Ah, this subject takes me back to the years when I lived on a boat. Of course, I was in the navy and boat was a submarine, so my experience my not be applicable. The downside was that it was crowded, 83 men in a sardine can. It was also a bit short on creature comforts. Still, it was a home that went places, and provided food, a place to sleep and interesting things to do.

I also have a friend who lived for 8 years in a sailboat in the Los Angeles harbor. He liked it a lot, and could take the house out for a cruise when he wasn't working. He still has the boat down in the local harbor and he and his wife tour the islands a couple of times a year, so your idea sounds doable.