Big Yachts Racing off Nantucket, Early Twentieth Century, Painting II

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. The later built racing yachts were designed primarily for speed and efficiency and 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. However 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.

The first Working to Windward painting by James A Flood

Classic early 20th century sailing yachts