Confused by Mavericks’ new “travel time” feature within Calendar and aren’t sure how it’s supposed to work? Hey, I'm here for you. There are quite a few steps involved for how it functions, so let's get started. I promise that it's fairly painless. Mostly painless. OK, there may be a little pain, but I'll hold your hand.
First, let’s make sure your Mac has access to your current location to take full advantage of this. Do that by visiting System Preferences> Security & Privacy, and then pick the Privacy tab. Under Location Services, “Enable Location Services” should be checked, and you should also allow Calendar to use your location if it’s been deselected from the list.
(Note that you’ll have to click the lock in the lower-left and enter your administrator password to make any changes to these settings.)
If you’re über-paranoid, you don’t have to turn this on; if that setting is off, then Calendar will use whatever address you’ve got configured on your personal card in Contacts for calculating travel times.
When you've got things all ready to go, first create an event in Calendar, and then in the “Add Location” field, type in the address or business name where your appointment’ll take place. You can use contacts' names, too.
Here’s one of the big tricks of using this—for now, you must select one of Calendar’s suggestions to accept it as the location. If you don’t do that, travel time won’t work, even if you type in a perfectly valid address. I'm really hoping that Apple fixes this in a future update, as it sure isn't intuitive for most people. And by "most people," I mean me.
Anyhow, you’ll know that you’ve done things correctly because you’ll see a little map of the location appear within the event window.
Afterward, set a time for your appointment—travel time won't work for all-day events. Then click on the “Add Alert, Repeat, or Travel Time” section…
…and when you select the “Travel Time” drop-down, you’ll see both walking and driving times to your appointment’s location.
Pick one of those, and you can take advantage of another new cool feature—under the “Alert” drop-down, one of the choices is now “When I need to leave.”
So you can get notifications right to your Mac (or your other iCloud-enabled devices) telling you when you've gotta go!
I think I should just go ahead and set that particular event to repeat every half-hour or so. It really is for the good of mankind.