How to Purchase Cuban Cigars

So you want to want to savor the flavor of communism, eh? You may not know a Romeo y Julieta from a Swisher Sweet, but the allure of smoking smuggled goods is too tempting to pass up. Buying Cubans isn't the hard part--it's not getting duped that's difficult.

Instructions

Difficulty: Moderate

1. Know what you're getting into. Ever since the United States placed economic sanctions on the Cuban government in 1963, it has been illegal to import Cuban cigars into the United States. But there is an exception: Visitors returning from a licensed visit to Cuba can bring Cuban cigars into the United States, provided the cigars are for personal use (not resale) and that their value does not exceed $100.
2. Be aware of the risks. It's illegal to buy, sell, trade or otherwise engage in transactions involving Cuban cigars in the United States, even if they were purchased from a foreign country via the Internet. You may face civil fines of up to $55,000 per violation and criminal prosecution, but the more likely punishment will be the confiscation of your cigars.
3. Expect to pay $170 to $500 for a box of Cuban cigars; anything less is suspicious. Dozens of online retailers will express-mail boxes of "Cuban" cigars to you anywhere in the world, including the United States. However, most of those mailed to the States are fakes, regardless of guarantees. And since you were trying to make an illegal purchase, you really have no one to file a complaint with.
4. Go north. The easiest and surest way to get Cuban cigars safely past customs is to buy them in Canada and repackage them. Remove the rings and place the cigars in a different (not Cuban) box. Clerks in many Canadian cigar stores will do this for you, but watch for the bait-and-switch. Most customs agents won't bother to detain you over unidentifiable cigars (it's not like you're smuggling heroin). Replace the rings after you return home.
5. Play it safe. If you just want to smoke an authentic Cuban cigar while you're traveling abroad, purchase one at an upscale hotel. You'll pay top dollar, but you'll most likely be buying the real thing.

What to Look For:

• Risk of fine and prosecution
• Fake Cubans
• Internet retailers
• Canadian cigar stores
• Upscale hotel abroad

Tips & Warnings

• Avoid cigar stores that advertise Cuban cigars, particularly "discounted" Cubans--you're being targeted for a reason and are probably being sold a counterfeit.
• The easiest way to spot a fake is to inspect the ring. If it's loose or out of place, the cigar is either fake or dehydrated. Also, avoid Cuban cigars wrapped in plastic--a sure sign that they were made by machine.
• Never smuggle Cuban cigars in from Jamaica. Customs officials routinely suspect Jamaican visitors of smuggling marijuana and inspect their bags thoroughly.