The narrator expresses a longing to escape and sail the ocean while reminiscing about a woman named Molly who broke her promise to marry him, causing him heartache. Despite his pain, he still yearns for her.

Meaning of "Handsome Molly" by Doc Watson

"Handsome Molly" tells the story of a man who is heartbroken after the woman he loves, Molly, breaks her promise to marry him. He is filled with regret and sorrow as he reflects on their past together and sees Molly drifting away from him. The lyrics convey the pain of unrequited love and the struggle of coming to terms with betrayal and heartache. The narrator's desire to sail away on a steamboat represents his longing to escape the pain and memories associated with Molly. Ultimately, the song captures the bittersweet emotions of lost love and the difficulty of moving on.