Charles Robert Cockerell was fortunate in being born, in 1788, into a self-made but higher professional family, in a London which was on the brink of its nineteenth century power and wealth. He was one of eleven children in what was a close-knit and loving family. His father, Samuel Pepys Cockerell, was a man of strong will, a successful surveyor, architect and property speculator, and very proud of his descent from the diarist's family. His uncle, Sir Charles Cockerell, had made a large fortune in the East India Company, and Cockerell was related to John Belli, Warren Hastings’ private secretary, and to William Howley, a future Archbishop of Canterbury. Samuel was well able to give his son a gentleman's education at Westminster School, where he arrived in 1802 to acquire a sound grounding in Ancient Greek and Latin, and, no doubt, an ability to take care of himself. Here, each year, he will have seen the Latin Play with its backdrop of Athens devised in 1758 by James ‘Athenian’ Stuart himself, who was to be Cockerell's inspiration and model.

Cockerell left Westminster when he was sixteen, and began architectural training in his father's office, from where, in 1806, he was sent on a tour of the West Country and Wales, which served as a kind of small pilot study for the substantial tour he was to make. But first, in 1809, he was sent to work in the office of Robert Smirke, a friend of his father's, who had just received the commission for the Royal Opera House, Covent Garden. Cockerell worked on drawings for Covent Garden, the large Doric Portico of which was crucial to the development in Britain of the ‘Greek Revival’. Samuel Cockerell, always a man to smell the wind, thought that direct experience of ancient Greek architecture would equip his son to be a leader in what would clearly be the new fashionable style, and in 1810 determined that he would embark on a lengthy foreign tour, originally fixed at three years.

Greece itself was always intended to be the principal goal, although Samuel hoped that Cockerell would be able to experience Italy also, in spite of the fact that most of the continent, including Italy, was controlled by Napoleon and closed to Englishmen.