At the turn of the nineteenth century, the British love of sailing caught on in America, where the elegant racing yachts began to show up in the northeastern waters. Built for beauty and pleasure as well as competition, the yachts were magnificent in their size and elegance. Later, as the America's Cup came onto the scene, the passion for winning overwhelmed the sport, and those racing yachts that were built later were designed primarily for speed and efficiency, strictly with a competitive edge in mind.
In this painting two of the earlier sailing yachts are depicted engaging in sport well off the coast of Nantucket. Both skippers are cutting it close, sailing very near to the wind, but their judgment comes from years of experience. In just moments, the yacht to the left of the viewer will pass within feet to leeward of the taffrail of the yacht off her starboard bow; both will clear.
Fourth in the Jim Flood Series "Great Age of the 'Big Boats' this painting, Working to Windward Revisited, a new original, is a remake of the first Working to Windward. Here James has slightly changed the atmospherics, the angle of the sailing yachts, and brought forward the background lighthouse.