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Cuba
Cuba
I flew myself and my bike from Caracas Venezuela to Havanna Cuba in 2004. It was not an easy task, getting the bike into the cargo plane was the most difficult. As I was the second motorcycle traveler to collect his bike at the cargo terminal at Havanna airport (a Japanese rider had been the first, according to the head of customs) it was not that difficult to get it out and on the road. They have a standard process with forms to fill out, and I had to get a Cuban numberplate.
So, you can fly your bike to Havanna, if you find an airline willing to take it.
But I would say, that renting anything with engine is the better option, if you can find somebody willing to rent. In 2004 I met one traveler in a rental car.
I did not like Cuba at all, so I only stayed for ten days before boarding a sail boat.
Enjoy your journey.
mika 
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