Luckily, it is not difficult to get your playlist across the cable to your phone. Here are four ways that you can use to sync iTunes music to Android.

1. Sailing Media Sync

Sailing Media Sync can sync your iTunes music, playlists, podcasts and photos from iPhoto or Aperture onto your Android device. It is currently available in two versions: free and premium. The free version copies all your media files every time it performs a sync. It does not keep a record of what has already been sync. Depending on the size of your media library, the whole syncing process can take a long time. On the other hand, the pro version costs $22 and it can intelligently updates your phone, resulting in a faster sync. The usage is simple. Plug in your Android device with the USB cable and turn on USB storage mode. Sailing Media Sync will automatically detect the device and prompt you to perform a synchronization. You can select from the list whether you want to sync music, podcast and photos.

Sailing Media Sync is available for Windows and Mac. Download Sailing Media Sync

2. iTunesMyWalkman

iTunesMyWalkman is a open source application that helps you to synchronize the contents of iTunes playlists to your mobile phone or other portable device, including Android phone.

There are several advantages in using iTunesMyWalkman.

  1. It works on Mac 10.4 Tiger. Most applications only work on Mac Leopard and above, so it is good to see that iTunesMyWalkman plays well with Tiger too.

  2. It includes iTunes scripts and Folder Actions so it can automatically detect your Android phone and synchronize your music and playlist right within iTunes.

  3. It is able to re-encode your music on the fly to save space. This is useful if you have a small storage space in your phone, or that your phone does not only support the media format in iTunes.

  4. It is able to sync your camera pictures to your hard disk or iPhoto. Note: If you have a large media library, it will be very slow the first time you perform the synchronization. iTunesMyWalkman is available for Mac Tiger and above. Download iTunesMyWalkman

3. Dazzboard

Dazzboard is different from all other apps. It is a web app that works within your browser (Firefox, Chrome, Internet Explorer, Safari). Before you can use it, you have to download and install a plugin from the Dazzboard site. After the installation, you can visit the website again and it will prompt you to launch the web app.

Within the app, you can select the music/video/photo/playlist from either device (your computer and Android phone) and transfer to and fro from each device. in Windows, you can even sync your Android applications to your desktop.

Dazzboard is available for Windows and Mac. Download Dazzboard plugin

4. DoubleTwist

This article won’t be completed without DoubleTwist. DoubleTwist is a great media player that many even touted it as the “iTunes for Android”. After you have installed it in your computer (Windows or Mac), it will automatically import your iTunes music and playlist. When you connect your Android phone to your Mac, it can detect your phone and give you an option to sync your media content.

Double Twist is available for Windows and Mac. Download Double Twist

Premium software

While this article is about free tools, there are several premium apps that can sync iTunes music to your Android phone as well.

  1. TuneSync – TuneSync allows you to sync your iTunes playlist wirelessly. There are two parts to TuneSync, an Android app and a desktop app. The Android app costs $4.99 (there is a lite version though) while the desktop app is free to download. TuneSync works on both Windows and Mac.
  2. iSyncr – Other than the usual syncing, iSyncr also supports smart playlist, song ratings, play counts, podcast and videos. iSyncr also comes in two parts: Android app ($2.99) and a desktop app (free). iSyncr is available for Windows and Mac
  3. The Missing Sync – At $40, this is one hell of an expensive app. However, it is also the best synchronization app out there. Things it can sync include calendars, Fliq notes, SMS messages, contacts, music, photos, videos, docs, podcasts and call history. It also supports wireless sync. What do you use to sync iTunes music to your Android phone?