Sync iCal and Outlook calendars?

MobileMe will keep your iCal, your Outlook and any iOS devices in sync:

http://www.apple.com/mobileme/

Syncs a lot more than just calendars too...

Free? How much do you value your calendar data?

Syncing is a complicated thing to do properly, reliably and without conflicts or data loss and costs considerable amounts of money to develop. 'Free' also generally means no support if anything goes wrong.

You can try Google Sync though, if you and your work are happy to have all your data stored with them, with no support.

Try Google Sync. It may suit your needs. I can't vouch for its reliability though.

I'm not looking for a service to upload/download

Huh? That's what syncing is!!

How do you expect your calendars to transfer between your Mac, PC and iPod without some kind of uploading/downloading/syncing between them?

There has to be a 'central repository' that keeps track of the changes on each device otherwise you'll end up with lost data, duplicates and all kinds of problems.

The ability to transfer calendar data is built-in to the iPod and iCal and Outlook, but there needs to be something else that talks to all three to manage the safe and reliable transfer of data.

iTunes also acts as the go-between from iCal and iPod or Outlook and iPod, but as the iPod is designed only to sync with one computer at a time, I'm not sure how well, if at all, it will handle syncing from multiple computers and what would happen with duplicates etc.

Back up your calendar data and try it if you want.

I know what syncing is. I develop iSync Plugins for "proper" syncing between Macs and mobile phones.

I develop java apps, I keep the working projects on a flashcard that I sync to my Mac and to the work PC. The flashcard is the "central repository" if you will.

Ok... so in that case, what is keeping track of changes to the files on the flashcard? When you plug it into the Mac after using it on the PC, what decides which files are newer and which files to move from the flashcard to the Mac, and which files to move from the Mac to the flashcard? What decides what to do when there is newer data on both?

I suspect you are not actually syncing, but simply manually copying the data each time using the flashcard as the transport medium.

Have you tried configuring iTunes on both your home Mac and work PC to sync calendars to your iPod touch? If so, does it work or is data overwritten?

iTunes on Mac & PC are identical. But the thing is... iOS devices are designed to be synced to only one computer.

So, for instance, iTunes on the Mac doesn't expect changes to have been made to the data on the iPod since it was last synced. I'm not sure how iTunes would handle it if changes are made on the PC in-between syncs with the Mac.

Maybe if your calendars on the Mac had different names to the ones on the PC you'd be ok, but if you were syncing the same calendars, you may run into trouble.

You'd have to try it - but backup your calendars first on both Mac & PC!

EDIT: Here you go, I just found an Apple Support article on the subject:

http://support.apple.com/kb/TS1474

Data loss is likely...