This achievement is simple, but it takes some time. In this guide I´ll show you the fastest way to get it
Route
You have to travel by the red road marked on the map. It´s the fastest way how to get this achievement.
Statistics
You can check your statistics anytime you want, keep on mind that 1 mile is 1,61 km. So to get 1000 miles, you´ll have to get 1609,344 km.
Source: https://gameplay.tips/guides/4752-mafia-2.html