Reliance, in the foreground, has hoisted all sail except for her jib- topsail, which crew members are feeding out the bowsprit to be 'hanked' onto the forestay in preparation for hoisting. Crossing just astern of Reliance is Columbia. Her crew are hoisting her jib-topsail (set in 'stops'), a process made easier by heading downwind. Further to windward, on the right hand side of the painting, is the Constitution. Her tug is in the process of retrieving her towrope. An 'old timer', with a 'clipper bow' sails past to windward of Constitution.

On the left hand side of the painting is Rear Commodore Vanderbilt's 233ft. steamer North Star. Alongside her is the big new schooner Ingomar. Further in the background is the town of Newport. The three large America's Cup yachts were each towed out of Newport Harbor and then hoisted sail in the lee of Fort Adam, before heading out to the startline off Brenton Reef lightship. In the America's Cup defense series held off Glen Cove in May, Sandy Hook in June and Newport in July, Reliance won every race against Columbia and Constitution.

Reliance subsequently defeated Shamrock III in the America's Cup held off Sandy Hook in August 1903.
All three defense candidates were designed by Nat. Herreshoff and built at the Herreshoff yard in Bristol, Rhode Island. Columbia won the America's Cup in 1899 and again in 1901. Constitution challenged for the defense in 1901 but was beaten by Columbia.

Reliance was 145ft. length on deck and 89 ft. LWL. She had a steel mast and telescoping wooden topmast. She carried 16,000 square feet of sail and was skippered by the famous Charlie Barr. Ingomar, also designed by Nat. Herreshoff, won the Astor Cup and every race on the NYYC cruise of 1903. She was 127ft. length on deck and 87 ft. LWL. Ingomar marked the beginning of a great line of famous large schooners that was to race under the NYYC burgee for over two decades.