Does it involve your boat being confiscated?
Not this time. Hahahahaha
I was on my friend's boat. This is going back 15+ years. My friend had this connection down there and he wanted to make some cash hauling back cigars. He didn't want to go alone though... and he convinced me (with some of that cash) to go with him. He had a center console fishing boat similar to mine... not one that you would suspect in a cigar smuggling trip since it was like 100 mile trip there and 100 more coming back. You had to have a boat capable of getting there and back without refueling though.
Short version. Both times we left from Key West 1st thing in the morning. Appearing as though we were heading out offshore fishing. We had all the rods out and everything just like we would if we were actually fishing. Then we would head straight down to Cuba (on his boat it took about 5 hours). GPS took us directly to our connection there. Just a crappy dock that was falling apart behind two old houses. He did the business part and I just stayed in the boat. Then we loaded those cigars in every single compartment he had on that boat. It took about an hour for us to load em all in. We also got some real Cuban food and rum from his guy.
Then,,, we would head back across but at a much slower pace than we came over in. We ate, drank, and slow trolled our way back over. We always wanted to get back to the boat ramp when it was dark and as late as possible. We never caught any fish either time btw LOL.
Both times we got back to the ramp real real late,,, put his boat on the trailer,,, and drove back to Melbourne, FL with the boat filled with cigars dragging behind us. Those were the only 2 times he ever did it... but the funny thing was that we would find cigar wrappers for years after in the weirdest places on his boat when we were just out fishing... sometimes they would just seem to fly out of nowhere.
He made some nice money doing it, but both of us cringe now about how stupid we were to go do that. His connection was really really good and we knew that,,, but damn we were some dumbasses.