Just went to Ybor city last weekend. Place is a ball! Tampa Sweethearts is probably the best of the lot, but I admit that we only hit 8 or so shops. Most of the small cigar shops we saw seemed to have pretty much the same thing. Only bought one freshly hand-rolled and it was honestly horrible!
We missed a few Ybor area cigar shops and plan to road trip again to hit those, along with a visit to Cigar City Brewing co. That place is simply amazing!!! More beers on tap than should be allowed and a great selection at that! We hit a small local place to eat (Tropicana) on 7th and the frijoles negros & café con leche were superb!
There are several more cigar places in Tampa as well. You all could do Busch Gardens and the Florida Aquarium. Also a place over there known for smoked fish is Ted Peters.