SyncMate will sync Outlook 2011 calendar and contacts on a Mac running OS X 10.6.6 or higher (Snow Leopard) with an Android device. Sync takes place directly through USB, Wi-Fi, or Bluetooth connections or indirectly by syncing with Google's services.
I will start by explaining how the data will be synced. First, Outlook calendar and contacts will be synced with the Mac's iCal Calendar and Address Book. Then, SyncMate will sync the iCal and Address Book with the Android. The sync also takes place the other direction, so the Android Calendar and Contacts will be synced with iCal and Address Book on the Mac. They will then be synced with the Outlook 2011 calendar and contacts.
Here are the steps you must take for this to happen. First, you must be sure the Outlook 2011 Service Pack 1 is installed, which will enable the Mac's built in Syncing Service to work with Outlook 2011. This will automatically sync Outlook's calendar and contacts with iCal and Address Book. See here for the Microsoft Knowledge Base article for instructions and download links for Outlook 2011 Service Pack 1: http://support.microsoft.com/kb/2452489. You must follow the procedures in step 2 of the afore mentioned KB article to enable the syncing.
Next, the SyncMate software must be installed on the Mac. Afterwards, an app must be installed on the Android device to facilitate the sync. The app will be installed automatically if you choose the USB sync option - in this case SyncMate will install it directly. If you wish to sync using Wi-Fi or Bluetooth, SyncMate will give you a QR code that you can scan using your Android and you will be taken to the Android Market to download and install it. You can also choose the USB sync option to have it installed automatically and then switch to the Wi-Fi or Bluetooth option. Alternatively, you may search for "SyncMate" on the Android Market and install the SyncMate for Android app. It may be important to note that SyncMate likes to call this app a "driver" or "module".
If you wish to sync wirelessly with the Google sync option, SyncMate will first sync iCal and Address Book with Google Calendar and Contacts. You may then set your Android to sync your Android Calendar and Contacts using your Google account to complete the sync.
SyncMate's site gives general information about their product and they kindly replied when I asked them for more information to complete my charts. To find more detailed information, you need to visit the documentation page (link below). There is email tech support available to answer any questions you may have.
While I have not tested this software, I'm glad to see there is a free Mac solution for syncing Outlook Calendar and Contacts. After looking over the documentation, I have found one good reason for purchasing the Expert version: The sync on the free version of SyncMate takes place manually, but the Expert version will autosync. The Expert version does offer many features unrelated to Outlook/Android sync and you will be only be paying $39.95 for it. I personally don't have time to waste on manual syncs, so the extra $40 for the Expert version seems well worth the price in time savings.
Finally, be aware that SyncMate will not sync Outlook notes and tasks to your Android. SyncMate currently only syncs notes and tasks to devices that natively support them. Since Androids do not have a native Note or Task app, the sync is not supported for them.