Several sprit-rigged Dutch fishing boats are shown in a strong wind from the left. The boat on the left is in port-broadside view, beating to windward, with several crew in the stern and three others towards the centre. The port leeboard is visible and the sails are at full stretch. A similar boat can be seen in the distance on the right, reaching across the wind on the starboard tack, and other shipping is visible towards the horizon. In the distance the coastline of Holland can be seen both to the right and left. A barrel floats in the water in the foreground.

Born in Rotterdam, Simon de Vlieger was one of the important early painters in the emerging discipline of marine art. He was a member of the Delft Guild of Painters from 1634 and by 1638 was in Amsterdam. He settled in nearby Weesp and remained there for the rest of his life. De Vlieger decisively influenced the direction of Dutch marine art during the 1630s and 1640s. Significantly, as the pupil of Jan Porcellis and the master of Willem van de Velde the Younger, he provided a bridge between the second generation of Dutch marine painters and the third. He demonstrated his versatility and technical accomplishment by painting a wide variety of marine subjects and was also a sophisticated early exponent of the Dutch realist tradition. He moved away from a monochrome palette towards a silvery tonality and demonstrated a closely observed knowledge of shipping. He also painted figural representations for churches, genre scenes and landscapes, and was also an etcher. The painting is inscribed and dated on the foreground barrel 'S.Vl �.44'.