Even the simplest of routes can present some complex challenges. And forgetting to check the charts can catch you by surprise.
On occasion I have a flight across the pond. No, its not an ocean crossing, although it sometimes feels like it. These flights cross Lake Michigan, and require a bit more planning than flights over land. When you fly around the Great Lakes, its taken for granted that if youre in a single-engine piston aircraft, you have to carefully examine the risks and mitigations. Dont want to cross the lake at all? Fly around it and spend that extra time to stay over land. Not good weather for a crossing? Same deal.