Because of its sheltered, deepwater port, Fernandina was much more important than Jacksonville during the 18th and 19th centuries. It was the starting point for David Yulee’s railroad across the state to Cedar Key, and it was on the border between Spanish Florida and English Georgia, making it a haven for smugglers — a tradition that continued right through the Spanish-American War and on through Prohibition. Author Stephen Crane (Red Badge of Courage) came to Fernandina in 1897, fell in love with brothel owner Cora Taylor and shipped out on The Commodore, which was smuggling guns to rebels in Cuba. The Commodore sank near Daytona Beach and Crane turned the incident into a short story, The Open Boat. The city engaged in legitimate commerce, too, and local merchants got rich trading in lumber, turpentine and cattle. The mansions they built are still standing, many lovingly restored Gilded Age masterpieces with heart pine floors, stained glass windows and acres of ginger bread trim. Walking down Centre Street from the waterfront, you pass through the city’s old commercial district, where many of the buildings date to the last decades of the 19th century. Turning south off of Centre onto any of the numbered cross streets takes you into the heart of the 50-square-block historic district where you’ll find example after the example of remarkable 19th century architecture. In particular, the Fairbanks House (at 7th and Cedar) is one of the few remaining examples of Italianate residential architecture left in North Florida. It’s now a bed and breakfast, so don’t be afraid to go up to the porch and knock. The Bailey House (7th and Ash) is a Queen Anne masterpiece while Villa Las Palmas (Alachua and 4th), a California Mission Style mansion shows the diversity of styles in Fernandina’s historic district.