You should have good success. You can use Wineskin for the later Windows-based games.

Over the last couple of years I have played MM1-8 and HOMM1-3 on my Mac. I'm not using the GOG versions (I still have my old discs), but it shouldn't be too different.

I used to play on my Mac, but the problem was installing it. You couldn't just unzip the installer as it led to a nesting doll of infinitely more .exe files. Setting up required first getting the installed files off a PC, but once you have DOSBox running it works like any other game.

Thanks folks. I can probably install it to a windows machine first and transfer the installed directory over to the mac. Glad to hear that there's some success along this front.