Whittaker was born in Sydney, New South Wales, the son of journalist Bill Whittaker , and attended Newington College (1978-1983).

In 1985 Whittaker commenced as a copy boy with News Limited and became a staff writer on The Weekend Australian in 1993. Seven years later he left the Magazine to travel around Australia and write. He has since rejoined Australian Magazine as a part-time staff writer.

Whittaker and his wife and co-author, Amy Willesee , won the 2002 Asia-Pacific Travel Writing Award for their book on the Kathmandu royals murders.In 2005, Whittaker won the Walkley Award for Magazine Feature Writing for The Weekend Australian article Ordinary Heroes.