Sid Meier's Colonization

As fun as it was as a kid first learning to play games.

If you're looking for cutting edge graphics you're in the wrong place. But if you're looking for a great simulation of the new world & revolution from a civilization-style perspective then look no further. This game is significantly better than the modern remake (Civilzation 4: Colonization) and has several features that Civilization did not, perhaps the most important of which is the management of your colonists. Each colonist has some specialty (or no specialty) and works most effectively in that role; managing and acquiring/training those specialists is a key factor in the game and is quite enjoyable. You can find this for free and play it with dosbox on your own, but if you're not more technically inclined it's definitely worth the price of admission here on GOG.

I was hesitating, but the two previous comments convinced me, I'll get this right away!

This is definitely worth your time, however be prepared to work around the problem with combat, which is severe enough that it can ruin in minutes a well-played game that you spent many hours putting together. The combat problem is that the actual odds in combat bear no resemblance to the odds given by the game. You'll commonly encounter astronomically-improbable battle outcomes, and mostly these will be quite bad for you. At times, the game seems to decide that certain units will not be defeated, and anything you send against them will fail, no matter how many units you have at your command. My experience is that this can be worked around to some degree by choosing different attack squares or changing to a different attack then changing back (things that may give you a new roll of the random number generator), but probably you'll need to resort to save-scumming when this happens. Five stars as a simulation, minus one for a crippling problem with a key game element.

I recently discovered Colonization, and found it to be a really good game that does not feel aged. Of course the graphics are simple, but they could just as well be from a modern retro-style game.