Avery painted coastal and waterborne scenes with bold simplified forms and luminous atmospheric color fields that closely mirror Bradford's expressive approach to leisure on water. His serene marine compositions share the same contemplative mood and vibrant yet harmonious palette found in Pleasure Boat.

Fischl works in oil on canvas with a similarly expressive and gestural figurative style, frequently depicting scenes of leisure, pleasure, and social life near water with dynamic brushwork. His attention to the psychological and sensory energy of recreational moments aligns closely with Bradford's subject matter and painterly immediacy.

Porter painted boats and coastal New England landscapes in oil with loose expressive brushwork and a serene atmospheric quality that strongly resembles the mood and technique of Pleasure Boat. His contemporary American figurative landscapes share Bradford's blue toned luminosity and confident gestural handling of paint.