It feels like this is an entirely impossible undertaking, with so many obstacles and so much misery waiting for you if you try.
Starting with a ticket price of 420 Ls, moving on to the dreadful weather, and ending with the awful roads inside the island. It's also worth mentioning how exceptionally easy it is to wreck your bike on those very roads, and the complete lack of bike shops—or any other shops for that matter—in the island's interior.
But people do ride there, they really do.