I did a nude sailing holiday with Gaysail in a round trip from Mykonos to other islands in the Cyclades about four years ago. It was well organised and the islands were all interesting and slightly different. The boat was a little cosy for the number of people so you need to be fairly easy going and tolerant of others. Most of the guys were there as couples or friends travelling together so it's not always so easy for guys travelling alone. I went mid September and the weather was okay but unfortunately there was too much wind and the sea was very choppy. I have been back to Mykonos every year since and like everywhere the weather is variable. With respect to the sailing I would recommend the experience but best if you're an outgoing kind of person. The guys at Gaysail were quite happy to discuss the holiday before I booked up so certainly worth making contact with them as asking for specific details.
Regards

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Just to add to the details; there was no sexual agenda on the Gaysail holiday. It was just guys enjoying being naked in the sunshine and skinny dipping. The age range will vary for each holiday so difficult to be certain but the guys I was with ranged from 20s to 60s and a variety of nationalities.

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not actually a sailing trip but on a motor (speed) boat on the lake when we ankered down in a bay with other boats we saw other guys/girls were hanging nude on their boats so me and my friend did the same. Enjoyed the whole afternoon in that bay and went nude swimming as well. It seems to be that it is quiet common to be naked on the boats.

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