honestly, and i really don't know the stamina of your family, but i did something quite similar about three years ago and it almost ruined the trip. i can go-go-go, but for the others on the trip, it was too much for them. if you are trying to do rope drop each day and stay until they throw you out it can be really exhausting. there is a wall that you hit after 'running' hard several days in a row. also, it's amazing how many miles you cross when you are sight-seeing through the parks--one time i logged 23 miles!!!!
if you are certain you want to try it, i strongly suggest a stroller for your little one. there's nothing that can stop a day in its tracks more than an exhausted, overstimulated child.
other than that, have fun. it is you who knows your family best, and you can prepare for whatever if you know all the things you will come across.