Allusions and texts of the song's silings begin to appear in the 1890s.

From "The Pilot" (Boston, Mass.) (Aug. 30, 1892):

         "As Jack was a walking down Ratcliffe Highway,
         A fair pretty maiden he chanced to espy;
         But when he did see her most beautiful face,
         Why, he hoisted his topsails and to her gave chase.
                  To me ‘ow di – ‘ow derry way.

"After relating the sailor’s adventures with this damsel, the song goes on to point its moral:

       "Now all you young sailors take warning by me,
       Avoid the highway when you go on a spree;
       And all you young maidens take warning I pray,
       Don’t rattle your rigging down Ratcliffe Highway."

The refrain suggests this example was sung to a "derry, derry down" tune."

To "rattle the rigging" sounds injurious here, but it literally means to affix or make taut the ratlines on standing rigging, as on a rope ladder.

"Cruising Round Yarmouth" is more widely known as "Ratcliffe Highway."