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The easiest way to enjoy a real Cuban cigar is to buy one from a reputable Cuban cigar dealer or a good hotel while in a country that sells Cuban cigars legally. It's worth it to pay top dollar for a really great Cuban cigar, enjoy it, and then make it part of your vacation memory.
Despite popular belief, it is not acceptable to bring Cuban cigars into the US if purchased from Canada, England, or Mexico.
Never, ever, buy a Cuban cigar from a hotel. The ONLY place to buy a Cuban cigar while abroad is in an authorized LCdH store. Otherwise, keep your wallet in your pocket, because you're going to get ripped off. Just because it's legal for a country to sell Cubans doesn't mean the Cubans you'll be buying are authentic. In fact, it's that exact myth that results in countless uneducated enthusiasts getting ripped off every day. This is quite possibly the worst tip on this page.