1. Setting the stageFirst, make sure you're running the latest version of
iTunes on both your Mac and your PC.
2. If you have an iPod, make it cross-platformJust
because you've brought a Mac into your home, doesn't mean your old PC
is chopped liver. You never know when you may want to sync your iPod
back to your PC, just for old time's sake. This step will allow you to
sync your
iPod
to both your Mac and your PC, without any hassles. To do this, connect
your PC-formatted iPod to your Mac. iTunes will launch and present you
with an error screen asking if you'd like to erase this iPod and sync
it with the iTunes library. Don't panic. We're not going to erase your
iPod. Take a deep breath and select "Cancel."

Your
iPod's icon should appear in the left iTunes window pane (blue
background). Select the iPod so that the Summary information for your
iPod appears in the main window (see below). Check off the box marked
"Manually manage music and videos." By enabling this feature, your iPod
can be seen by both Mac and Windows machines without prompting you to
erase or overwrite your files.

3. Transfer purchased music to iTunes
While
you've got your iPod connected to your new Mac, it's a good time to
take advantage of iTunes' ability to copy purchased files from your
iPod into iTunes (if only Apple made it as easy to copy the rest of
your music!). We'll show you how to transfer the rest of your music
collection later, but for now, let's just transfer your purchased songs
(if you have any).
Go to the File menu in iTunes and select
"Transfer purchases from iPod". This will trigger iTunes to scan your
iPod for purchased songs and add them to your computer's music library.
iTunes may ask you to reenter the Apple ID (e-mail address) and
password used for your iTunes store account, in order to verify that
the purchased music belongs to you. You may also want to make sure your
new computer is authorized to play your previously purchased music by
going to the iTunes "Store" menu and selecting "Authorize computer."
With any luck, you'll be able to find your purchased music in your Mac
iTunes music library now.

4. Copying the rest of your music
Method 1:
If you happen to have your entire digital music collection stored on
your iPod, one quick way to transfer all your files from an iPod into a
Mac version of iTunes is to download and use a Mac-only application
called Senuti (iTunes spelled backward).
With
your iPod connected to your Mac, and the Senuti application open, you
should be able to see the contents of your iPod in Senuti's iTunes-like
application window. All you need to do now is select all or part of the
songs on your iPod, then hit the copy button in the upper-right corner
of Senuti's application window. After a few minutes of copying, your
iPod's files should now all appear in your Mac's iTunes music library.
Method 2:
If your music collection is larger than what can reasonably fit on your
iPod, then you'll need to copy your PC's iTunes library directly onto
your new computer or onto an external hard drive (you could also
connect your PC and Mac together over an Ethernet connection, but
that's another tutorial). Copying your library onto an external hard
drive is probably the best option, since it gives you an opportunity to
create a backup archive of your music.
To get started, first
you'll want to make sure your PC's iTunes library is ready to
transport. To make sure all your files are accounted for, open up
iTunes on your PC and under the "Advanced" menu select "Consolidate
library." This will make sure that all of the music and video files you
see in iTunes are collected into one main iTunes library folder on your
computer. This step may take seconds or several minutes, depending on
how your music and libraries are organized. You'll also want to go into
the iTunes preferences (found in the edit menu) and make sure that both
the Advanced tab's "Keep iTunes Music folder organized" and "Copy files
to iTunes Music folder…" boxes are checked (see below).

Next,
you'll need to locate your PC's iTunes library folder. It should be
located in the My Music folder, found in the My Documents folder on
your PC's C:/ drive. Once you've found the folder named iTunes, open it
up to find the folder called iTunes Music. The iTunes Music folder is
the one you'll want to copy. It contains all your music organized
neatly into folders.

At
this point, you can either drag the entire iTunes Music folder onto
your external hard drive, or you can create a new folder on your
external hard drive (name it whatever you want) and selectively drag in
just the artists, albums, and songs that you want transferred to your
Mac. Copying large libraries can take a long time, so be patient. If
you have lots of old podcasts clogging your iTunes library, you may
want to delete them from your library before you begin copying.
5. Importing your library onto your Mac
Disconnect
your external hard drive from your PC and connect it to your new Mac.
Now, launch iTunes on your Mac and under the File menu, select "Add to
Library…".

A
window will pop up asking you to locate the files you want to add.
Direct it to the iTunes library folder you copied onto the external
hard drive and click the big blue "Choose" button.

After
a few minutes, your PC's iTunes files should be available in your Mac's
iTunes library. You may have to spend some time relocating album
artwork for some of your old files, but it sure beats burning a spindle
full of CDRs to copy your files between computers.