Yves Engler gives a brief rundown on the history.

Though I don't quite subscribe to his view that merger today would be a continuation of the racist colonial past, since presumbaly these days we would give the people of the potential provinces/territories the last word about whether to join.

I do think that letting Caribbean nations join Canada as full provinces would engender a lot of bitterness in the Yukon, NWT, and Nunavut, which would likely spread to indigineous groups generally.
 
The Virgin islands come to mind. The US purchased "Their" virgin islands in in 1917, so either Canada buys them, or the UK gives theirs to Canada, or both!
 
POD would probably start with a shrinking British Foreign Office after WW1. Remember that Britain was financially exhausted after that ruinous war.
Intitially the FO only asks Canada to assist by establishing a consolate, then pass port office, then RCMP and Canadian Coast Guard are sent to reduce rum-running (under pressure from Washington during Prohibition). As time goes Britain delegates more and more colonial duties to Canada: health, education, financial regulation, navy, army, Air Force, air traffic control, port authorities, etc.
Canadians are tasked with training local (Carribbean) apprentices with the long-term goal of (well-educated) locals eventually administering the island colonies.
Canadian corporations establish branch offices and branch plants on the various islands.
Carribbean colonies are slowly integrated into the Canadian economy and gov't administration.

Frequent migration (over grumpy Americans) would encourage Canadian airlines, AVRO Jetliner, etc.
 

Guardian54

Banned
If you can get a revival of Canadian National Pride circa 1900 in response to the failure of Reconstruction and the spread of Jim Crow laws in the United States, you can see the Bahamas' request in 1911 being approved. After all, Canada was the main terminus of the Underground Railroad, and thus admitting a majority-black province would be an item of national pride and spiting the snooty Americans.

After that you can buy the present US Virgin Islands off Denmark in 1913 if you play your cards right, followed by acquiring the rest of the Virgin Islands later. And then the rest of the West Indies Federation come in line soon enough.

Bermuda eventually becomes part of Nova Scotia too.

For slightly more ASB and rather earlier divergence, I recommend my TL, SI Archives (though there are significant divergences prior to and not covered in detail in the 1912-1915 volume, "Pax Mexicana"). Canada can actually turn Mexico into a de facto puppet if it plays its cards right! And if we get an even earlier POD, well, Russia might decide that since it'd lose Alaska to Britain in any war anyhow, might as well sell it to Britain, who's occupied just holding its empire together, instead of the still expansionist US.
 
I always thought Russia sold us Alaska to keep the British form getting it.
The Russians believed that in a future war Britain would take it off them so they decided to sell it ASAP. They offered it to both the USA, and Britain in the hope of starting a biding war, but Britain wasn't intreasted.
 
POD would probably start with a shrinking British Foreign Office after WW1. Remember that Britain was financially exhausted after that ruinous war.
Intitially the FO only asks Canada to assist by establishing a consolate, then pass port office, then RCMP and Canadian Coast Guard are sent to reduce rum-running (under pressure from Washington during Prohibition). As time goes Britain delegates more and more colonial duties to Canada: health, education, financial regulation, navy, army, Air Force, air traffic control, port authorities, etc.
Canadians are tasked with training local (Carribbean) apprentices with the long-term goal of (well-educated) locals eventually administering the island colonies.
Canadian corporations establish branch offices and branch plants on the various islands.
Carribbean colonies are slowly integrated into the Canadian economy and gov't administration.

Frequent migration (over grumpy Americans) would encourage Canadian airlines, AVRO Jetliner, etc.
In WW2 Canada could decide that conscipts who can't be sent to Europe without volunteering can be sent to the Caribbean to defend North America. Resulting in more Canadian, Caribbean interaction.
 
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