History of Port Royal

Port Royal was founded by John Glenn Sample, a retired Chicago advertising executive who pioneered radio soap operas. Sample first visited Naples in 1938 and began purchasing land that year. Development officially began in 1948, with the first residents moving in by 1952. Sample invested approximately $3.5 million of his personal fortune to transform 2 square miles of mangrove swamps into the exclusive waterfront community we know today.

John Glenn Sample named the community after Port Royal, Jamaica - the notorious 17th-century Caribbean pirate haven that was once called 'the wickedest city on Earth.' The pirate theme extends to street names: Rum Row, Gin Lane, Galleon Drive, Cutlass Lane, Spyglass Lane, and Treasure Lane all pay homage to this colorful maritime heritage. The naming reflects Sample's appreciation for nautical history and adventure.

In the early 1950s, heavy dredging and earth-moving equipment was brought in to transform mosquito-infested mangrove marshlands into the luxurious waterfront community. Workers created man-made peninsulas and picturesque navigable waterways, designing every lot with direct water access to either the Gulf of Mexico or Naples Bay. This massive engineering project would be impossible today due to environmental regulations, making Port Royal's waterfront lots truly irreplaceable.

Sample's stated vision was to 'make Port Royal the finest place in the world to live.' He personally screened every prospective buyer, often touring them in his Silver Cloud Rolls-Royce or his 70-foot yacht 'Privateer IV.' He judged buyers by their manners, conversation, and dress - seeking neighbors who would contribute to an exceptional community culture rather than simply those with the most money.

The Port Royal Club officially opened in 1959 as the community's social centerpiece. Initially, club membership was tied to property ownership, meaning prospective buyers needed Port Royal Club admission before purchasing property. The club features a private beach club, swimming pool, tennis courts, fine and casual dining, and social events. In 2025, the club commenced a $100 million new beachfront clubhouse.

When the community was first introduced to the market, property could have been purchased for less than $10,000. Today, exceptional estates in Port Royal are valued well in excess of $100 million dollars.

Hurricane Donna struck Florida in 1960, causing significant damage to the community established just a year prior. However, the residents and developers rebuilt the community stronger than before. This resilience became a defining characteristic of Port Royal, demonstrating the commitment of its residents to maintaining and improving their exceptional neighborhood.

Port Royal offers direct navigable water access to the Gulf of Mexico via Gordon Pass with no bridges to navigate. This makes it one of Florida's most desirable boating communities. Residents can dock yachts at private docks and reach open water within minutes. Much of the 13 miles of picturesque navigable waterways were created during the original dredging project, and such development would be impossible under today's environmental regulations.

Port Royal's successful dredging and development model inspired similar luxury waterfront communities throughout Naples in the 1960s and 1970s, including Aqualane Shores, Park Shore, and The Moorings. The community established Naples' reputation as a premier destination for luxury living and transformed it from a quiet coastal town into one of America's wealthiest zip codes (34102 has ranked #15 richest in the USA)