[JohnRPollard]

Many years ago, I spent about ten weeks sailing in the Dodecanes and Cyclades. It was fun, boisterous sailing, with abundant breeze from the Meltemi. I think the Meltemi is not quite as potent in early/mid June as it is later in the summer, so it may not be a big deal for you. But even if it's blowing good, there are plenty of options to duck out of the weather. If you need a break from the wind, you can often choose to pass an island on the leeward side in the shadow.

There are so many destinations to choose from, your best bet is to study some guides and figure out which islands and harbours appeal to you most.

A word of caution about Santorini (Thira). It is a unique and beautiful destination, not to be missed. However, it is not necessarily the best island or anchorage to visit by small sailboat. When I was there, there were only a few huge mooring balls, in a rather exposed section of the harbour. Anchoring is tricky due to the depths (you're basically dropping hook inside the cone of a volcano), and the harbour area has a lot of ferry traffic and wakes.

My info on Santorini may be dated, so check the latest cruising guides. In the end, we chose to leave the boat safely anchored at Ios (I think), and made a very memorable day trip by ferry boat to Santorini.