If you are going back to the USA
then you do not want to buy anything from Cuba--especially at the airport.
Next, if you are in Santo Domingo, one of the best places to buy cigars is right next to the Metro station near Winston Chruchill Ave. The is a cigr store in Hotel Lina that is good.
If you come to Santiago, you can visit a factrory or two...this is where they are made.
US allows you 50 cigars as does Canada. You can take more but you run a small risk.
HB, cigar guru!! Hahaha Well, it's true!!