Let's list the pros and cons of each version.

I've played all three versions. IMO, the Gold (1993) version is superior to the original (1987) in every way: they are basically identical but the Gold added better graphics and improved user interface. However, I like the Enhanced Remake (2004) version the best: it added some new features that were not in the original nor the Gold version.

The biggest pro of the Enhanced Remake version: players can see other ships sailing on the seas/world map. In the original and Gold version, players could not see other ships on the world map, so encounters were completely random and would suddenly pop out of nowhere. IMO, random encounters that do not appear on the world map and simply pop out of nowhere are the worst kind of encounters, (i.e., it was one of the main reasons why I despised Final Fantasy 7 so much.)

In the 2004 version, players can see other ships moving around on the world map, so players can either approach or avoid other ships and encounters. (i.e., the game has upgrades that can improve visibility on the high seas/world map; the various item/ship/specialist upgrades are additional features that were not in the original or the Gold version.)

That, IMO, is the single biggest improvement over the original and Gold versions, and it makes the gameplay so much more manageable and enjoyable.

2004 Cons: Ridiculous dancing sequences. Lengthy swordfights and plundering of cities. Sneaking into a town was also absurd.

In every way but one: I remember when I first played Gold, I was a bit - a very little bit - disappointed that you didn't get carreer specific illustrations when you retired. You could get three or four different ship illustrations, based on your station. But in the original, you got an illustration of yourself in whatever profession you ended up in, which is something I was glad to see they brought back in '04. Perfectly trivial, but still. Why is plundering cities a con in the 2004 version? Plundering cities was a hopeless affair in the original '87 version, and still awkward and clumsy in Gold. In the '04 version, you have a much better overview and also - more importantly - controls you could easily comprehend. I also love the fact that they made it turn-based.

1987/Gold Con: Swordfight flailing. Theoretically you had all your block directions, but good luck at interpreting and timing it correctly. The animation was confusing. Opponents attack so fast that you'd need to train with a stopwatch like an Olympian to get good. It's out of sync with how easy the other aspects were to get into.

1987 Con: Sun sighting. Clever, but.. ugh.

1987 Pro: Retirement professions that weren't bizarre. In the 2004 version, we have Fencing Master, Butler, Bishop, Mortician? Uh, ok.

Gold Pros: The realtime land battles when attacking towns were neat. Marrying a merchant's daughter.

2004 Con: Disney/Pixar/The Sims theme. I don't mind it too much, it's just way too cutesy and overblown. After knocking out 9 pirates with a conveniently placed crate, you'd think the 10th would catch word and not hang his cargo in the exact same spot. You'd be wrong.

2004 Pro: Swordfights with a degree of strategy. Crew, ship, and personal possession upgrades. Pirate-O-Pedia (so nice!). Treasure hunting via landmarks. I think this version has the best all-around gameplay. And I'll get some hate, but I like the dancing!

I thought I'd chime in on this, since I originally felt the same way. I started out years ago with the Genesis/Mega Drive version of Gold, and hadn't played it for years until I tried the 2004 remake.

When I went back and started playing the DOS version of Gold, I was really lamenting this. But now, when I want to play Pirates!, I usually run straight for Gold. Let me try to explain why...

Think about it - in 1660, there was no electronic technology. Sailing at night, in storms, etc, a ship would have had no clue another ship was nearby until it was directly upon it. Although the ships not being drawn was likely a technical limitation of the time, it also has real gameplay value. Although it can make the game feel really "lonely," it creates that sense of isolation and concern of the unknown that sailors at the time probably had.

One thing I really miss in 2004 remake is the Captains Cabin. Although purely aesthetic, the cabin kind of seemed like a "refuge" when you were out on the open sea. Although all of the same options and information is available in the 2004 remake, via a typical menu screen, the cabin is part of what created some of the nostalgia for me with Gold.

Although I love all versions of Pirates!, and have probably put the most time into the 2004 remake, I'm finding an entirely new magic with Gold and I think that feeling of isolation has a little to do with it. I just wanted to throw that out there for those who have not played these older versions.