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Not that Cuban cigars are as good as they use to be but . . . . . . . .
Have seen them in the BVI.
From what I know (which isn't much) the U.S still has a trade embargo with Cuba and that would include the Cigars. I believe that the same applies for the USVI (and other territories of the United States. Not sure about the Black Markets though.
Oh yea - DAA - forgot about that. A friend just came back from Barbados and had some - guess that's not controlled by the U.S.
Actually it is considered as contraband. More so if you bring in a large quantity. But the guys at customs probably won't mind if you bring home a few for personal use. I guess it would depend on which custom agent you end up going through. Do you feel lucky?
You can get cubans in British Virgin Islands. Customs will not let you bring them back into the US. They will give you a hefty fine and everytime you get on a plane to go anywhere you will be in there database and they will search you and your stuff.