James Hakewill was born in 1778, the second son of John Hakewill. He studied architecture and later entered the field as his chief profession, though he was a proficient painter as well. He exhibited some of his designs at the Royal Academy of Art on at least two occasions. He came to Jamaica in 1820 and remained on the island until 1821. He subsequently published in 1825, "A Picturesque Tour of the Island of Jamaica" from his own drawings.
During his almost two years stay in the island, Hakewill did not restrict himself to Kingston and its suburbs but he travelled to many parishes. Drawings of the Estates situated in St. Mary, Portland, St. Thomas in-the-East, Trelawny and St. James are among his best. His reproductions are not duplicated even though, Adolphe Duperly has made daguerreotypes of Montego Bay, the settings are entirely different. His views of Monetgo Bay from Reading Hill is said to be one of his most beautiful. Although these illustrations of Jamaica do not fall in the category of truly great masters, the charm and delicate attention to detail found in their works cannot but impress those with whom they come in contact.