San Bernardino Pass, Switzerland
There are plenty of ways to get between Switzerland and Italy, but the San Bernadino Pass is the only one that matters. The road was originally a mule path, and thanks to the opening of the San Bernadino Road Tunnel in ‘67, now sees a fraction of the traffic it once endured. At its peak, you’ll sit some 6,775 feet above sea level, and you’ll fight through a dizzying myriad of hairpins with a max grade of 9 percent. The road is closed during the winter due to severe snow, but the summer offers crushingly serene views of the Alps and some of the most challenging tarmac in the world.