I use Outlook for calendar along with my BlackBerry - they make a reasonable combo. If all you are looking for is portable calendar I've found the PocketPC's calendar implementation superior to the BlackBerry (BlackBerry kills in e-mail however).
Exchange server would be a nice touch, but I've been able to survive fine without it. Downside is that calendar has to be synced by physically plugging the device into the desktop where as the Exchange server integration is nothing short of magic.
If you do use Outlook I highly recommend at the very least 2003 since the work week view and general enhancements are what makes Outlook a good calendar program for personal organization imo. I love being able to see my entire week on one screen with the appropriate blocks of time booked off with my appointments.
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