When you fly into somewhere like San Diego or New York, you fly right over the city and are basically directly next to skyscrapers. But when you fly into somewhere like Austin or New Orleans, you’re flying over flatlands. How do pilots know clearance for certain areas, does ground control tell them how best to land or does that not matter?
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For aircraft flying under instrument flight rules there are minimum vectoring altitudes that Air Traffic Control is allowed to vector aircraft down to, and instrument approaches all have minimum altitudes and are built specifically to guarantee that as long as a pilot is correctly flying the procedure he will maintain the required separation from any and all obstacles. The same is true for departure procedures. Basically as long as a pilot follows the published instrument procedure, they can be sure they are well clear of any obstacles regardless of where they are.
For visual flight rules, there are charts that have the altitudes for big buildings and towers marked, but really its on the pilot to look outside and make sure they fly high enough or far enough away from any obstructions to stay legal and safe.
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