We decided to stay on Disney property for our visit this year. Disney hotels are definitely more expensive than a similar hotel off-property. But, overall, I think it was worth it. There are a number of extra benefits you get that make up for the price:
1) Disney Magical Express is an included transportation option. When you head to Orlando, you put special yellow bag tags on your checked baggage. In Orlando, Disney grabs your bags at the airport, directly from baggage handling, and transports them to your room. Meanwhile, you take a nice bus to the resort. Later in the day, your bags arrive. And I'll be damned if it didn't work just as advertised. It's really nice to not have to schlep bags. The downside is that it can take up to an hour to wait in the needed lines to get on the bus. It took nearly an hour for my wife, from touchdown to the bus leaving the airport. For me, it took about 15 minutes to get on the bus, mainly because the stupid shuttle driver from my business hotel dropped me off at the wrong terminal. (The business hotel is right next to the airport. So I took their shuttle to the airport, then used Disney to get to the resort.) Of course, once on the bus, we waited 15 minutes to get more folks on. In the additional 15 minutes, we added one whole rider.
2) The service works in reverse as well. We were able to get our boarding passes and check our bags at the hotel and the bags just magically showed up in Richmond.
Magical isn't really that far off the mark.
3) Once you're on-property, you can also ride Disney busses from your hotel to the parks. (And between some parks.) This worked really well. The longest I think we ever waited for a bus was 15 minutes. And, if you're heading to the Magic Kingdom, they drop you off near the door, not on the other side of that fake lake. The only downside here is that they pack the busses really full and we occasionally had to stand. Oh, and when waiting at the hotel, we would inevitably see busses for the three parks to which we weren't heading before our own showed up. Still, overall, the bus system worked great.
4) If you're staying on-property, you also get extended hours at the parks. Basically, each day one park either opens early or stays open late just for on-property guests. That's really nice. We managed to pack in a few extra rides each day during those extra hours and their shorter lines.
There are, however, some downsides to staying on property:
1) The rooms are expensive. Not Norway expensive, but not a whole lot less, either.
2) The food is really expensive and pretty much sucks. But, you don't have a choice, because you don't have a car and can't drive anywhere. (Unless you rented a car. But not needing a rental is one of the things that offsets the high Disney room prices.)
But if you're willing to live in Mickey's all-encompassing embrace for the duration, staying on-property works out really well.
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