One of my good friend's father is, well, quite rich and has a 56' yacht and he took five of us once when we were 18/19 on a Bahamas cruise that sailed through Nassau/Paradise Island for the last three nights (and a lot of other awesome small island stops). First night we were there we all decided we were going to play some blackjack, and, well, the cards were not with us that night. We convinced the floor manager to open us up a table and in about 45 minutes to an hour, between the five of us, we'd lost about $800 total.
Next night, one of said friends was belligerently drunk at a table and was egging people on saying things like "THE COUNT IS HIGH, BET IT ALL!" to people and urging people to double down as they were trying to play their hands. The rest of us were just standing and watching but he got us all kicked out.
I did at least see Patrick Ewing and his family there (they had a monster 120+' boat) and had him autograph a twenty dollar bill for a die-hard Knicks fan friend of mine.
Another friend shacked up with a girl at the hotel on our last night, knowing we'd be leaving early in the morning, like 5AM for our return trip. It got to about six and we decided he was on his own so we went ahead and fired up the engines and prepared to depart, we were untying the lines to the boat as he came stumbling up. He was literally about 10 minutes from being stranded in Nassau and having to buy his own plane ticket home.