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Yes you can by arranging this with your agent or with the cruise line, there is normally no problem here. The problem you may encounter is getting to Cuba as there may not be any direct flights to Cuba from the USA. transit is normally made though Cancun, or The Bahamas or the Cayman Islands. and you can encounter delays in and out of Cuba so you must ensure that you allow sufficient time to make you homeward flight. Now, I may not have my facts right so hopefully someone else will confirm or contra this but at any rate you have some work to do to finalise this....regards...Nei.