Before trading his drafting board for a full time easel, Archibald Cary Smith was one of America's premier yacht designers. The subject vessels in this work are two cat-rigged craft known as "sandbaggers". The cat-rig features a single mast situated well forward, near the bow, and carries only a large single sail with no standing rigging. "Archie" Smith was an early builder of these "sandbaggers", so named for the movable sandbags they carried for ballast.

Fishermen along the New Jersey coast established a need for a very small vessel of light draft, for sailing in shoal water and for mooring on mudflats. Smith was an avid catboat sailor, and designed his first, the 25 foot COMET, in 1862. The center for building and sailing "sandbaggers" was New York Harbor, particularly Oyster Bay with its miles of mud flats, which were free to all who cared to moor on them.

Shown on what is likely Oyster Bay with Long Island in the background, Smith portrays two cat boats on opposite points of sail. The artist shows much activity in the background with numerous vessels under weigh. The foreground vessel is obviously a yacht, with its dapper four man crew enjoying a lively sail in the comfortable oval cockpit. Like many of Smith's paintings, this is likely a painting of a yacht that he designed. The protruding submerged trees and choppy sea state illustrate the boat is in shoal water, conditions ideal for its shallow draft. Off the yacht's port bow, heading in the opposite direction, is an open boat type, more conducive to fishing and commercial work, being single handed by a lone figure at the helm.