You can probably guess that I'm a big proponent of staying on Disney property when traveling to Walt Disney World. We love the convenience and the atmosphere of being immersed in Disney magic for our entire trip. That said, I have stayed off-site when traveling with extra family members, simply because there weren't many affordable suite options on-site to accommodate us all. (Hopefully that will change when the Art of Animation Resort opens!)
Here's a Thursday's Tip for those staying off-site: budget and plan to drive your own car (or a rental car) to the Parks. Even if your hotel has "scheduled transportation" to the Disney Parks, that schedule will undoubtedly be limited. Having the freedom to come and go at will is well worth the $14/day parking fee, in my humble opinion. If you have small children who may require an afternoon nap or--heaven forbid!--a trip to a walk-in clinic (been there/done that), I'd consider my own transportation a necessity.
We stay on Disney property and still actually prefer to take our own transportation to the Parks in most instances. We love the flexibility it affords, and we even pack a small cooler with cold drinks and snacks and often make a late afternoon trek out to the car to refresh our Park stash. And, of course, when you're staying at a WDW Resort, parking at all of the theme parks is free!
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