While her name remains secret, the "lady of the hotel" still makes her presence known. Anytime of year you can choose from several types of Ghost Tours in St. Augustine, but October is especially appropriate.
In the early part of the 20th century, St. Augustine became a hot bed of smuggling activity, due to the prohibition of the import and sale of alcohol. Much of the illegal rum clandestinely brought into the United States from Cuba entered along the St. Augustine waterfront. The fabled "G-Men" of Eliot Ness fame became frequent visitors to the Old City, and Casablanca Inn, then known as the elegant Matanzas Hotel, became the setting for much bootlegging activity.
The proprietor of the hotel was an enterprising widow of high breeding, who fell into league with the brigands, one of whom she took as her lover. The rumrunners set up shop in her boarding house and sold liquor to the guests and locals who were familiar with the operation. The rumrunners would stay here, right at the St. Augustine waterfront, for a few days at a time, then move along by sea to their next setup.
Apparently it was quite a lucrative business, and the government boys sought to put an end to all this activity. The widow was questioned, but remained silent as she worked out a plan. When the bootleggers were coming through the inlet, the lady would climb to the roof of the building – where you see the pillastered railing today – with lantern in hand. If the government boys were in town, she would wave her lantern back and forth several times. The bootleggers would then know to pass by and travel by the St. Augustine waterfront without stopping. When the contraband liquor could be brought ashore in safety, the infamous lady would reap her rich reward.
Since those days, many a shrimp boat or other watercraft has entered the inlet just after dusk on a moonless night to be greeted by an eerie lantern swinging in the darkness above the Casablanca Inn. Most witness only the light, but some swear they spy a dark figure on the distant rooftop. Perhaps the rumrunner's lady still paces the roof, signalling safe haven to her lover and his cohorts as they cruise by. And who knows...maybe Eliot Ness and his G-Men still roam the St. Augustine waterfront trying to catch them!