Songfacts®:

• This song about a lost love finds Jackson Browne in love with Jamaica, the daughter of a ship's captain. However, his beloved sweetheart is a restless spirit and she leaves him to travel the seas with her father.
• For Browne, his songs have often hidden sources of personal discovery. He wrote "Jamaica Say You Will" as a fable, inspired by a girl he'd just met who worked in a hillside garden in Zuma Beach, close to the Pacific Ocean.
  
  "In the song, the girl leaves with her father to sail out into the world, but my ships had not found the see as it were," Browne told Uncut magazine. "It became a lament for time spent sheltered in this relationship. I realized I'd been writing about the relationship I'd just left, not this new one I was in. So I learned something about myself and maybe found more closure or solace."
• Browne wrote the song in 1969 and cut a demo that he sent to artist manager David Geffen in early 1970. Geffen signed Browne and began looking for a record deal for the singer-songwriter. He eventually co-founded Asylum Records in 1971 with Elliot Roberts after he couldn't get Jackson Browne a record deal anywhere else.
• Browne recorded "Jamaica Say You Will" for his 1972 self-titled album. Six months earlier, The Byrds laid down a version for their 1971 Byrdmaniax album. Other artists that have recorded covers include:
  
  Nitty Gritty Dirt Band (1972)
  Joe Cocker (1975)
  Ben Harper (2014)
  Los Lobos (2021)