We're starting to look into chartering in Greece this summer. The plan is to go the first week of July and we're considering either the Ionian islands or the Dodecanese. We're not currently thinking of the Cyclades because the conditions can be pretty rough at times. Ideally we'd like an area where we can do some good sailing, but also drop the hook in a secluded bay for the kids to go swimming.
I'm looking for advice on itineraries that would work for a one-week cruise. Any pros and cons of either island group? Last year we spent a week in the Hisaronic Gulf along the Turkish coast (vicinity of Simi) - really nice - so I would assume sailing conditions there are not too different from the Dodecanese. Any info on local charter companies would be very helpful too. Any hints, advice, tidbits of information would be much appreciated!
On the Dodecanese Islands you will not get much less windy conditions in July than on the Cyclades. I will be there sailing this year for 3 or 4 months, I mean a bit all around Greece and Turkey and I had been there last year (Ionian, and Aegean).
If what you want, like your post subject, a tranquil kind of holidays with kids and not too much wind, Ionian its the place. You will have medium to strong wind also but normally only in the afternoon, dying at night (while on the Cyclades and Dodecanese in can blow strongly for days and nights). Not a problem if you are sailing there for a month or so: You just stay on a shelter and wait it to blow way, but in a week, if it is blowing hard at that time it can spoil a substantial part of your charter time.
Regarding beautiful places to stay on anchor, there are so many that it would be hard to make a route for a week only. Consider to Charter from Lefkas, go down the channel and them you would have an incredibly beautiful scenery with several green mountainous islands around at short distance. You will not have time to explore them all and if you can make it for 2 weeks I strongly advise you to do so. The Islands:
Lefkas, Meganizi, kalamos, Kastos, Skorpios, Itaka, Kefallonia, Zakinthos.
That's not by accident that Onassis chose one of those Islands for having his summer house, in fact he owned the entire Island
Instead of telling you about favorite sites (I have sailed there on two seasons anchoring every day and I am far from knowing all anchorages) I strongly suggest you to buy this Pilot book, it is inexpensive and very valuable: