Jones spent nearly eight years in Italy, from 1776 to 1783, chiefly in Rome and Naples. He passed his time, he wrote, 'very Agreeably rambling about and Making a Number of Views and Sketches of the Different scenes in this most picturesque Country'. Sometimes his friends among the English artists in Italy, including Francis Towne and William Pars, accompanied him. The road depicted here, overhung with umbrella pines and walnut trees, was a favourite haunt - a 'romantick Dingle' Jones called it. It was while lodging in Naples that Jones made his now famous oil sketches of roof top views.