That same year he took part in the successful Blockade of Western Cuba expedition as captain of the Little John, one of five-ship flotilla under William Lane and financed by Sir Francis Drake among others.
He and fifteen men stole the pinnace later that year and captured several prizes before arriving in Jamaica to join a privateering expedition to Honduras led by Sir Anthony Shirley and Captain William Parker.
On 24 January 1603 Geare and Christopher Newport participated in a joint Anglo-French operation when they directed eight ships during the landing of armed privateers near Santiago, Cuba.
Their advance was halted by the Spanish Governor Fernando Melgarejo de Cordoba, both by a single artillery piece and stampeding a herd of cattle towards the raiders, and they were eventually forced to flee.
[2] Soon after he and Christopher Newport then attacked Puerto Caballos again after they heard that two Spanish galleons were unloading their goods, in a bold move the English and French captured them after a hard fight burning one and taking the other as a prize.