Carry a VHF radio operator's license, because you won't always know what a country requires, and remember your boat's flag state sets your licensing rules, not the country you're visiting. Keep your ducks in a row so a boarding never turns into a problem.
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The French islands are the easy ones, with Martinique, Guadeloupe, and the French side of Saint Martin offering relaxed check-in where nobody's counting your days. If your paperwork blows overboard, call ahead and be upfront, because being honest gets you further than hoping they don't ask.
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It looks insane, but a good launch is slow and deliberate, and when your boat is in someone else's hands, your only job is to stay out of the way and let them work.
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