This shortcut will look at your calendar and ask you to choose an event with an address. That’s all you have to do! The shortcut will give you a reminder 10 minutes before you have to leave, and set an alarm for the time you actually need to head out.

For rich notification support, use my other shortcut Calendar Event ETA. When the reminder comes up, just let it hang out until it’s time to go. When you leave, force-touch/tap-and-hold the notification to bring up the URL that will launch your directions and start your playlist.