Let me offer a totally legal alternative solution to the dilema of purchasing Cuban cigars in the USA. First, I will tell you I have dual citizenship as an American - married to a Brazilian - living in Brazil, where Cubanos are perfectly legal. I was initially enamored with the possibility of overtly buying any Cubano I wanted. However, I soon found them all to be terribly expensive. Seems the Communists in Cuba don't have much regard for the working proletariat in other countries. But I eventually found a handmade Brazilian brand that is grown from the same source seeds and under the same growing climate as those of Cuba - Alonso Menendez brand of premium cigars, regular and maduro. I do not work for this company nor have any affiliation with them beyond smoking their cigars nearly exclusively now. The name Alonso Menendez refers to the originator and co-developer (along with Ramon and Francisco Garcia) of the Monte Cisto line of cigars in the early half of the 1900's and later, co-owners of the Upmann Tobacco Company in Havana. When Castro came to power in Cuba, rather than nationalize his company, Alonso packed up his family, his proprietary cigar making technology, seeds and sailed off, eventually finding a replicated home climate in an area in the state of Bahia, in Brazil. His son Felix has carried on the Menendez family tradition of making the finest cigars possible from the original Monte Cristo lineage of seeds.
I know I sound like a salesman, but I have found simply from experimentation and trial and error that the Alonso Menendez maduro robusto is every bit as rich, full-bodied and Cubano-like flavored as the Partagas Series P #2, that used to be my "go to" cigar, but at one third the price. I smoke the AM regular double corona as a my day-to-day cigar and it is equivalent to a Monte in every comparison - flavor, aroma and fulfillment, but without the high cost factor. You may have to ask around some, but if you can get hold of one of these cigars, you will not have to consider taking a risk at trying to smoke an illegal Cubano - you will be doing basically the same thing - except doing so legally!