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The original was posted on /r/sailing by /u/RecoverOk9666 on 2025-07-09 18:51:25+00:00.

I learned to sail about five years ago and started chartering in Greece—just 1 week per year at first. Over time, that’s grown, and this year I’m up to 3 weeks. I’m now considering doing 6 weeks next year, as more friends (and friends of friends) are getting interested in joining and many have become regulars.

I’m thinking of splitting the time between May/June and September/October to avoid the peak season heat. Cost and income aren’t a limiting factor, and my experience so far has been great—which is why I want to do more of it.

Are there others here doing something similar? I’d love to hear your experience. Can it ever feel like too much? Any unexpected challenges?