In the SF Bay Area, I lived on a sailboat for about 5 years. Living in a constricted space like that definitely takes some time to get used to, but I enjoyed the experience quite a bit. Sailboats are great if you want to break the habit of keeping a lot of possessions; I had my own rule that I would always be able to get the boat ready to sail within 30 minutes which meant that everything I owned always had to be either tied down or stored in a cabinet somewhere. Keeping a space that small clean was pretty easy.

I was a liveaboard in one of the marinas in So. San Francisco, so I did all my showering, etc. using the public facilities. One perk I gave myself was using cleaners for getting my clothes washed, which regardless of where you live, is pretty awesome.

I hadn't ever sailed prior to buying a boat but I spent 4-6 weeks taking group lessons and reading up on boats, and by the time I was done with my class, I had purchased a boat and was moving in. There is a lot to learn not only on how to sail but deciding what type and model to purchase.

The winters kind of sucked; it can be a little bumpy and really noisy when there is a storm, and walking 500 feet or so to the public bathrooms each morning in the rain isn't all that fun. The rest of the year was great though and I did spend quite a few years sailing around the bay on weekends.

Sailing is definitely a cool sport for hackers who like to know how things work and get optimal results. It's an interesting mix of science and history.

I'd definitely recommend it for a single person in high tech if they are so interested (unless they have a propensity to get seasick).