As a first time Habano smoker/buyer, I suggest something from the Duty Free. If you don’t buy at Duty Free, there is a cigar store on calle 7; exit Hotel Presidente, turn left, walk to corner, turn right across Avenida Central and walk most of a block uphill. On your right will be a tobacco shop.
Counterfeit Cuban cigars are abundant in San Jose. The one place without a doubt has the real deal is at the only Licensed (LCDH) Cuban Retailer in San Jose -
http://www.habanoscr.net/.
As far a cigar choice/type, the Monte Cristo #4 or #5 (somewhat smaller corona) is always a good choice or if you want a big “look at me†cigar, the Monte Cristo #2 (torpedo) is not a bad choice. A good solid choice would be an H. Upman, Magnum 46. Last time I stopped by the little shop close to the Presidente, they had the Mag 46 (corona gorda). Another good solic choice would be a Partagas, Series D, #4 (robusto.)
Habanos are typically a little stronger; deliver a little more vitamin nicotine than others. Me, I love a good strong, “in your face†cigar.
My opinion on cigars is similar to my opinion of sex and whiskey. “It needs to hurt a little bit to be any good.â€