Not certain how much sailing you want and how much time in any one place - but you've lot's of nice islands to choose from plus the oft forgotton mainland.
IMHO Milos and Ios are nicest - and Ios nice and safe to leave your yacht and go visit Santorini by day ferry
But use google earth
and go look at each one. The way Google Earth
is now getting populated with pictures, it is the best way to check out possible locations.
We did cover some of the cyclades
this past summer - so if you want comments on those and some added pictures of anchorages
etc go back in our blog to early June - Swagmans Sailing Blog