Re: First charter: advice needed for Europe
We chartered in the Dodecanese Islands in Greece - offseason (October) - was cheaper that time of year. It was very quiet on several of the islands we visited - such that there were only the year-round locals that spoke no english. That wasnt a problem as everyone was very friendly. We did not have any EU sailing experience so were a little nervous about big crowds during summer. We sailed out of Kos and worked our way down to Rhodes. We weren't very experienced at the time, so our med mooring routine at the end of each day with just my wife and I on a 36' was highly entertaining for onlookers.
We chartered with the Moorings since we had used them several times in the BVI and since we didnt have a lot of experience, were more comfortable with a larger outfit / a safer bet in case there was an issue with the boat while we were out and about. All in all, it was a great experience. Good luck!