Definitely do-able! But I guess it depends on what type of things you do regularly. Our gang (3 girls ages 13, 11 and 6) is used to rolling along and doing things often. My dh joins us for vacations, but we live in NYC so even rides to school (3-4 subways a day at times) is like its own "Adventureland" and we've been doing that since they were itty bitty things so they know the 'rules of the road', so to speak. We flow very well together and when we are at places like WDW it is just instinct for them to walk a certain way, hold hands and walk behind one another, and generally keep an eye out for one another. Its all in the way you get them used to functioning as a team, kwim. On our last few trips my dh took the girls to the parks by himself while my sister, mother and I did a few spa treatments and lounged. At first I was a total wreck at the thought he might lose one of them, but again, they are so used to traveling together on a daily basis that it was a breeze! I was quite impressed with dh's ability to function into the wee hours with them and he was awesome!! I guess I didn't give him the credit until I realized he could, so if he could do it, then you can too! Practice at home with them, get them used to hanging onto the stroller - one at either side - while you are walking and if they need to let go of the stroller then they should hold onto each other and walk in front of you, never behind, etc. Just little things that will help put your mind at ease and allow them to flow better. Our training as NY'ers helps us tremendously! Nothing like pushing, pulling, shoving your way through the subways with a stroller and 2 kiddos to teach you how to function on vacation! Vacation Boot Camp - NYC Style! LOL