Leaving Faceville, Georgia at the end of December 1899, Moore headed for Punta Rassa, Florida, near the city of Ft. Myers, about 450 miles by road. His destination was the Tarpon House, formerly a military barracks for Fort Dulaney. The Tarpon House provided room and board for wealthy northerners who came to fish for the famed tarpon using a rod and reel. Tarpon is what drew Moore to Punta Rassa and it is evident from his photos that his party was successful. He mostly photographed the people he was with, but also the staff of the Tarpon House where he was staying. Moore would stay a month or so and then head north to Tallahassee where he would purchase a new, larger camera. The new camera used glass plate rather than film negatives and had a size of roughly 6x4 inches, or twice the size of his old camera.

Moore returned to Punta Rassa on March 9, to have lunch with his cousin, Clarence Moore, aboard Clarence's boat "Gopher". While there he took a few photos of an old cattle barn with his new camera, one of which he would enter in the 3rd Camera Club of New York members exhibit. He then returned to Tallahassee. He would return to Punta Rassa for the last time in January 1901.