https://en.wikipedia.org/wiki/Mathias_Rust
Small plane lands near Red Square by the Kremlin in 1987.
A teenage amateur pilot, he flew from Helsinki, Finland, to Moscow…
The Soviet fighters did not receive permission to shoot him down, and his aeroplane was mistaken for a friendly aircraft several times.
…Rust, aged 18, was an inexperienced pilot, with about 50 hours of flying experience at the time of his flight.