I have been trying different methods of synchronizing my Calendars for many years, and I have finally settled on a method that works for me and is pretty much maintenance free. That method utilizes Google Calendar as my hub and a combination of Google Calendar Sync and an excellent program called gSyncit ($9.99).
Google Calendar supports multiple calendars and lets you publish/share them to other calendar tools like Outlook. Google Sync will synchronize your Outlook calendar to GMail, but it has limitations, and will only synchronize one calendar. I use Google Calendar Sync to synchronize my work calendar with Google Calendar. I renamed my main Google calendar to “Work”. Using Google Calendar Sync on my work computer, I push my work Outlook calendar to Google Calendar. I have my work Outlook look at my other Google calendars as Internet Calendars.
At home I use Outlook to get my calendar to my iPod and Windows Mobile phone. Pocket Outlook only has one calendar and Activesync will only sync one calendar to Outlook. gSyncit is a way to get around that limitation.
gSyncit will synchronize all your different Google calendars to your Outlook calendar. It does this by using categories. Each Google calendar ends up as a different category. My Work calendar ends up as category Work. There are several options for configuring the sync process and controlling what gets synced where. It is easy to setup, so it is very easy to try out before buying. It worked so well for me I only used it for ten minutes before deciding to pay the $9.99. gSyncit has other features besides the calendar sync, it will also sync your contacts with GMail and that includes photos.
Once I had gSyncit syncing my Google and home Outlook calendars then my Windows Mobile phone and iPod automatically benefited and were now syncing with all my Google Calendars.
It may seem complicated, but it has actually been simple, painless, and problem free since I set it up several months ago. I update my personal and work calendars during the day and when I get home and sync my phone my calendars are all synced. The few hours that I am out of sync I can just go to Google Calendar and get the latest info.
gSyncit – http://daveswebsite.com
Screen shots of some of the gSyncit synchronization options: