Husband and I are just starting to plan a two week trip to Greece at the end of September 2015. Most likely will need to book the trip for arriving into Greece September 26. There's a slight chance we could leave the weekend before that, but it will be difficult due to my husband's work schedule. Planning to keep the islands for the first leg of the trip and cover Meteora, Delphi and Athens afterwards.
From what I've read, some islands are more active than others during the time of year we will be visiting. We would ideally like to spend a few nights on two different islands to get a little variety and our activities would include relaxing, swimming, lounging and maybe snorkeling. Good shopping would also be a plus. And, of course, looking for some of that picturesque scenery, would love to see some of the postcard white sand beaches and caves. We are very interested in Santorini and it sounds like it would still be going strong. Milos looks wonderful but it's one that I've read about that sounds like it really slows down during the time we'll be there. Looking for anyone's experience with different islands for the time of year we will be there and the pros/cons of your experience. Thanks!