Why was Wesley allowed on the bridge? And even worse, why was he allowed to pilot the ship?
Picard was trolling by putting the kid 'at the wheel of the car' so to speak, a 'car' packed with 1000 people, the flagship of the fleet. It was his sense of humor.
The Enterprise-D had the worst helmsmen. Imagine if the Enterprise-D could land like Voyager could. How scuffed and banged up would it be? Paris was actually probably the best helmsman in Star Trek (now, if Harry Kim was at the helm, Voyager would have steered into one disaster after another). Sisko could have let Jake play around because the station was in park.