Buying a Cuban Cigar in Cuba is a tricky business.
There are no end of people who can roll a ?professional? cigar.
When you buy Cigars on the street you pay extra for the box, the stamp, the hologram, the ?official? receipt. And (of course) if your a novice you just over pay.
I have met people who work at Government run Cigar stores. They bring in boxes of locally rolled cigar dressed up to look real.
Tourist have no idea what they are buying.
It is really, really, really hard to buy a REAL high end Cigar, in Cuba.
When I am there I do one of two things.
1) I go to a Cousin-in-Law and describe the Cigar I want (as long as a pencil but thicker) and tell him I want his best tobacco, no box, to stamps, just wrapped in paper.
or
2) I buy the Cigars, the Government sells, and real Cubans actually smoke. They are about 6? long and 3/4? thick. They costs $1 for 25cigars (yes, 4 cents each). I used to buy 50 cigars and take them home for my Son (in University) to sell to other Students for $10 each. My Son was always happy when I got back from Cuba.
I am positive Cuba sells the best Cigars, but good luck finding one.