Living on a sailboat was something we did for eight wonderful years … all in the Caribbean … Trinidad to the Virgin Islands. When you sell the boat, it is called "swallowing the anchor". We did so in 2002 … we are constantly asked if we miss it. Sure, we do … but
Things we do not miss are the maintenance and up keep the boat requires … for example, the exterior teak needs to be sanded and varnish applied. This must be done once a year. Now it is no problem if you are in Venezuela, you can get day labor for $ 10 a day to do the sanding for you. If you have to do it yourself, it will take 3 days or so for the two of to do the sanding. You must do it at first light to about 10 AM … the deck is too hot after that.
Other fun boat maintenance I do not miss is keeping the waterline free of algae. You do this from your dinghy or with your snorkel gear. It is a pain, but it has to be done. Going up the mast to replace a running light bulb was never the highlight of my day. It was about 53 feet off the deck. The bosun chair will never win any awards for ergonomics … trust me on that.
The usual stock answer we give is to do you miss the boat is; "we would not take anything for the experience, it remains the highlight of our 35 year marriage, but we are glad we did it when we did."
When we swallowed the anchor I was 57, now I am 64. Do you know anyone who is in better shape at 64 than 57? I thought so … if you have a yen to be living on a sailboat, I would do it as quick as you can.
The saddest thing about folks that would like to try living on a sailboat, is saying; "When I can afford to buy boat X or boat Y … then I will do so." Most everyone who says that is still on the dock. Go with what boat you have now, to wait may be too late. Enjoy.