Join a sailing club, get a community. I joined Jib Set to update my sailing experience and have not regretted it for a second. Plenty of opportunities to get out on the water as well as meet people of similar mind. The membership costs are roughly $ 170 a month(year round) — enough to weed out the riff raff but affordable for those serious about sailing. And there are minimum annual volunteer hours which further contributes to the communal environment. Sail On!