Searle's first known ship was the 60-ton, 8-gun "Cagway", the largest of four Spanish merchantmen captured by Sir Christopher Myngs as he returned from his raid on Santa Marta and Tolú (Colombia) in 1659. Four years later, Searle captained the "Cagway" as part of Myng's expedition against Santiago de Cuba. This force of 1,300 men and a dozen vessels sailed from Port Royal (Jamaica) on 1 October 1662 and two-and-a-half weeks later disembarked to the east of their intended target. Santiago was overrun the following day and a considerable amount of booty carried back to Jamaica.