The subject, Chepstow Castle, dominates most of the print, sitting across the water from the viewer. It is in a state of ruin: ivy climbs up the towers, and the tops of the rightmost towers are either severely damaged or missing. The sun appears above the castle, gleaming in a wide rift between the clouds.

Light brown cliffs, partially cloaked in dark green plant life, take up most of the left half of the painting. Near the center of the piece two small boats work their way along the river, which curves dramatically from the right border of the painting to the immediate foreground, then back to the horizon, where it meets a mostly-cloudy sky.

Doctor Syntax and the bookseller occupy the center of the piece. Syntax gestures demonstratively at his travel journal while the bookseller looks upward. To the left, the bookseller’s wife is seated in a parlor, grasping a decanter in one hand and a cup in the other, both of which are full of wine.

Dr. Syntax sits on his horse at the center of the engraving, holding an open sketchbook and pen; an open umbrella appears to be tucked under his arm. A local fisherman and his dog stand behind him; before Syntax, on the water, a man rows three tourists in a boat, two of them women.