea temperature is 20 C.
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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).
Temperatures throughout Greece can vary, but May is a good choice for heat and sun in moderation. Temperatures: Average highs of 24 degrees celsius, average lows of 10C. Rainfall: Ranges between 13mm per month in Crete to 31mm in Corfu. Sunshine hours: Nine hours per day.
Crete. Crete is the southernmost island in Greece and enjoys average May daytime temperatures of 23 degrees/74 Fahrenheit making it one of the warmest greek islands to visit in May. The water is usually warm enough for swimming and the weather is usually calm, with occasional showers.
Visit Santorini in Spring & Fall (Shoulder Season)The Spring & Fall (shoulder season) is from mid-April to June and from September to mid-October. With most establishments still being open and fully functioning but without the high-season crowds, spring and fall are hands down the best time to visit Santorini.
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).