Shipbucket

All right, very rough idea, but how about this:
Toussaint Louverture is never captured by Napoleon's forces, and remains in power post-Haitian revolution.
Dessalines never comes to power, and Toussaint doesn't order the mass-executions and the 1804 massacre never happens.
Instead, the new regime follows the spiritual footsteps of the French Revolution, and while dragging down the French colonist's absolute hold on power, they are either integrated, or expelled.
As such, Haiti isn't nearly as ostracized as it was originally, and actually gains some influence and power.
Using this as a template and inspired by the success, the 1812 Aponte Slave Rebellion in Cuba gains much more support from the free black population, and pulls off a similar victory.
We now have a free, black run Cuba and Haiti. French-Haitian relations are healed, and Cuban-French relations soon follow.
Spain tried to re-take Cuba, France intervenes, and the Dominican Republic is the next to fall to freed slaves, and the Unification of Hispaniola is a success.

Part of the cause for the US Civil War is (in addition to everything else), the South pressing to end relations with Cuba and Hispaniola.
During the US Civil War, part of the South's attention is focused on Cuba and Hispaniola; which sees the two come together for mutual protection, and gives birth to the Cuban-Hispaniolan Navy.

Following the end of the Civil War the two work to promote Emancipation Movements around the Caribbean, netting the islands you mentioned.
Around this time, the Communist Manifesto makes the rounds in the region, and the world's first quasi-Communist nation is born; more a confederation but still..

Friendly relations with the US and France (Britain is not so keen to have lost territory in the region), sees economic success.
Eventually, they get really cuddly with the Soviet Union in the 30's, and joint the allies with WWII.
However, with the end of the war, they go down the path of choosing the Soviets over the Free World; and so are very early adopters of Soviet technology, and recipients of Soviet aid.
That gives you plenty of lee-way and funding to build/do as you like.

Anyway, that's just off the top of my head.
Thoughts?

That's just off the top of your head!?!? That's incredible. I'll start work as soon as I have time, I have a bunch of school work to do.

Bah.
The reason I'm a lurker around here, is that I'm totally over-awed by the artistic and maritime engineering expertise and talent here. I'd love to be able to pull together ships like you guys do, but...

Well, I tend to be better at the history side of things rather than the ship building thing. So, if I can help out with the historical context/political-economic side of things, I'm more than happy to contribute. I'm more than a bit flummoxed when it comes to the ships.
Still; LOVE the artwork here.

Anyway; let me know if I can help, and I'd be more than happy to help fill out a back-story, etc.

Sure thing.
I'm a bit busy over the weekend, but first thing on Monday; no problem.

Coming a bit late to the game here, but I felt like adding my $0.02 since this AU concept hits closer to my ballpark than most.
Shurik's idea here of turning Louverture into a sort of Carribean Bolivar is enticing, but I'd like to find a POD closer to home, i.e. to the middle of the 20th century. My reasoning being that the further back you start, the harder it gets to shuffle things back into something half recognizable as a "Cold War" setting with all the butterflies set loose along the course of one century. Still, this is made more difficult by the comparative political stability of most of Latin America during the early 20th century. As opposed to Africa or South Asia, no short path to Marxist revolution through imperial loss of control during the World Wars and subsequent decolonization for them.
So just for the hell of it, here are a couple of pathways that might make some kind of sense. Please take them only as pointers and eminently open to discussion:
- Political influence from Spain following a Republican victory in 1936 or a massive wave of Republican Communist/Anarchist exiles, leading to local leftist movements coming to power before 1940 and then being buttressed by the Allies as a bulwark against German-leaning reactionary forces?
- A more interventionist US government in the Wilson era (or any earlier time after the Civil War) goes for full hemispherical hegemony through right-wing corporatist banana republics, exciting revolutionary sentiment on a wider scale, while the Depression and the end of the Russian Civil War in the late 1920s conspire to reduce the US projection capabilities in South America, leaving an open field for Soviet-backed (or hell, Trotskyite-exiles-backed) popular revolutions?
- A completely unrelated neo-Bolivarist Latin American Union movement takes hold is a handful of major countries and turns to the Soviet Union for diplomatic support when political pressure from the US becomes unbearable?
- All of the above? None of the above?

Anyway, I'll stick around as much as I can to see how you make this turn out; it's always interesting to dabble into alternative historical lines like that.