Sailer started skiing when he was just a little boy. At the age of 2 he was given his first pair of skis. His father Anton, sister Rosi and brother Rudi were also competitive skiers. At the age of 10 Sailer took part in his first race and even then posted success in schools competitions. In 1947 Toni Sailer joined Kitzbühel Ski Club. Sailer was also a successful ski-jumper, however a short while later he turned his attention to Alpine competitions. Sailer went to the technical college in Schwaz, and worked as a glazier and a plumber.