First, know that importing cigars from Cuba is considered illegal. The United States placed economic sanctions on the Cuban government in 1963. Ever since then, Cuban cigars have become the holy grail of cigar enthusiasts. There is, however, one loophole: visitors to Cuba who return from a sanctioned and licensed visit are allowed to bring back cigars. However, visitors are not able to bring back more than $100 worth of cigars, and they must be intended for personal use, and not for resale.
Any other ways of obtaining Cuban cigars is considered illegal. It is in fact illegal to buy, sell or trade Cuban cigars in the United States. Fines for illegal trading, buying or selling of Cuban cigars may face up to $55,000 in civil fines. This type of fine, however, is quite rare. The more likely scenario is that you’ll have your cigars confiscated.
When purchasing a box of Cuban cigars, be prepared to fork over quite a bit of your cash. Prices can range from about $150 to $500 or more. If you’re offered a box below these prices, chances are it may not be the real thing. Most Internet businesses that sell purportedly genuine Cuban cigars tend to be imitations. Always avoid shops or retailers that offer “discounted” Cuban cigars.
How to get your hands on the real thing? The easiest way to get a box of authentic Cuban cigars is to head north to Canada. Buy them in Canada and repackage them so that they are not in their original Cuba packaging. Remove the rings and place the cigars in a different box. Customs agents tend to not inspect cigars carefully, and it is generally not considered a serious offense to bring Cuban cigars into the United States. In fact, many clerks at tobacco shops will even offer to repackage Cuban cigars for you.