The painting depicts the Rainbow, in the foreground, racing against the Endeavour I, in the background, in race 1 of the America's Cup, Monday September 17, 1934. There was a fresh south westerly breeze of 15 knots, gusting more than 20knots and this created quite a swell on the race course, set offshore from Newport, Rhode Island, USA. The race was a 15 mile slog to windward, followed by a 15 mile run to the finish.
Both yachts have just rounded the windward mark, Rainbow leading by 18 seconds. Both yachts hoisted their spinnakers in stops, Rainbow has broken her's out and lowered her jib. She is surfing on the swells, approaching from her starboard quarter, which cause her to roll to leeward. Endeavour I can be seen breaking out the stops in her spinnaker and her crew are preparing to drop her jib. However Rainbow hoisted her small parachute spinnaker, unlike Endeavour I who hoisted her large parachute spinnaker and passed Rainbow on the run to the finish.
Harold Vanderbilt was the skipper and also managed Rainbow. He can be seen at Rainbow's wheel. Alongside him is the navigator, Professor Bliss, of Brown University and backup skipper John Parkinson( usually sailing Rainbow downwind). Starling Burgess, Rainbow's designer, is seen in the dark jacket and yachting cap, further to windward of the group around the wheel. Sherman Hoyt was also on board, in charge of the spinnaker and jibs. He can be seen in a dark jacket just to windward of the mast. The weather is hazy with sunlight reflecting off the water around the racing yachts. A large spectator fleet is visible in the background with J. P. Morgan's large steam yacht Corsair IV the closest to the yachts.

Endeavour I won both the first and second races but Rainbow won the next four thus retaining the America's Cup. Endeavour I was skippered and managed by T.O.M Sopwith. Both yachts were built to the J Class measurement. Rainbow was 126.7ft LOA and Endeavour I was 129.8ft LOA. Endeavour I was saved from lying in a mud berth in the UK and was rebuilt by Elizabeth Myers and now sails worldwide( different owners) to take part in J Class regattas.
The 1934 America's Cup was the first time that biplanes and high wing mono planes took photos of the racing yachts
Dimensions: 750mm x 1000mm
Media: Oil on linen