This drawing is among the finest of Jan Bruegel’s maritime drawings, not only in its high level of finish but also in its delicate use of wash. In the 1997 exhibition catalogue it was compared to his painting of Two Dutch Warships, signed and dated 1599 (Private collection; K. Ertz, Jan Brueghel der Ältere (1568-1625) Kritischer Katalog der Gemälde, Lingen, 2008, I, no. 151), which is one of the earliest marine pictures by Bruegel in which there is no biblical or mythological significance but simply a desire to represent a naturalistic landscape. The drawing is also close to the Marine landscape in a storm, executed in 1614, in the Kupferstichkabinett, Berlin, although the spirit and atmosphere of the two works are very different (Essen, Vienna and Antwerp, op. cit., no. 172). The mood is perhaps closer to two other drawings by Bruegel showing vessels in a calm: the Fishing boats on a river with a mill in the Rijksmuseum, Amsterdam, and the Fishing vessels on a river in the Louvre (M. Schapelhouman, Netherlandish Drawings circa 1600, 's-Gravenhage, 1987, no. 9; and F. Lugt, Musée du Louvre: Inventaire Général des Dessins des Ecoles du Nord: Ecole Flamande, Paris, 1949, I, no. 483). However, none of these drawings approaches the technical finesse of the present work, in which the smooth, glassy surface of the water allows Bruegel to suggest sparkling light and subtle shadow through overlapping thin layers of translucent wash.
The drawing is usually dated late in Bruegel's career, to circa 1620. However, the warm light, the tower in the background, and the style of the vessels seem more evocative of Italy than Flanders. Similar boats appear, for example, in a drawing in a German private collection, generally dated circa 1595-96, which shows the Castel dell'Ovo in Naples (Essen, Vienna and Antwerp, op. cit., no. 153) while drawings and paintings of more northern shores tend to depict heavier vessels. Some drawings executed during Bruegel's long stay in Italy from 1589 to 1596 show a comparable use of wash, such as the Hilly landscape with figures near a ravine in the Art Institute of Chicago, which dates from 1595 (Helen Regenstein Fund, 1987.13; From Pontormo to Seurat: Drawings Recently Acquired by The Art Institute of Chicago, exhib. cat., New York, The Frick Collection, 1991, no. 7).