Just to clarify, you want to go sailing while you are visiting some of the Greek islands? OR you want to sail around to the different islands?
I agree with writerbynite, Mykonos is great…I was on 6 Cyclades islands in May of 2008 and I would recommend going in late May if that is your month of choice. It was just a little before their “tourist” season and the weather was chilly, too. Even a couple of weeks later would have been better…
So what to see…all the islands were amazing in their own right. It really depends on your style…one thing is for sure, at that time of year, every island is sleepy. If you are looking for a party, Mykonos is your best bet. If you are looking for complete privacy, Milos was perfect. Santorini and Mykonos are cruise ship destinations so keep that in mind. The Cyclades are very close to each other so if you are looking to sail around, it is fairly easy and you could see many islands in a short period of time.
I am no expert, but I would be glad to give you tips about the islands I saw (Mykonos, Santorini, Milos, Sifnos, Naxos and Paros)…
Hi Thank you for your suggestions! I am aiming for the last two weeks to sail with a Flotilla group along the “Milk Routes?” I want to be sailing the boat around to smaller scenic islands which can be explored in a day’s time. It sounds like the Cyclades best fit that. Did you charter? If so, what company did you use? Thanks again.