Best way to run WINE on OS X?

What is it?

(I know, oh so subjective.)

So let's make that, what's the most effective and pain free way to do it? I realize those may be contradictory conditions.

The easiest and most pain free way is to use homebrew

https://github.com/mxcl/homebrew

Once you follow the instructions to install homebrew on this page (which include installing Xcode), you can then simply type

brew install wine

And this will download and compile wine and all its dependendencies.

You can install wine using MacPorts or Fink they both are recommended my wine.

As for GUI applications for wine the only thing besides wine's own utilities is winetricks. They are pretty useful for automatically downloading and installing different applications and dlls with their dependencies.

If your OSX is older than 10.5 than you will definitely need to install XQuartz (newer version already include X server).

MacPorts

Let's search packages matching 'wine':

port search wine

wine @1.4 (x11)
    Wine Is Not an Emulator

wine-crossover @11.0.0 (x11)
    Wine Is Not an Emulator (1.4-rc5 with CodeWeavers modifications for CrossOver)

wine-crossover-games @10.1.1 (x11)
    Wine Is Not an Emulator (1.3.9 with CodeWeavers modifications for CrossOver Games)

wine-devel @1.5.0 (x11)
    Wine Is Not an Emulator

winetricks @20120308 (x11)
    downloads and installs various redistributable runtime libraries

Now we see that we can either install CodeWeavers version or just usual wine. Let's install usual wine (I think that for another one you need some kind of licesce):

sudo port install wine

It's also a good idea to install winetricks:

sudo port install winetricks

Fink

Install Fink as deskribed here.

fink list wine

     wine                  1.3.21-1         Microsoft Windows compatibility layer
     wine-dev              1.3.21-1         Microsoft Windows compatibility layer
     winetricks            20111120-2       Install redistributable runtime tools in Wine

Let's now install them

fink install wine
fink install winetricks

After installation

In terminal enter wine and press [Tab] and you will see utiles that come with wine (and winetricks of course):

wine         winebuild    wineconsole  winedbg      winefile     winegcc      winemine     wineserver   
wineboot     winecfg      winecpp      winedump     wineg++      winemaker    winepath     winetricks

winecfg is very useful to configure wine (dlls overriding, Windows version selection, etc.)