LifeinAsia - 7:06 pm on Mar 14, 2011 (gmt 0)
Quit while the boss is actually on vacation - and make sure they know about it. Monday's always a good day for that. Let them either decide to have a crappy vacation, or come home to look after business.
Actually, I once turned in my 2-week notice as I was leaving for a week's vacation where I would be unavailable by phone (and this was before e-mail, so didn't have to worry about that pesky channel either). One of the most relaxing vacations I'd ever had! :)
Time the notification for right when they're starting to settle into the vacation- maybe a few hours after arrival at the destination? Or, send a text message just before the plane's departure. (If the boss is always online, bonus points for sending it to his phone in a text message 1 minute before he has to turn off the phone for take-off.)
Seriously though, I know these things may be posted in jest, but as fun as it may sound, always avoid anything malicious or criminal (but annoying is fine). If the boss is that big of a jerk, expect retaliation (whether from the police or a lawyer). If you continue to work in the same industry, assume that anything you do will eventually find its way to the ears of any and all potential employers (now and future).