Refurbished, the destroyer got underway for the Caribbean on 8 January 1917. Steaming via Hampton Roads, Virginia, she reached Culebra Island, near Puerto Rico, on the 14th and conducted war games exercises with the Atlantic Fleet. In the course of those operations, she visited the Dominican Republic as well as Guantanamo Bay and Santiago in Cuba. Later that month, "Wainwright" carried Assistant Secretary of the Navy Franklin D. Roosevelt; Brigadier General George Barnett, the Commandant of the Marine Corps; and the Chairman of the Civil Service Commission from Santiago to Port-au-Prince, Haiti. Following that assignment, "Wainwright" conducted torpedo exercises, patrols, and power trials near Guantanamo Bay until the beginning of March.