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A painting of a historic race such as the one above of Reliance and Shamrock III in 1903 America's Cup, can take weeks to prepare.
I like to begin with finding out the details of the race from the location, time of day, weather and wind direction and the sea state on the day. All of this gives me a feel for how the light will be used in the composition: whether it will be better to have the yachts beating into wind or gull-winged with the light coming through the sails. Which would work better with a choppy sea or calm reflective water.
Next I can move onto some quickly drawn work up sketches with boats at different angles and stages of the race to decide which idea has the most impact visually. Once I have a clear idea of the composition, I will begin a detailed sketch of each yacht. There may not be any good photographs or indeed any pictures of older yachts, which is where the original plans from the yacht designer will come in. I can use these to accurately draw the yacht starting with the mast at the correct angle for my composition and working down to the hull. I include the keel in the drawing to see how the hull sits in the water