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.

Install the Unofficiall Wineskin Winery from the provided link. Turn on the 32bit execution boot argument by going into Recovery Mode and entering nvram boot-args='no32exec=0' into the terminal. Open Wineskin, click the '+' sign and scroll down to find the WS11WineCX64bit19.0.1 (the newest version with 64 and 32 bit support, at the time of writing). Vox Music Player for Mac is a fully functional alternative to iTunes that is pretty popular. The Vox interface seems pretty simple but it packs a lot of punch. This music player has the ability to play many different common formats including MP3, APE, M4A, FLAC, and CUE, so it is a great option if you have songs in your library that are not all the same format. Alternatives to Wineskin Winery for Mac, Linux, Wine, BSD, Android and more. Filter by license to discover only free or Open Source alternatives. This list contains a total of 15 apps similar to Wineskin Winery. List updated: 8:47:00 PM. Catalina 10.15.7 Catalina & Windows 10 Dual-Boot (clean install, on one drive): Boot into your Mac installer, Create 2 partitions in GUID table (1 for Win (I used FAT32 but I think it doesn't matter what you choose), 1 for Mac).

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.

PlayOnMac lets you download and run supported apps easily, but isn't good for just any exe.

CrossOver is paid software.

If all you want to do is run exes with right-click>Open With, than install WineBottler.

Nov 24, 2015 9:19 PM

Run Windows-based Programs on a Mac

Wineskin Alternative Mac Catalina Patcher

» News: Cryptographic Update for WineBottler 4.0.1.1

Turn Windows-based programs into Mac apps –
NOT. ;)

WineBottler packages Windows-based programs like browsers, media-players, games or business appli­ca­tions snugly into Mac app-bundles.
Your company provides you with a login, mail, calendar and contacts that only work on certain browsers?
You quickly want to test your websites in Windows-based browsers.
You want to play games, that are not ported to OS X?

Wineskin For Catalina

Your online trading platform or accounting tool only runs on Windows?
Your audio book player is not available on OS X?
No need to install emulators, virtualizers or boot into other operating systems – WineBottler runs your Windows-based programs directly on your Mac.
This is possible thanks to a Windows-compatible subsystem, which is provided by the great OpenSource tool Wine.

WineBottler does Automated Installations:

Select from a wide range of software for which WineBottler offers automated installations. It is as easy as hitting 'Install' – and WineBottler will leave you with a neat app on your desktop. WineBottler does not come with the programs themselves, but with scripts, that take care of down­loading, configuring and installing everything into an app for you.

WineBottler can pack your .exe into an Mac .app ...

Double-click your .exe or .msi and convert it into an app with WineBottler. You can run the generated app like every other program on your Mac. For advanced users, WineBottler gives you a selection of options: install special dependencies and even turn your .exe into a self-contained app - that is an app, that contains everything to run it... even on other Macs. Porting to OS X

How To Use Wineskin Mac

never was easier ;).
Find out more - have a look at the Documentation.

... or just run that .exe.

You don't care about generating an app and just want to run it? Double-click the .exe, choose 'Run directly' and Wine will run it in a generic environment.

Enjoy, it's free!

Like Wine, WineBottler is free software. We've made it out of our own needs and now we share the result. If you are happy with it, you can keep the project rolling by sending a small Donation.

Need other Versions of WineBottler or Wine.app?

We keep selected builds for you. Versions before 1.4.1 still run on OS X Tiger and Leopard.
You find them under Downloads.

Support

If you have questions installing a certain program, please have a look at the documentation or at appdb.winehq.org first. winehq.org is the hub for all info about wine. It contains notes, hints and tricks to install all major programs.
winehq.org is NOT affiliated with WineBottler in any way. So please do NOT post bug-reports or questions about WineBottler there - write an eMail to mikesmassivemess(at)kronenberg.org and if time permits, i'll try to get your exe running.
WineBottler is my hobby and it is free, so please understand, that I can't give you a one-to-one support. If you are looking for a Wine version with great dedicated support: Note down this Promo Code: 'TANGENT' (for a 30% discount) – then head over to CrossOver.