The original developer of the Port Royal community was a retired advertising executive from Chicago by the name of John Glen Sample, who arrived in Naples in 1938. He found the area to offer all the stress free living he was looking for, and the lifestyle would include fishing, gardening and boating. So he purchased a beachfront lot in order to build his first home in the area. Subsequently for the next twelve (12) years he went on to acquire more small parcels of land for approximately $54,000 and named the area Port Royal, a name that originated from a major city and harbor in Jamaica founded by the English. His intent was to create a community of like minded residents who understood his vision, so he began to market Port Royal in 1948 and sell off the last remaining lots in 1956 for around $11,000 per parcel.
After selling off the Chicago Advertising agency, he invested all the money from the sale ($3.5MM) into Port Royal and his vision became a reality. By the 1960s Port Royal homes began to increase in price jumping threefold. When the Port Royal Club became an amenity filled pastime for the residents of Port Royal in 1959, eligibility was limited to those who would pass the membership committee, which was made up of Glen Sample and his wife, and applicants needed to provide the names of other Port Royal residents via letters of recommendations, a tradition which continued after his death until a lawsuit discontinued this policy in 1973. As the Port Royal residents grew, so did the desire for membership in the Port Royal Club. Therefore, Port Royal lots that were not even on the water would sell off quickly, in order for these residents to gain access to the Port Royal Club. There were no known restaurants in the area, so the Port Royal Club provided residents with dinner and these non-waterfront lots would increase manyfold over the years.
In order to attract more residents to Port Royal prior to his death in 1971, Glen Sample founded the Hole in The Wall Golf Club in 1958 so that a limited number of Port Royal residents could enjoy the traditions of a golf game with no tee times. The Port Royal Community witnessed strong sales growth of Port Royal real estate due to the club. This growth demanded better community services, such as a church and hospital, which was later constructed to become Naples Community Hospital and Trinity-By-The-Cove Episcopalian Church.
Other parcels of land within the Port Royal area that were privately owned were subsequently purchased via private deals. The intended plans for all homes in Port Royal called for homes that ranged approximately 3,000 sq. ft. in size and featured traditional architecture. Today many mega-homes have been constructed and Port Royal homes are known as some of the finest in the area.