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So the next few weeks looks good weather wise for Crete and Santorini.

When forecasts report 60's in the evening...based on humidity would that be a chilly 60? It looks like a light woman's jacket would be appropriate, but for those of us who run a little on the cool side, would this be warm enough? Also...on ferry boats? Cool? cold? I'm trying to figure out what jacket to bring. Winds?

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May can be windy, so it can feel cold after sunset. The best idea is to bring clothing you can comfortably layer, to compensate as needed.