K. D-
We are right there with you. Our DS is 3, and while not topping the charts, stands at 40"s tall. We live in NYC, and haven't used a stroller for over a year. We hold hands when walking, take the subway, go into the city, visit museums, zoos etc without a stroller on our home turf.
We'll be travelling to England this spring, and are considering a stroller for our trip. Having DS safe and contained while we navigate the airport, or having a stroller on hand to preserve his energy (walk through pall mall, but then too tired for buckingham palace, or vice versa) feels right to us.
We'll be taking the city mini. Its a bit bit, its a bit unweildy, but it is sturdy, has three large wheels, and will do the trick. It's got a gesture of a basket, not really big enough to hold much, but an ample shade and folds down really easily. If we didn't already have it, I don't think we'd opt to take this. There are better options for this purpose.
Since she is five, would you consider getting a bike or a scooter? We did well with a radio flyer with a push handle for a while. DS was happy to use it, we had an element of control over both speed and destination, and he could coast on it, if he chose to. (doesn't help you with napping though).
Best,
F. B.