"Carribbean Tales" and "City of Abandoned Ships" are badly affected with bugs.winehq.org/show_bug.cgi?id=27439
I looked at the wine bug report and honestly was amused because those same bugs happen in windows as well. The mods fix many of these problems and I would be very interested as I do not run a linux partition right now myself, how wine will run the game with mods added. I would highly recommend you try my stand alone version of this game available from BuccaneersReef dot com. Its called Gentlemen of Fortune ERAS and runs on a new proprietary engine called MAELSTROM. It is virtually bug free on windows so I am wondering how it behaves running on wine. Perhaps I should build a linux partition again in VMware on my main PC again so I can try it myself.
My experience running it on Windows was not so bad, regarding the "crashes while entering the sea" bug, actually, I guess I never saw a crash of these games on Windows with that particular bug.
However, with Wine, it's crashing every time. Clear game (downloaded from GOG), no mods, even at fresh new game start.
I might give a try to those mods one day. ;)