As was already mentioned, a double side by side stroller won't be an issue Before making your final decision, you might want to consider a couple of other things: - are they used to sitting next to each other for long periods of time in the double stroller? If not, you will want to get them used to it. - a double stroller does make it possible for one person to push both children. That would be really nice if you are alone at all with the children. - what will you do if one is having a good day, going on attractions, etc. and the other is not doing so well or needs a break? With only one stroller, you would have to decide which child stays in the stroller and which goes without. - if you are going to be using the WDW buses, the double would be more bulky , but possibly easier to hold on the bus than 2 separate strollers. -some people have had good results with devices that attach 2 umbrella strollers together. They seem to work best with children pretty similar in size and weight. There are no wrong answers - just wanted to give you some more things to consider.