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I suppose for many sailors the idea of sailing off to visit all sorts of exotic places taking their home with them has enormous appeal. I for one really dislike flying... packing a small bag... finding a hotel... and doing tourism. It works for big cities like Barcelona, Paris, London. But there are all those beautiful places off the beaten track on the water...and lots in the tropics. Sounds like a plan. If you can do a downwind plan even better.
Sailors starting on USA East coast are going to be sailing hard on the wind to get to the eastern Caribbean most of the time. This is no fun if your always sailing heeled way over. At least the weather is pleasant. I would imagine that many decide this sort of sailing is not so pleasant... and decide that they've been there done that and it's time for something else. Perhaps they decide to become weekend local sailors going out with a fair forecast... but no exotic locations. The coast is full of lovely destinations... Or maybe the care of a boat is too much for the "fun" owning a boat can provide and they chose to exit and do something else for their leisure activity like RVing, skiing, etc.
I suspect it may become a cost / benefit analysis. Cost means both work and money. We love staying aboard in a lovely harbor whether we sail or not. But the boat still needs to be maintained. We don't have the urge to day sail... been there done that. We still love fair weather sailing. I will give it one more season and see how that goes.... but I will start preparing a Sale by Owner listing, Almost had a partnership which was a way to have our cake and eat it too. That fell through. Hope springs eternal.
 
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