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Armstrong worked as a musician aboard Streckfus steamers, including the Sidney, between 1918 and 1921, under bandleader Fate Marable — a formative stretch in his early career, playing for varied audiences along the Mississippi.

This is a complete harbor guide booklet produced by the Streckfus Steamboat Line of St. Louis for passengers aboard the Steamer Sidney, used for sightseeing tours of the New Orleans inland harbor. The outer cover, printed in deep red and gold on yellow stock, centers on an image of a ship's steering wheel surrounded by industrial waterfront illustrations, reading "Sightseeing Tours of New Orleans Wonderful Inland Harbor" on the left panel and "Steamer Sidney," "Daily from Canal St. Dock, 2:30 P.M., Phone Main 4504" on the right; flags on the illustrated vessel read "Streckfus Steamers."

The reverse of the cover, printed in dark green on the same yellow stock, reads "Sight-Seeing, Excursion Steamer 'Sidney,' Safety and Speed, Comfort, New Orleans Harbor Trips, Leaves 2:30 p.m.–Daily–Returns 4:45 p.m., Phone Main 4504," and notes the vessel's "Mirage Palace" promenade dancing floor, along with "Moonlight Dancing Trips: Leave 8:30 P.M., Best Dance Orchestra in the South." The interior holds roughly thirty numbered white pages interleaved with full-page advertisements.