The Naples we know is full of beautiful homes, golf courses, upscale shops and restaurants, and cultural attractions. But the affluence of today, is perhaps countered by the city’s somewhat less reputable past. While these days the city has nightclubs, eateries, and even neighborhood bars, there was a time when residents were expected “not” to indulge in alcohol. Several historians point to the Roaring ‘20s and Prohibition as a time when the City of Naples was hardly “dry”. Years before towering hotels and high-rises went up in Naples, the city was home to bootleggers, moonshiners, and even rumrunners. It was a time in the city’s history when residents drank secretly at dinner and cocktail parties. As some local historians tell it, getting your hands on alcohol wasn’t very difficult in Naples, even when it wasn’t necessarily legal. Rumrunners and bootleggers were able to utilize hidden inlets and islands, as well as miles of deserted beaches.  From time to time, there were stories about crates that washed up around the Pier, and shipments that were quietly intercepted and carted off by locals. There were all kinds of stories and legends of bootleggers and rumrunners who managed to outsmart local authorities. Some of those stories involved crates of whiskey, rum, and gin stored in local attics. Some homes had their own creative ways of alluding the law too, such as the city’s oldest home, Palm Cottage. It has a hollowed-out table, which was reportedly used for stashing bottles. There were reports of unsuspecting fishermen who reeled in sacks of liquor that were likely thrown into the water by actual bootleggers who were trying to avoid detection. There were also moonshiners who hid out in the Everglades. It’s likely no surprise that there’s now a housing development in nearby Fort Myers called Whiskey Creek. Back in Naples, it’s said the upscale Port Royal community takes its name from a former pirate haven in Jamaica.