During America’s Gilded Age, wealthy Americans found respite from industrialized cities at resort hotels in picturesque destinations across the country. Beginning in the mid-1880s, Henry Flagler sought to transform the historic city of St. Augustine into an alluring winter paradise akin to Italy, Egypt, or Spain.

Flagler’s St. Augustine hotels operated seasonally, remaining open for a limited period each year, typically from November through April. During this short window, the hotels offered an enticing array of entertainments to attract wealthy tourists from colder climes in the north who would often stay for the whole season.

During the day, guests met and mingled on verandas and terraces, and relaxed amidst landscaped courtyards and grand parlors. They partook in bowling, bicycling, tennis, and swimming, and a variety of adventurous daytrips organized by the hotels—nearby Anastasia Island’s beaches, lighthouse, and Alligator Farm were popular attractions for visitors. In the evenings, guests enjoyed grand dinners, elaborate balls, and theatrical entertainments hosted onsite at the hotels.