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I agree that it is not necessary to drop everything when taking up a "cruising lifestyle". I've been fortunate enough to be able to finagle a way to work for 1-2 months, then sail for 2-3 and then repeat ad nauseam. Not only will that pay the bills but it gives me enough time to plan long passages with respites inbetween and have large portions of a circumnavigation paid for. The best of both worlds.
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