Standing out of San Francisco Bay on 11 May 1943, "Whipple" sailed for the Caribbean with a convoy routed through the Panama Canal for Santa Anna Bay, Curaçao, Netherlands West Indies. After the cargo ships loaded a petroleum cargo, the convoy pushed on for Cuba and arrived at Guantanamo Bay on 29 May. From Guantanamo, the destroyer escorted a convoy to Trinidad but returned to the Cuban base on 19 June before heading north to the New York Navy Yard for voyage repairs.