We chartered in Greece twice. Hubby has his Masters so not an issue but they were particular about credentials.
We used a company called seafarer holidays and joined a flotilla.
It was incredible both times. Sailed a mono in both the Dodecanese and paloponese areas.
Food and culture is spectacular. I have made many posts over on the world forum about our trips.
And yes the med Moore is difficult in some places. One small Harbour ( Symi ) was particularly challenging but we did it!
We loved the area so much we spent 3 weeks land based in Greece last year.
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