How did Eratosthenese synchronize the measurements? That seems like the biggest challenge: sync'ing two clocks and transporting one to a place 500 miles away without losing time? 2000 years ago?
And assuming Syene is on the same longitude as Alexandria[0], Syene's noon is Alexandria's noon.
Alexandria: 31°11′51″N 29°53′33″E
Syene: 24°05′20″N 32°53′59″E
Tropic of Cancer: 23°26′10.4″ N
[0] It isn't, which contributed to the measurement error, but close enough is good enough.