re: Driving to Disney World

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how far is too far to drive before the better option being flying?

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It depends. A lot of parents throw iPads at their kids before they back out of the driveway. I forced my kids to look out the window (pre-teen, no phones) for an hour on any trip, and not use devices.

Traveling is just dead time. 14 hours in a car (with a greater risk of accidents) or a couple of hours on a plane. The mistake that I see everyone make, is "oh hey, this ticket is $7 cheaper per seat," but they don't pay attention that it requires you to fly to Chicago with a 5 hour layover to go from Louisiana to Orlando.

About 5 hours is the limit, unless it involved a f@*% beach trip where I had to pack 600# of crap we didn't need for a five day stay.