Orbiter Space Flight Simulator uses Direct3D (7) and so is not strictly compatible with any operating system other than Windows. However, using Wineskin Winery, it is not too difficult to install on Mac OS X. For this how-to, I’m using Mac OS X Mavericks, Orbiter 2010-P1, and Wineskin Winery 1.7. I could simply supply the Wineskin Wrapper I’ve made here for you to download (minus Orbiter, which I wouldn’t be allowed to distribute without permission). Instead, however, I think it is useful to more people to learn how to actually set up software using Wineskin.
First, download Wineskin Winery. Then, download the Orbiter 2010-P1 MSI Installer from here.
Launch Wineskin Winery. Note the installed engine in the list, then click the + button. Check to see if there is a later (high number) engine available, and if so click Download and Install. Then, click “Create New Blank Wrapper.”
Next, type your desired application name. I chose “Orbiter2010-P1.”
Give Wineskin some time to work its magic, at which point you’ll see this:
Click OK. Now, go to your launchpad to find the app, or else under /Users/YOURUSERNAME/Applications/Wineskin/. Click “Install Software.”
Now, click “Choose Setup Executable,” then browse to your Downloads and select the Orbiter MSI installer.
You’ll be greeted by the Orbiter installation.
Click next, agree to the terms, and and not the next screen, select “Custom.”
For some reason, the default install location doesn’t mate well with Wineskin, so after Location, select “Browse.”
Under folder name, replace the text with “C:\Orbiter2010\”
Click OK, and then click Next through until completion of the installation.
Wineskin will ask you to choose the appropriate executable (since there are a few in the Orbiter folder). In the drop-down menu, select “/Orbiter2010/orbiter.exe”
You’ll next be presented with the Wineskin configuration screen. Select “Set Screen Options.”
You might be tempted to select “Override” and then the “Fullscreen” option. Don’t. it’s nicer to have the Orbiter launch panel show up in a Window; then we’ll set Orbiter up so that it is fullscreen. Select “Use Mac Driver instead of X11,” and then I also selected the Direct3D boost, but I’ve no clue if it actually does anything.
Click “Done”, select “Quit” and then run your Orbiter app again. Now, instead of being presented with the Wineskin menu. Orbiter will launch. The first time Orbiter is run, it will do a serious of checks and will fail on the Direct3D check; however, the program still appears to work. There is a strange flickering effect if we were to leave things the way they are. So go to the “Video” window, and select the 3D device dropdown menu. Instead of the default “Wine D3D7 T&L HAL (Direct3D HAL), select “Wine D3D7 RGB (Direct3D HAL).” Also, select the “Full Screen” button, and set the resolution to whatever you’re running. (Note: Wineskin Winery I do not believe supports the Mac’s retina resolution, and so here I’ve selected half of it, 1440×900.)
Ok, that’s it. Either click “Exit” or select a Scenario and “Launch Orbiter.”
That’s it. Now you’re playing Orbiter on your Mac.

Except, you may notice that you are now unable to control your spacecraft, since by default Orbiter utilizes the Windows number pad. There are a couple of options. You may simply assign any alphabetical keys you want to the control of the spacecraft, or preferably, hook up a Mac number pad. Unlike Windows, however, the keys are not NUMPAD keys, but rather just the numbers themselves. In other words, in Windows, 4 and NUMPAD4 are two different things. In OS X, they’re the same. Therefore, it is necessary to modify the keyboard configuration file in Orbiter to recognize these numeric keys. Right click your Orbiter app and select “Show Package Contents.”

Now, you’ll see the “contents” of the wineskin package.

Click on “drive_c”, select Orbiter2010, and find the file called “keymap.cfg.” Open it in your favorite text editor.
Now anywhere you see NUMPAD, simply remove that text to leave only the number behind it. A simple search and replace will work just fine.

Additionally, you’ll also want to find the line for “DecHoverThrust” and change “DECIMAL” to “PERIOD”. Now, when you start up an Orbiter scenario, you’ll find your numpad works.
If you’re only interested in getting Orbiter installed you can stop reading here, but there are a few things you can do to improve the experience. So if you’re interested, continue on.
Orbiter 2010 is a bit dated graphically at this point, so go to the “Visual Effects” window, and turn on options as desired; more than likely your Mac will have no problem handling it.
The default textures in Orbiter are relatively low, but higher resolution textures are available. Return to the Orbiter Forum download page and scroll down to the Optional Texture packs section. Get any or all that you’re interested in (at the very least, download the high level 14 Earth). If you’ve downloaded all these resolution packs to a single folder, then when you open it, it may look something like this:
Double click each zip file and they will extract to sequentially numbered “Textures2” folders. Combine all the files from these folder into a single “Textures2” folder. It may look like this:

Select all these files and copy them. Now, we must place the contents of this folder inside the Orbiter directory inside the Wineskin wrapper. Open the Finder and navigate to your home applications folder (Click Finder, then Go >> Home, then double click “Applications” and finally “Wineskin”). Right click your Orbiter app as you did earlier and select “Show Package Contents.”
Launch the Wineskin application located here. Note that for any other addons you may ever want to install in your Orbiter wrapper, this is how you’ll do it. Now simply navigate: “drive_c” >> “Orbiter2010” >> “Textures2.” Now paste the clipboard content in here. The higher-resolution textures will now be used next time you launch Orbiter.
Another practically essential add-on for Orbiter is Dan Steph’s Orbiter Sound package. Download it from here. Since this add-on is an installer, the procedure is a little different. Navigate again to your Orbiter app and show the package contents. You’ll see an app here simply called Wineskin. Launch it. You’ll be greeted again by the Wineskin settings window. Note for the future that this is where you’ll go if you ever want to change any of the wrapper settings. But for now, click “Install Software” and then “Choose Setup Executable.” Select the Orbiter sound installation file.
Click “Browse.” Expand the “/” directory, then “Users,” “YOURUSERNAME,” “Applications,” “Wineski,” “Orbiter2010-P1.app,” “drive_c”, and finally click “Orbiter2010.”
Click “OK” and then “Install OrbiterSound 4.0.”
Once done installing, you can choose to run the configure tool and set it up however you like.
Next time you launch Orbiter, you’ll now have sound.
