This was originally posted on a previous version of my site, back in December 2009.
Since getting my iPhone, and starting to utilize the functions a bit more, I found myself wanting to have separate personal and work calendars in Outlook, and for these to be synced properly to the iPhone. Anyone who has looked at the Info tab in their iPhone’s sync settings can see that iTunes has provisioned for multiple calendars (you have the choice of All Calendars and Selected Calendars), but it is not quite clear on how to get iTunes to pick up all your Outlook calendars.
iTunes only reads the default data file, typically Outlook.pst in your Local Application Data folder, to read and write your contacts, calendars and notes, and usually any extra calendars you create in Outlook get their own .pst file. The trick is moving the extra calendars in the Folder view to your default calendar so they becomes “subcalendars”.
You may need to restart iTunes and/or Outlook to get iTunes correctly reading your calendar groups, but you should now see multiple calendar groups listed in iTunes. This also works with contacts.
What I’m now trying to find is a way to have multiple groups sync from Outlook to Google Calendar, now that you can add your Gmail, Google Calendar and Google Contacts to the iPhone as an Exchange account (really they’re only implementing the ActiveSync part of a normal Exchange server, which makes Outlook->Google a bit harder).
Update (3 July 2011): As far as Outlook<->Google syncing goes, Google’s Calendar Sync tool only does the default calendar. I’ve started writing my own add-on for Outlook that so far is going pretty well, even if it is just doing calendars. It may be a little ways off, but I will post it on this site once I finish it.