First, remember that the night before Jack Kennedy signed the executive order that instituted the embargo with Cuba, he sent Pierre Salinger out to the best tobacconists to buy him a thousand cuban cigars. Didn't tell him why he needed the thousand. Pierre came back with 1,200. i know it was just recalled on the West Wing, and it is absolutley a true story and not urban legend.
So in terms of violating the trading with the enemy act, which includes bringing back cuban cigars, honestly, a tourist with a personal stash of cubans is NOT who customs is after--customs is after the wise-guy with a boat load or a trunk load driving across from canada (yeah, effective embargo, huh? CANADA won't abide by it--no one does). I've stuffed the cubans, ziplocked, into the zip pocket of my shaving kit, and even in a zipped inner bag inside DW's bag (she didn't know so her "poker face" was quite natural!).
Only time I got a box was from Windsor Ontario, right across the bridge from Detroit--called in advance, charged 'em to my visa, drove over, and in those pre 9/11 days a domestic flight did not involve the bodily cavity search that is required today thanks to terrorists, so it was not an issue to have them in my luggage for the flight home.
Front street in St. Maarten has several good quality tobacconists, with walk in humidors, visit a few, compare what they have in stock and what their pricing is, and get what your budget allows. It has been years, and I gave up my infrequent indulgences altogether when DS became old enough to ask about why I would smoke (2-4 cigars a year wont kill anyone, but it as a small sacrifice for me that made a big impression on him), so I don't know current prices. But the answer is yes--the price you see is PER CIGAR, not per box!! Ah, contraband...