The cross-country phase is an exciting stage of flight training that pushes back the boundaries of your aviation universe, builds your endurance, and offers a taste of your aircraft’s capabilities as a traveling machine. Flights to varied destinations expose you to quiet strips or buzzing terminals—and may take you through numerous airspace classes. (For operations in Class B airspace and at airports located within Class B airspace, make sure you meet the requirements and possess required endorsements.)
Keep in mind that using pilotage to fly destinations in urban environments can present different challenges than selecting and locating checkpoints did on other cross-countries. And because the communications component of flights into busy airspace takes on critical importance now, you may have to locate the proper checkpoint and then report your position as precisely as possible.
That will take great skill and care, with all those buildings, railroads, highways, and interchanges down there. Suppose you are approaching your destination from the west and have been instructed to report at 10 miles west when over a specific highway. Can you tell the many roads apart as they weave their way through the urban sprawl?
One pilot who misinterpreted an assigned reporting point—an error that resulted in an airspace incursion—concluded that "being relatively new to the area and unfamiliar with the terrain and landmarks" contributed to the error, the pilot said in a report to the Aviation Safety Reporting System (ASRS).
What about weather conditions? A pilot noted the contrasting presentations of a chart and the view from the cockpit in this August 2003 Flight Training magazine article:
"The haze rendered many details shown on the sectional chart difficult to pick up until we were relatively close. And, much of the detail that was visible through the haze was not depicted on the sectional chart. For example, there were many more roads than were shown on the chart."
Studying aerial images and photos beforehand revealed “the true shape of the town, individual streets, identifiable buildings, parks, and baseball fields.”
Chapter 15 of the Pilot’s Handbook of Aeronautical Knowledge provides general guidance for selecting checkpoints, and introduces the technique called bracketing to keep you from straying from the desired track.
"If possible, select features that make useful boundaries or brackets on each side of the course, such as highways, rivers, railroads, and mountains," it says.