This is doable, but it is a multi-step process even though it doesn't seem as though it should be. A little over a year ago I switched to a Macbook Pro connected to an Exchange Server and used a Blackberry. The Exchange Server kept everything nice with the Blackberry and Entourage on my Mac. A few months later I left that company and was not connected to the Exchange Server and decided to use iCal and Mail in lieu of Entourage. The problem with Entourage is it is a completely different code base from Outlook and does not really provide the same functionality. Unfortunate, because I love my Mac, but I do miss Outlook. Needless to say through all of my explorations, I do believe there's a way to sync Outlook on one machine with Entourage on another, use Google Sync and another free program call Calgoo Connect.

First, set up a Google calendar that will act as the catch-all for your events. Then go to Google's support page for instructions on setting up Google Sync with your Outlook Calendar. Instructions can be found here:

http://www.google.com/support/calendar/bin/answer.py?hl=en&answer=89955

So now you should have Outlook syncing with Google Calendar. The next step is to get Google Calendar syncing with Entourage. That's a little trickier. You would think not, Outlook and Entourage are both MS products with the same reasons for existing, but they don't work the same way at all at the code level. Thanks to Ben Rapin for discovering a way to sync Entourage with Google Calendar via Calgoo Connect (and iCal), you can read his instructions for that here:

http://www.benrapin.com/blog/2009/05/06/my-quest-to-sync-google-calendar-with-microsoft/comment-page-1/

Or go straight to the source and download Calgoo Connect here if you're feeling frisky and want to figure it out yourself:

http://www.calgoo.com/connect/index.do;jsessionid=D66459998F6DDE0C45F5CEBBE0899CA8

Now Calgoo should be syncing Entourage with the same Google Calendar you already have syncing with Outlook. If your using a Blackberry or iPhone that is set to sync with this same Google Calendar it will all be in the same chain of synchronization as well, an added bonus and exactly why I was on the search for this type of syncing to begin with. Funny I have to use Gcal to sync my MBP with my iPhone....Just as funny as needing Gcal to sync two MS products like Outlook and Entourage.

Anyway, I hope this accomplishes what you're attempting to do. I understand the need for multi-platform sync and someone needs to develop a seamless solution to this issue. It seems Google is almost there.
Source(s):
http://www.google.com/support/calendar/bin/answer.py?hl=en&answer=89955

http://www.benrapin.com/blog/2009/05/06/my-quest-to-sync-google-calendar-wi...

http://www.calgoo.com/connect/index.do;jsessionid=D66459998F6DDE0C45F5CEBBE...

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