Then he set sail with Sir Francis Drake and Sir John Hopkins, as captain of the "Salomon Bonaventure" in their abortive expedition to capture Panama city. He completed his version of the psalms on 24 January 1595 (now 1596) whilst anchored at the uninhabited island of Scutum (today called Isla Escudo de Veraguas), off the coast of Panama. He called his psalms "Psalmae y Brenhinol Brophwyd Dafydh". Middleton returned from Panama in 1596 and died shortly after his return at Falmouth in Cornwall.