Where to start
Buying Cuban cigars online seems easy at first blush. A simple Google search will yield tons of websites offering Cuban cigars online. If you are not an American and do not live in America the process is easy.
Just find what you are looking for, pay and wait by the mailbox or whatever non-Americans do to get their mail. On the other hand if you are an American trying to find Cuban cigars online your challenge is much greater.
First and most importantly, buying Cuban cigars online is illegal. Buying Cuban cigars online is just as illegal as buying them on the black market or smuggling them into the country. The law in America is that it is illegal for an American citizen to buy, sell, or possess Cuban goods. UPDATE 2017: Americans traveling outside of the US are now allowed to bring Cuban cigars back into the US. It is still illegal for cigar shops in the US to import and sell Cuban cigars.
Buying Cuban cigars online does not get around this law. Because this is the case, although you may find someone who offers Cuban cigars online and says they will deliver them to you in the United States, you will be hard pressed to find a site that will guarantee delivery.
This is because the US postal service and customs officials can commandeer any Cuban goods they find. So if you buy Cuban cigars online you can never be sure they will actually get to you.
But if you are comfortable with the legal implications of trying to get Cuban cigars online, there are some other concerns you should be aware of. As with any online purchase there is a certain level of uncertainty that goes along with the purchase.
Everyone has had an experience with buying something online and getting less than they expected. Whether the product was described incorrectly on the website, or the size or dimensions just didn’t turn out as predicted, this happens a lot. With Cuban cigars online, you run into the same potential pitfalls.
Cuban vs. Dominican
There is no way to be certain you are getting what you ordered. Unique to the fine cigar market is that unless you have a very well trained palate, you probably cannot tell the difference between a Cuban Cohiba and a Dominican Cohiba.
That is to say, an online seller can package up anything and call it a Cuban cigar and you will not really have any independent way of discerning whether they have delivered on their promise. So buying Cuban cigars online is a dicey business.