Shepard was assigned to Fighter Squadron 42 (VF-42), flying the Vought F4U Corsair. The squadron was nominally based on the aircraft carrier , but the ship was being overhauled at the time Shepard arrived, and in the meantime the squadron was based at Naval Air Station Norfolk in Virginia. He departed on his first cruise, of the Caribbean, on "Franklin D. Roosevelt" with VF-42 in 1948. Most of the aviators were, like Shepard, on their first assignment. Those who were not were given the opportunity to qualify for night landings on a carrier, a dangerous maneuver, especially in a Corsair, which had to bank sharply on approach. Shepard managed to persuade his squadron commander to allow him to qualify as well. After briefly returning to Norfolk, the carrier set out on a nine-month tour of the Mediterranean Sea. He earned a reputation for carousing and chasing women. He also instituted a ritual of, whenever he could, calling Louise at 17:00 (her time) each day.