CrossOver
One-click local install, official support.
Difficulty: MediumCost: $74 one-time / $39/yearGood
CrossOver
How to play Monkey Island 2: Special Edition on Mac
Adventure · 2010
Plays smoothly through CrossOver on Apple Silicon.
Overall rating: Not enough votes yet
Your setup
Detect your Mac to see whether Monkey Island 2: Special Edition will run.
Plays smoothly through CrossOver on Apple Silicon.
How to run Monkey Island 2: Special Edition on your Mac in 2026
Best path: CrossOver
CrossOver runs Monkey Island 2: Special Edition natively on Apple Silicon by translating DirectX to Metal. One-click install, no Windows VM, full local performance.
Monkey Island 2: Special Edition
LeChuck's back and Guybrush Threepwood is determined to find the legendary Treasure of Big Whoop. This remastered classic adventure features sharp humor, challenging puzzles, and a memorable story set in the Caribbean.
This remastered classic adventure plays perfectly on Apple Silicon via CrossOver or Whisky.
What the world thinks
Performance
How Monkey Island 2: Special Edition runs on your Mac, from our performance model and player reports.
See exactly how Monkey Island 2: Special Edition will run on your Mac
Pick your chip and RAM for a personalised estimate.
Best way to play it on Mac
This remastered classic adventure plays perfectly on Apple Silicon via CrossOver or Whisky.
See if this is the right method for your setup
Ways to play Monkey Island 2: Special Edition on Mac
Here are all the options available, ranked by what we recommend first.
Parallels
Full Windows 11 ARM inside macOS.
Difficulty: MediumCost: $99/year + Windows licenceEstimate
Whisky
Free option built on Game Porting Toolkit.
Difficulty: MediumCost: FreeEstimate
Compare methods at a glance
Lower = betterHow each supported method stacks up on setup effort, time and runtime overhead.
Method
Setup Difficulty
Time Investment
Performance Overhead
- CrossOverTranslationTop pickSetupModerateTime15 minOverheadMedium
- WhiskyTranslationSetupModerateTime15 minOverheadMedium
- ParallelsVMSetupModerateTime30 minOverheadHigh
Where to buy Monkey Island 2: Special Edition
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Step-by-step setup guides
Idiot-proof walkthroughs for every method.
How to run Monkey Island 2: Special Edition on Mac with CrossOver
Good· CompatibilityRunning Monkey Island 2: Special Edition through CrossOver translates its Windows DirectX calls into Metal on Apple Silicon — no reboot, no Windows license, no virtual machine. Most setup time is spent on first-time bottle configuration and installing the game launcher (Steam, Epic, etc.) inside CrossOver. Once that's done, launching feels close to native. Expect 15–30 minutes of setup on the first run.
Step-by-step
Step 1 — Create a bottle
- Open CrossOver → click New Bottle
- Name it after the game (e.g.
Monkey Island 2: Special Edition) and choose Windows 10 64-bit - Open the bottle's Settings and set:
- Graphics: D3DMetal (not DXVK)
- Synchronization: ESync
- High Resolution Mode: Off
Step 2 — Install the game launcher
- Inside CrossOver, click Install Application → search for Steam (or Epic Games Launcher if you own it there)
- Install it into the same bottle you just created
- Launch Steam, log in, and let it fully update before proceeding
Step 3 — Install and launch Monkey Island 2: Special Edition
- Open Steam (or your launcher) inside CrossOver
- Install Monkey Island 2: Special Edition through the launcher as normal
- Launch the game — use the launcher's Play button, not CrossOver directly
- First launch may take 30–90 seconds to show a window. Don't force-quit unless it hangs for several minutes.
Step 4 — If you hit issues
- Black screen / stuck in small window: go to Settings → Graphics in-game, set Screen Type to Fullscreen, then restart
- Resolution resets on every launch: find the game's config/settings file and set the resolution values manually, then mark the file Read-Only to prevent the game overwriting it
- Crashes on startup: try switching the bottle's Synchronization from ESync to MSync, or vice versa
Video proof
Try CrossOver free for 14 days ↗Affiliate link — supports the site at no extra cost.
How to run Monkey Island 2: Special Edition on Mac with Parallels
Estimate· CompatibilityUsing Parallels to play Monkey Island 2: Special Edition means running a full copy of Windows 11 ARM inside macOS. This is the most "it just works" approach for games that don't behave under CrossOver, and DirectX 11 is hardware-accelerated. You'll need a Windows license and roughly 80 GB of disk space.
Step-by-step
- Buy / start a trial of Parallels Desktop.
- Install Windows 11 ARM via the one-click wizard.
- Inside Windows, install Steam / Xbox app and Monkey Island 2: Special Edition.
- Enable DirectX 11 in Parallels settings for best 3D performance.
Video proof
Try Parallels Desktop free ↗Affiliate link — supports the site at no extra cost.
How to run Monkey Island 2: Special Edition on Mac with Whisky
Estimate· CompatibilityRunning Monkey Island 2: Special Edition through Whisky translates the game's Windows DirectX calls into Metal on the fly. Performance is impressively close to a native Windows PC on Apple Silicon, and you stay entirely inside macOS — no VM, no rebooting. Expect to spend 10–20 minutes on first-time setup.
Step-by-step
Video proof
Download Whisky (free) ↗Affiliate link — supports the site at no extra cost.
Our recommendation
For most Mac players we recommend CrossOver as the fastest, smoothest way to play Monkey Island 2: Special Edition. One-click local install, official support.
| Method | Quality | Difficulty | Cost |
|---|---|---|---|
| CrossOverPick | Good | Medium | $74 one-time / $39/year |
| Parallels | Estimate | Medium | $99/year + Windows licence |
| Whisky | Estimate | Medium | Free |
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