The Tradewinds games are remakes and spin-offs of Taipan, a game written by Art Canfil for the Apple ][. It had a basic interface and reasonable graphics (for its time). Since then, the simple yet addictive gameplay of trading commodities and fighting pirates has spawned various remakes.
The Tradewinds franchise owned by SandLot Games is one such remake. It added period art, and in subsequent games changed the geography; and added magic, mythology. The addition of character stories and quests of increasing complexity and story-telling has also made them a type of fantasy role-playing game.
Tradewinds Classic is a simple remake, adding fun, colourful artwork and character biographies, and varying the game experience with different starting resources for different characters. In terms of fantasy elements, however, there isn't much here.
Tradewinds 2 expanded on the idea and added more detailed stories for characters by introducing tasks and a story arc for the character, interwoven with those of the other playable characters. Pursuing the character's story is optional, and even after a character's story ends, you can keep playing and amassing a fortune. Tradewinds 2 also began introducing a fantastical element with such things as using voodoo to help you in sea battles.
Tradewinds Legends took the Tradewinds franchise to an all-new level of fantasy, incorporating genies as a race regularly encountered and flying ships to visit ports high above sea level. Magical events and artifacts abound, and character stories were improved to be much more interesting and different for each character. The game had a spinoff, Unlikely Heroes, featuring new stories and new commodities, but essentially the same gameplay.
Tradewinds Caravans toned down on the magic somewhat, but in graphics and especially in character stories, it improved considerably over Tradewinds Legends. The action moved away from sea to land now, along a mythical Silk Road, and travel now allowed players to manually avoid encounters rather than running into pirates and choosing the flee option.
After a somewhat complicated and more hands-on experience in Tradewinds Caravans, Tradewinds Odyssey was a return to the more familiar sea-travel format, this time in the Greece of mythology, and followed the structure of Tradewinds Legends quite closely. The storytelling is the best yet by far, with a mix of the comic, the serious, and even the philosophical. And for the first time, the game tracked a player's progress across various games, awarding feats and a point score reflecting how much of the game (as opposed to an individual story) had thus been discovered.