We have twins, and at the time of our first family trip to Disney World they were about to turn four. So we had to think about whether or not to use a stroller while there. The answer to this question, with regards to Disney World, is really based on a number of factors. But for us, it came down to the fact that our nearly four year olds did not like being in a stroller anymore.
We had an amazing double stroller, the Mountain Buggy Urban, and we put it to great use until they were about three. We also had a couple of umbrella strollers for convenience sake. However, our kids liked (and still do) to walk, including a mile long hike in Ontario’s Algonquin Park the summer prior to our trip. We knew they wouldn’t get in the umbrella strollers and we weren’t planning on schlepping the Mountain Buggy on the plane. We didn’t want to risk damage to it, especially when they probably wouldn't want to use it.
We also knew that the shuttle bus came right to the front door of our hotel and it is hard to get strollers on these buses. In some very large Disney resorts, they recommend a stroller just to get to and from the bus stop. We decided that we would take our chances on day one and rent a double stroller from WDW if we needed it. We didn’t. The kids did just fine! Double strollers rent for about $31 US a day (slightly less if you buy multiple days) and they all look the same. Also, some areas can’t be accessed with them and Disney cast members move them all the time. You have to mark your stroller with something easily identifiable such as a handkerchief or risk losing it. We also could have rented a stroller from one of several Orlando companies that deliver and pick them up to and from your hotel or resort.
I am not suggesting that for some a double stroller at Walt Disney World isn't useful or even essential, but for us it worked out better to have not brought or rented one.
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