DosBox will let you play the dos based games. For windows proper, meaning 688 h/k, SubCommand and Dangerous Waters, you will need something like Parallels or VMWare. Both of them in their current versions will play 688 and SubCommand with no problems, but DW has problems with the 3D engine that fails to properly render models. If you can live without the 3D graphics (and as a hardcore subsimmer you don't use the external camera anyway, right?) the two virtualization systems will let you play DW.
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