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