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Sailing doesn't have to be social. Some people get out on the water for the sole purpose of being alone. It can be a very contemplative experience to sail along with only the sound of the wind and waves. If you want to relax, sailing by yourself can be pretty good.
San Francisco Bay has a very active shorthanded & singlehanded sailing community. The Singlehanded Sailing Society sponsors a series of races throughout the year, including the infamous Three Bridge Fiasco.
Personally, I like to sail with others but oddly enough some of my favorite people to sail with usually sail singlehanded. It takes a pretty good sailor to be able to handle San Francisco Bay by themselves. You obviously have to know to sail a boat well but you also need patience and a methodical personality to achieve mutliple tasks in the right order. What most sailors break into tasks for multiple people to do simultaneously (turn the tiller, release the jib, adjust the traveller, sheet in the jib), has to be done by one person in steps. It is pretty impressive.
If the singlehanders who race in the Bay are impressive, what about those that sail to Hawaii? Every two years, the Singlehanded Sailing Society sponsors the Singlehanded Transpac, a 2120 mile race from San Francisco to Kauai. That's a lot of miles to be by yourself. I think it takes not only a good sailor to do it but a good person, someone who knows themselves well enough to comfortably spend that much time with only their thoughts (and the daily radio check-in) for company.
It's an odd paradox, that people like this who are so great to be around (as I mentioned, some of my best friends are singlehanders) like to sail by themselves. I think the next event sponsored by the Singlehanded Sailing Society should be a "Take a Singlehander to Work" Day. Invite them out on your boat or, better yet, try to get a ride on their boat. Sign up on a crew list that you want to save a singlehander from their contemplative silence and do some of the work for them. Tell them that you will trim the jib or douse the spinnaker so they don't have to do it all by themselves. Just promise to listen to the sound of the wind and the waves every once in a while.