Continuity mistake: At the beginning, there is a scene where Ben spills a carton of milk. He picks it up right away, but a split second later the scene changes, the milk is still lying down, and he puts it upright again. (00:06:25)
Continuity mistake: Right before Capt. Ron tells Martin to put out the bumpers as they enter St. Haag, you see Martin running on the side of the boat. The camera angle changes and Martin is now standing right next to Capt. Ron and when he tells him to put out the bumpers, you see Martin running on the side of the boat. (00:26:05)
Continuity mistake: In the scene where Captain Ron walks in on Martin and Kitty taking a shower, she is behind Martin as he is facing the side of the shower toward the door handle and Captain Ron. Then, when Captain Ron walks over to the left side and the doubles fall out of the shower, they are facing Captain Ron suddenly, which is the other side of the shower, not toward the door handle. (00:35:15)
Continuity mistake: In the beginning, Martin gets a cup of coffee. After he gets off the elevator, he drops the coffee cup into the trash - but it clearly has never had coffee in it. (00:02:00 - 00:03:30)
Continuity mistake: When Kitty is scrubbing the deck with Caroline and Captain Ron turns up with the video recorder, Kitty is in the midst of putting on her yellow cleaning gloves and the scene immediately shows Captain Ron filming Kitty's behind while she is wiping her hands on the back of her jean shorts and Kitty has no yellow gloves on. (00:41:15)
Continuity mistake: When the two are on the boat discussing the carvings on the bed, Kitty's shirt is hanging over her shoulder. Without adjusting it, it is back to its normal place when they show her again. (00:58:55)
Continuity mistake: The dinghy moves around (at one point they play Monopoly on it), then it disappears, and reappears.
Continuity mistake: When Ben is playing Monopoly with the General, first a die is on the board, then it's gone in the next shot. Then, it's back where it started in the third shot. (00:32:00)
Continuity mistake: In the scene where the engine has just seized and they are putting up the sails, when they get them up, they are on a starboard tack, the next shot shows Caroline hanging on the starboard shroud but they are on a port tack, then a couple of shots later she is still on the shroud and they are back on a starboard tack. (01:29:00)
Continuity mistake: When Capt Ron is driving around Cuba trying to outrun the pirates, the mom starts off in the rear seat on the passenger side, then she jumps to the middle, then back again to the passenger side. Granted they are being flung around in the back seat, but the son switches positions with her each time and they are both sitting perfectly upright each time. (01:20:00 - 01:21:10)
Continuity mistake: In the scene where the Wanderer loses its inboard motor, just after the pirates begin chasing, the time of day changes very quickly, going from dark to dawn to daylight in a matter of seconds. Just after this, we are shown several instances of the pirates chasing the Wanderer in which the background islands go from non-existent to close up to mid-horizon to close up and so on. It is very hard to follow how far away the land is. (01:26:00)
Plot hole: After Captain Ron gets fired, Martin mentions seeing Roscoe. How does he know who this person is? This is the first time we've heard Roscoe mentioned in the film. Sure we are then shown that Roscoe is the pimp for the prostitute but how did Martin know who he was?