Cuban cigars are some of the most coveted prizes of cigar connoisseurs. Part of this is due to the sheer quality of many Cuban cigars. Cubans were a favorite of Winston Churchill's, and he made sure to keep himself with a steady supply of them throughout his life — a fact which certainly contributed to their high estimation, since Churchill was and remains iconic, and the cigar was his ever-present trademark. But the other (and perhaps more significant) cause of the desirability of Cuban cigars is the difficulty involved in obtaining them.

Cuba came under communist control in 1959, with the ascendancy of Fidel Castro's regime. Soon after came the Cuban Missile Crisis, and President Kennedy put in place the Cuban Trade Embargo, which is still in effect today. This didn't ban all premium cigars, but the most popular cigars (Cubans) were banned. In 2004, the embargo was made even more restrictive, and today it is not only illegal to bring Cuban cigars into the United States but it is even illegal for an American citizen to buy or smoke Cuban cigars while traveling abroad.

Will Cuban cigars become legal in the United States any time soon? Some argue that the trade embargo on Cuba should be lifted, since it seems to hurt Cuba's people a good deal more than it hurts Castro. There is also the fact that the U.S. does not have similar embargoes in place with countries. But given the history of relations between the U.S. and Cuba — for example, the reported 638 assassination attempts on Castro by the CIA — getting Cuban cigars legally in the near future doesn't seem terribly likely.

There are those, of course, who obtain Cuban cigars by illegal means. The risks are high, since fines for breaking the embargo can run into the tens of thousands, especially for those who try to smuggle large quantities of Cuban tobacco into the United States. American tourists traveling abroad sometimes ignore the 2004 restriction on Cuban cigar consumption, and admittedly the restriction would be difficult to enforce effectively, but in doing so they run the risk of unscrupulous vendors selling counterfeit Cuban cigars.

A cigar smoker who truly appreciates high quality and is willing to pay a high price, but who isn't willing to break the law, will find that cigars from the Dominican Republic (such as the Fuente Fuente Opus X) or from Nicaragua (such as the Padron 1926) are of comparable quality. If you're not a cigar connoisseur, though — if, honestly speaking, you can't tell a five-dollar cigar from a fifty-dollar one — there's no reason to go searching after Cuban cigars. Just smoke what you enjoy.