Cuban Relations, Idiosyncrasies, Formalities
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First off, Cuba names a lot of Officials. There are at least a dozen individuals that cross your path, look at your passport, ask similar questions, and get their palms greased before you're cleared into the country.
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In no particular order we met, and tipped, the following:

Guarda Health Inspector (for a temp reading)
Guarda Vessel Inspector
Guarda Passport Stamper
Dept of Agriculture Vegetable Counter
Dept of Agriculture Vegetable Counter's Asst
Marina Man that Catches a Line
Marina Man that hooks up shower power
Marina Man that tells you the Dockmaster is coming
Dockmaster
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In all, it was a easy and painless process. We had our ducks in a row, Talia's paperwork ready, our smiles shiny, and a few small USD bills.