This bittersweet ballad takes the form of a dialogue between two lovers. One of them, the woman, goes away on a long journey across the sea and during the first six verses the pair go back and forth as she warns him she "might be gone a long old time." The last three are all spoken by the man who has been left behind and is slowly witnessing the relationship crumbling before him. When, she writes him a letter saying she may never come back, he requests a gift that would be something to remember his love by - "Spanish boots of Spanish leather."
The melody was inspired by English folk singer Martin Carthy's arrangement of the traditional "Scarborough Fair". Dylan came across Carthy's version during his first trip to England in late 1962 and also used the melody for an earlier composition, "Girl From The North Country."
Americana singer-songwriter Jason Isbell has a line from the tune tattooed on his arm. ("Just carry yourself back to me unspoiled. From across that lonesome ocean.") He explained to Mojo:
"I was at the beginning of the relationship with my wife Amanda, and that song really resonated with me. It has that ambiguity, this line in particular. Dylan knows that he is being desperate and whiny and overbearing and masculine and wrong, I like the beauty of that.
It has a direct kinship to that Leonard Cohen line from Famous Blue Raincoat, 'And thanks, for the trouble you took from her eyes. I thought it was there for good. So I never tried.' Cohen was better at the phrasing, and put more time into the editing, but Dylan had the genius. He could be observing from different places, different perspectives."
Artists that have covered the song include Joan Baez on 1968's Any Day Now, Nanci Griffith on her 1993 covers record, Other Voices, Other Rooms and The Lumineers: for the 2016 Target Exclusive Edition of their Cleopatra album.