[quote=@ClocktowerEchos]
<Snipped quote by Dinh AaronMk>

Again, something I can accept but I'd think it'd only really be an issue for the southern most nations as I don't think small ships can get from the islands to the north without stopping.

Although that does bring up the interesting idea of them having pit stops along the way north in territory where they're grant special permissions and contracts by the local rulers to dock there for a certain fee or mercenary work. It could also be a clan-by-clan sort of deal where collectively they're known as the "Rum Roaders" <working title> or something but they're actually a whole bunch of different factions with some being more trade focused and others more raid focused.
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I'd think Cuban cities would be the earliest places for them to stop where sugar cane may be grown to enough of an effect they can continue on to the mainland US. Travelling around the Florida keys and into Southern Florida itself might be the next earliest stop. And then like the Silk Road they sell everything there or most of it, get their staple foods and stuff to trade back on the route home and then go back to Jamaica or beyond. It'd be such a bucket-line as the Silk Road was that no one might ever see a Jamaican, but they'll certainly handle their rum as it travels beyond along the Mississippi or other river routes.