The Windsor Hotel was built in 1875, catching Jacksonville’s tourist boom with a firm grasp. A renowned vacation spot for those looking to escape the cold, Jacksonville saw an average of 50,000 to 73,000 visitors on a yearly basis at the time. The Windsor also was opened to soldiers awaiting orders to Cuba during the Spanish-American War in 1898. Deemed one of Florida’s finest hotels and prized for its unusual architecture, the three-story hotel featured a lavish dining hall complete with an extravagant centerpiece and balcony, spacious rooms, office space, parlors, and a golf course tucked amidst scenic Florida nature.
Built entirely out of wood, the hotel sustained significant damage during the Great Fire of 1901. Owners Abbie Dodge and Frank Cullen constructed a new brick, stone, and steel in a “magnificent Spanish Renaissance style to cover the entire block between Hogan, Monroe, Duval, and Julia streets,” as reported by the Times-Union in 1966. The revamped Windsor featured a red tiled roof, grand columns, and birch and mahogany woodwork.
A brochure put out by the Hotel Windsor said, “The views in this booklet show you the delightfully unusual character of the building and environments, but only a stay at the WINDSOR can bring you a realization of the pleasures to be derived from a Winter in Sunny Florida. Our service is nearly as perfect as we can make it. Our desire—to help you enjoy Jacksonville and Florida.”
Reopened in 1902, it became a hotspot for royalty, celebrities, and presidents, notably Franklin D. Roosevelt, who visited in 1933. Several organizations also held their first meetings in the hotel including the Women’s Club of Jacksonville in 1895, as well as the Jacksonville Rotary Club in 1912, and the Kappa Kappa Gamma Alumni Association in 1942.