re: Disney Pros, is it worth it to stay on site?

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Yeah we are getting off the plane hopefully at 11:30 ready to go to the park.

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You're looking at about a 40-minute ride from MCO to your park. Different parts of Orlando. Uber should be able to get you up to where the other taxis go, which is works well for all of the parks except Magic Kingdom where you'll need to either take the boat or monorail to the park gates.