Tsao's father began teaching him Mandarin at the age of five using the didactic Three-Character Classic. Tsao entered Shilin Public School (today's Shilin Elementary School) the following year. When he was in the third grade, his father took a job with the Bank of Taiwan and the family relocated to Taipei's Dadaocheng area.
5 歲時曹永和由父親親授漢文，習《三字經》，翌年入士林公學校（現士林國小），3 年級時父親轉任台灣銀行經理，舉家遷居台北大稻埕。