Thanks for the feedback - very helpful. And Prompts a few more questions: for JP - who did you charter with? Bareboat? Captain? For both JP and TS - would Sept. be more agreeable wind-wise than Oct.? Any issues with jellyfish (heard this is more a problem in the fall). Some of us are leaning toward the fall because the water and air temp. should be warmer, more conducive to swimming but there are other factors to be considered as well (jellyfish, wind, other). Thanks.
I was not chartering so I can't offer any insight there.
I was sailing in the Aegean during the summer months of June, July, and August. I don't recall seeing any jellyfish while swimming, but we occasionally saw a random one out in deep water while passagemaking.
As summer progressed, the strength of the sun diminished, making it more comfortable (in early/mid-summer, we had temps as high as 49 deg. Celsius). However, while the sun diminished a bit, the Meltemi increased as the summer wore on -- especially in the islands.
Between islands the Meltemi usually accelerates and makes for challenging but fun sailing, Force 6-7-ish. We would often duck under the leeward side of an island for a break, rather than passing it on the windward side with a lee shore below us. The nice part about the Meltemi is that while it blows strong it is a mostly cloudless wind, so it doesn't seem dark and stormy/intimidating.
September would probably be a nice time to charter. Like the U.S., many europeans vacation during August, so you might have fewer tourists.