A vignette of the 1884 New York Yacht Club's Annual Regatta, the brilliant architect and marine painter A.C. Smith was on hand to observe the schooner CLIO, and likely painted this as a commission for her owner, S.L. Blood, whose house flag is atop the main. The N.Y.Y.C. burgee is on the fore and an American ensign is stiff in the heavy elements. It was a day which was neither "suitin' nor fittin'" for sailing, a popular term of the day. The June 13th race started under drizzle and light winds which quick grew ferocious and challenged most participants to even reach the finish.

CLIO was built in 1873 by C. & R. Poillon of Brooklyn, for Horatio Hathaway of New Bedford. The Poillon yard was responsible for several famous racing yachts, including BANSHEE, SAPPHO, FORTUNA and the indomitable GRAYLING: all designed by Smith. It is subjective, but highly probable, that the yard connection led to this specific art commission. When Blood purchased the schooner in the early 1880's, he had the yacht reworked by Jesse Carll. She measured 75'5" overall x 68' hull length x 18'6" beam x 5' depth with her centerboard drawn up.

Smith sets the day's fast tempo and challenging sea in an inviting panorama off the visible New York headland and the out-of-sight lightship course marker. Undoubtedly, Smith painted some of the yachts he had a personal interest in as well during the event. In all, seven schooners, eight sloops, and five cutters were in the regatta's field. CLIO parted her bobstay and a bowsprit shroud, to finish behind the big schooners MONTAUK and GRAYLING. It would be the racing schooners bellwether event, as the cutters rose to prominence and began to dominate yacht racing for the next 40 years.