Since you are using Mavericks/iTunes 11, you will have to consider using iCloud for syncing.
iTunes 11 for Mac: Sync contacts, calendars, and other info with iPod, iPhone, or iPad explains this option.
I find iCloud convenient and reliable for Calendar syncing. Since you appear to have the required equipment and software, I recommend that you consider using it.
If security of your data is a concern read:
Setting up iCloud is best described by reading:
I recommend reading this thread:
The problems with iCloud (and the removal by Apple of local synching) have been very throughly discussed. The thread has attracted 263,000 views. Many people are unhappy with Apple's present business practices.