Buying cigars in Cuba is one of the musts for a traveler that is interested in bring back home a genuine souvenir from the island. When comes to Cuban cigars there are several brands, sizes, and shapes. If you are not a cigars connousieur we will strongly recommend to take a look at Cuban Cigars History for information regarding the several Cuban cigar brands.
Once you are sure what brand and model of cigar to purchase, you will have two options regarding where to purchase them:
Buying your cigars in a Store, or Cigar shop:
The cigars that you will purchase in the stores and gift shops are mostly originals (sometimes the people that works on the stores introduce their own cigars boxes to make some extra money). In general originals or fake you those cigars are usually in good shape (they will not want to jeopardise their jobs selling you low quality cigars).
The prices in stores are always very high (mostly compared to black market cigars), but usually lot less than outside Cuba. The good part of buying in a store is that they can provide you a valid voucher for customs when you leave the country, this is important if you want to take more than 2-3 boxes
There are several stores in Havana where you could purchase Cigars, we have a list of the best places here: Havana Cigars Store [LINK].
Buying the cigars in the black market
Black market buying, on the other hand, is a real hit or miss process when it comes to cigars. There are two types of boxes: the ones that are stolen or somehow extracted from the factory (these are the less probable to find), and others that are just re-labeled cigars or just a counterfeit production. It seems all the cigars are in the right boxes, and all of them come with the appropriate stickers and stamps. It is important that you look for uniformity in color and size, and smell as fresh tobacco.
Everyone in Cuba knows someone who has access to cigars. Ask a person you can trust, like the bus driver or the house owners. If you've got a continuous relationship with them, chances are they won't sell you crap. The guy on the street who asks you to buy his boxes, however, doesn't care what he sells you because he'll probably never see you again.
Twenty-five through thirty-five dollars was the going rate per box when we were in town. Anything more, and you're being ripped off, anything less and you should question the quality of the cigars.