AH challenge: Commonwealth of the Caribbean

Your challenge if you accept it is to somehow gain as many Caribbean possessions for the British empire as possible
 
Your challenge if you accept it is to somehow gain as many Caribbean possessions for the British empire as possible

Well, you could get the rest of the French and Dutch ones by having Napoleon winning or defeated with more British losses, or defeated primarily by the continental powers.

Potentially have the Peninsular War end slightly afterwards by a seperate peace treaty in which Britain gets Santo Domingo and Puerto Rico, then buys the Virgin Islands from Denmark.

Cuba is really difficult though. A protectorate over it is possible.

And I'm not sure how long this would last for.
 
Treaty of Paris: swap Minorca with Cuba? And then have it survive the American revolution intact
 
With a napoleonic POD i can see: In exchange for British support for their revolution Haitian leaders agree to become a protectorate, then during the congress of Vienna they are given the French Windward Isles. A few decades later in a deal with Denmark they buy the virgin isles, from there they control everything but the Spanish possessions and its much harder to get those since they're the almost the entire Spanish empire by that point and this they're much more hostile to losing them whereas the French Caribbean was other than Haiti rather unimportant.
 
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