I am finishing a 4 months cruising plan for Greece and I have made a lot of research. Not sure I can be of help since I am looking to stay out of marinas and not in, but then I will be sailing the boat all time.
With adequate planning I don't think you will have a problem. It will imply a careful planing regarding the points you are leaving the boat and careful planing to be at those spots in time to leave it. Then you will have to catch a boat to Athens to catch an airplane back home.
The problem with Greece is that the information is nor readily available and with all those Islands it is difficult to integrate all the information from a pilot Book in a coherent voyage plan. From my own experience, doing that will take a lot of time.
Firstly, I'm not sure if I'm replying in the correct 'box'. I'm a new user (if that's a good enough excuse).
Well PCP, many thanks for your helpful response. I am slowing coming to the conclusion, that the first cruises I make can only be planned in shortish hops. Thanks again.