Help me find a few games from my childhood (GA)

I've remembered a few games from my past, and I would love to play them again, but I just can't remember the names.
The first one is a 2d game about pirates. You had your ship and you went from town to town doing quests and stuff. You could encounter other pirates too. Each city had a bank, a dock (or harbor,can't remember), and a mayor (?) who gave you quests(and maybe a few more places). You could visit other cities by going to the map. The map was middle america (belize, trinidad and tobago....) and you could also upgrade your ship and other stuff. Oh and the characters were only faces, so if you went to the bank, you would only see his face, and next to it was a box in which you typed the ammount you borrow/deposit.

The second one is a puzzle/adventure game. It's 2d, and all I can remember is that one of the first puzzles was something about going to your mailbox, and in there changing some letter or something. Little to go on, I now, but I can't remember more

The third one is a side-scroller, the main character was this cat that looked like a captain and you could use a gun,dynamite, a sword and magic. You fought dogs dressed as guards in the first few levels. You could also get treasure and stuff.
Hope you can help me out! Helpful people will get a steam emoticon from me!

edit:
The first one is Tradewinds

I still have no clue what the second one is

The third one is Captain Claw

Thanks to all who helped, still waiting for the third one

Here's another game I enjoyed playing!

edit 2:
For the second game, I think I remember it's icon being like a arcade cabinet or some machine, but I'm not sure