As a former professional delivery skipper
in the US (100 ton master with sail and tow endorsement), We chartered an Alba 55 in Greece
for 4 weeks quite a number of years ago. We opted to hire a skipper
affiliated with the charter company but not the vessel owner because we wanted a relaxing vacation
with someone who spoke the language and was familiar with the not so travelled spots among the islands. We went in mid-May, picked the boat up in Rhodes and sailed both the Sporades and the Cyclades
island groups. At the time of year you are planning your trip, I would spend it in the Cyclades
as the water
is a bit warmer as I recall
. The Melteme winds that come out of the north can make crossing between the Island chains problematic in May-June I believe but the charter company can advise you on that.
Other than the PNW, the Greek Islands
are some of the most beautiful you will find anywhere with the added advantage of the historical interest on many of them.
My father joined us for a short part of the trip and while he could take or leave the sailing, his interest in the history
of the islands and the food
made it a memorable trip for him. He was in his 70's when we went which made hiking to some of the more interesting spots a little difficult but he said he wouldn't have missed it for the world. Hope this helps with your planning... cheers, Phil