Jan 20, 2011 CrossOver has a GUI for installing Wine does not. CrossOver is more a tested version fork of Mainline wine. Tested to work with a particular list of applications and freases there. By the way CrossOver Linux other than the GUI that is closed source the complete wine source code used in it is down-loadable and you could choose to build it yourself.
Note: I know this is an old thread, and am just posting to help anyone else who stumbles upon this thread.
First of all: Wine (just plain wine) is NOT available for Mac, so that leave you with Wineskin, WineBottler, PlayOnMac, or CrossOver.
Wineskin and WineBottler are intended for creating wrappers, which is basically converting it to a Mac application.
Wineskin gives you more customization over your wrapper.
WineBottler also comes with a system that lets you just run any exe on mac just like that.
Wine Vs Crossover Mac
PlayOnMac lets you download and run supported apps easily, but isn't good for just any exe.
Crossover Mac Free
CrossOver is paid software.
Xquartz
If all you want to do is run exes with right-click>Open With, than install WineBottler.