4. Be self sufficient. The most frustrated/unhappy cruisers we have met are those that aren't able to maintain their boats and/or who's boats are in poor cruising condition. When things break, they are at a loss. Nearly every time they make a passage, something fails - adding to the overwhelming list of things to fix. If you are not prepared to fix these things, be ready to deal with a local who will not only charge you an arm and a leg, but might not even be able to solve your problem (oh, and you won't figure this out for two weeks). Not everything can be fixed by you and eventually you will need to employ the skill of an expert, but being able to fix the small stuff on your own will help you tremendously.