Hi Taylor!
Welcome to the Disney Parks Moms Panel. I am a proud "boy mom" myself and I know how important it is to my sons to be "big boys" during our entire vacation! Unfortunately, if you
rent a stroller from the Walt Disney World Resort theme parks or Disney Springs, there is no option for a stroller with sitting and standing options. All strollers are made for children to sit while being pushed. You can check into the
Disney Featured Providers for stroller rental to see if they offer a sit and stand option for you to rent during your Walt Disney World Resort vacation.
When we are enjoying a long theme park day with my boys, I have noticed that even if they are resistant at first, their legs do eventually get tired as we walk quite a few miles through the theme park. I allow them to pick when they would like to walk and when they want to get in the stroller. Often they spend a good portion of the morning choosing to walk during their trip, but as they day goes on, they always take the opportunity to rest their legs when they can. And if I feel like they are resisting taking a break, I will offer a snack like ice cream or popcorn for them to enjoy as we make our way between attractions. That way they can rest their feet, enjoy a snack and you will arrive at your next stop with energy for the awaiting adventure!
Please let us know if you have any other questions as you continue your planning. T-T-F-N, ta ta for now!
~Crystal