Hi Jamie: I like that you are thinking ahead. I have two boys, ages 8 and 7, who have been traveling to Walt Disney World since they were infants. When they were almost three year olds, a quality stroller was an essential item for our trip since there is so much walking at Walt Disney World. Plus, a quality stroller provided a great napping spot for them.
You'll definitely want a light and easy to maneuver stroller, so from your two options, I would recommend your umbrella stroller, particularly if it also easily folds up. Parks can get crowded at times, and having a stroller that can easily navigate through and around the crowds of people and other strollers is very helpful. You'll also need to fold up your stroller if you plan to use Disney transportation to get around property to the parks and your resort, and it's likely the umbrella stroller is easier to fold up and carry aboard buses, boats, and monorails. Enjoy your vacation.
Visit Walt Disney World Resort to explore the magic.
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