Charles Gregory was born and painted his entire life on the isle of wight, known then, as now, as the yachting capitol of Great Britain and where the schooner yacht AMERICA captured the cup that still bears her name. Gregory was quite well known in his lifetime and considered the premier yacht portraitist of his day, earning numerous commissions from the cowes based royal yacht squadron. His superb marine portraits were sought after by yachtsmen even above those of his well known contemporary Arthur Wellington Fowles.

Gregory worked in both oils and watercolors. It is obvious that he possessed a great knowledge and love of the sea, as it is reflected in the accuracy and merit of his paintings. He exhibited numerous works in London at the Suffolk Street Galleries between 1848 and 1854. As a member of the Royal Society of British Artists he also exhibited with them in 1848-49. Carrying on the tradition, both his son and grandson became noted marine artists as well.