In the recent release of iTunes 11.2 and OS X 10.9.3, Apple brought a measure of joy to those users who missed the ability to sync contacts and calendars over a tethered USB connection. Gone since the introduction of OS X Mavericks, its reintroduction will be welcomed by those who don’t care to sync this kind of data over iCloud.
In case you’ve forgotten how to do it (or you’re new to this business and haven’t experienced it in the past), it works this way:
If you’ve been syncing your contacts and calendars with iCloud and instead want to sync physically with your Mac, you need to first disable these options in iCloud. To do so, go to Settings > iCloud on your device and switch off the Contacts and Calendars options. This tells the device that contacts and events won’t be synced over iCloud. You’ll be asked whether you’d like to keep existing contacts and events on the device or delete them. If you’re sure all the contacts and events on your Mac are up-to-date, feel free to delete the ones on the device. Then connect your iOS device to your Mac via a USB cable.
Now launch iTunes and select your connected device by clicking on its name near the top of the iTunes window. In the resulting pane click on Info and enable the Sync Contacts and Sync Calendars options below. You can choose to sync all your contacts and calendars or specific groups and calendars. Make the most appropriate choices and click the Apply button to sync this data between your Mac and the device.
Note that the Info tab will not appear in the latest version of iTunes unless you’re also running OS X 10.9.3. Also, in my tests with an iPad Air running iOS 7.1.1—where I didn’t already have contact syncing switched on in the iCloud setting—I had to flip iCloud syncing on and then off again before iTunes would recognize that I wanted to sync via iTunes.