Cycladic Islands weather?

It's probably a bit early to get an accurate forecast for the end of May; you're probably just seeing averages. By two or three days before departure, you should have more accurate info for the first few days of your trip, at least as far as temperature goes. I find precipitation forecasts much dicier, though perhaps that's not an issue in Greece at this time of year.

I was last in Greece decades ago, in September, and what I remember is that it got quite cool and breezy near the water as the evening wore on. My very cold-natured mother was uncomfortable despite wearing slacks, a long-sleeved blouse, a light blazer and an unlined trench coat.

Remember that the temperature at 8 AM and at 9 PM may be very different from the daytime high. I don't take shorts to Europe because I'm not interested in going bavk to my hotel to change clothes as the temperature rises and falls, and I don't want to cart around a large bottle of sunscreen.

At most you will need a pair of lightweight slacks and a long sleeved T-shirt or light sweater. Wear them on your flight and you are set. No need for anything heavier. Sea likely too cool for swimming, but pools should be ok once you get moving.

Mid-70s would be plenty warm for me to swim, assuming there are not the high winds that I see predicted for this week in Mykonos, for instance. My preferred swimming beaches tend to be the more sheltered type, as well, with a better chance of the water warming up. Weather.com is currently showing a very narrow range between afternoon high and overnight low temperatures there (68-72) both for this week and for every hour of the current overnight (almost making one wonder whether the weather station is broken).

We are heading to the Cyclades as well the latter part of May-early June. My weather ap shows mid to upper 70's for day and low 60s at night. I am bringing a cotton cardigan and a light hoodie to layer as well as jeans and light pants for evening. I have been checking the sea temperatures and they have been around 70-72 degrees - good enough for us to swim. We are used to summer Lake Michigan temps and anything above 70 is a treat! The only thing that concerns me is wind.

Keep in mind the overnight low will likely be reached around 3-4 AM., not 10 minutes after sunset.

You should not need a lot of 'bundle up for warmth' clothes

My husband wears the zip off long pants with a golf shirt. Tucked in shirt and long pants, he looks ready for a nice dinner. Warmer during the day, he zips off the pants into shorts, untucks his shirt, and he is comfortable on the beach.

It is not that cold at night. You'll need a light jacket or a cardigan or even a hoodie. It is possible that you will be on the beach the whole day, so there is no need to pack many tops and t-shirts. Just one for each day is enough. Two bottoms for every 5 days. In Greece, the best option is to take with you trousers as well as shorts because some days the weather is really hot and some other, especially on the islands, at night the temperature is low. I always pack a pair of light jeans ;) Flip flops are perfect for the beach and walking around the pebbled streets of the Greek islands, but of course, you have to take another pair of shoes. In autumn and winter, snickers are perfect for sightseeing and feeling conveniently when walking around the city. I am going to Mykonos this weekend. Today I am going to plan what I'll pack. All of the above included. I might try to swim, some friends already gone twice to the beach, I still feel a bit cold. However, I'll be on one of the best islands around... so I wont miss it. My brave self will take over, so should yours!!!!