Here’s a low-effort option: Let the Windows Migration Assistant do the transferring for you.
Now, this app has a reputation for bugginess. But if it works on your system, it’s a nearly effortless automatic tool that copies all your important data from a Windows PC (running Windows XP SP3 or later) to your Mac. (And if it doesn’t work, Manual Network Transfers offers manual techniques that can do the same job.)
On the Mac, you’ll find the Migration Assistant program in your Applications→Utilities folder. Before you open it, make sure your Mac and PC are connected to the same network (Wi-Fi or wired), as described in Chapter 16.
Now open Migration Assistant. Choose the first option: “From another Mac, PC, Time Machine backup, or other disk.” Click Continue. (Enter your password if you’re asked for it.)
When all is said and done, here’s what it accomplishes:
Transfers your email into Mail from Outlook, Outlook Express, Windows Mail, or Windows Live accounts (POP or IMAP). Your messages even show up correctly marked as having been read, replied to, and flagged (except if they originated in Windows Live).
Transfers your address book into Contacts from Outlook and Outlook Express contacts, and from Windows contacts in the Contacts folder on your PC.
Transfers your calendar into Calendar from Outlook’s calendar.
Transfers your iTunes collection into iTunes for the Mac from iTunes on Windows. Everything comes over, including music, photos, videos (but not rentals), ...