Port Royal Community in Naples, Florida

Port Royal was a sleepy mangrove swamp when it was reimagined in 1938 by John Glen Sample, a retired advertising executive. His vision was to make Port Royal the finest place in the world to live by carving out peninsulas of land for grand estate homes with ample waterways for yachts and other watercraft. Streets bearing names like Rum Row and Galleon Drive underscore its “pirate city” inspiration. Classic cottages and modern, Mediterranean-styled estate homes surround the exclusive, members-only Port Royal Club, with its private beach, exclusive dining, and recreational amenities.