History of Five Flags Inn !! Construction on the Five Flags Inn began in 1963 by a group of doctors. It was being built by Howell Brothers Construction out of Philadelphia, Mississippi. Unfortunately, the money played out before it was finished. It sat abandoned for about two years when the Island Authority wanted it finished or torn down. Ray and Boots Howell approached several men from the Philadelphia and Louisville, Mississippi Area to put up the money to complete the motel. Among these men were Buck and Bobby Clark and Graham Underwood. Woodie Adams and Howard Woodruff came in later. The motel was completed and opened in June of 1965. Buck and Bobby Clark gradually bought everyone else out. The Five Flags Inn was the only thing on Ft. Pickens Road with the exception of one other small motel where the Holiday Inn is today. The pool was originally located on the Dunes end of the motel. It was taken by Hurricane Frederick. The motel struggled for a few years and when the large patio was poured, business began to pick up and has done well ever since. In December of 1992, Bobby sold his shares to Buck's son, Baker Clark and Buck sold his shares to his son-in-law, Mal Williams. The motel is named after Pensacola, the City of Five Flags.