Drive south on Interstate 75, and you know within seconds of entering Florida that this state is serious about its tourism. No opportunity to advertise to Florida’s visitors is missed. Floridians market to state outsiders like their lives depend on it.This is especially true today of Key West, the island at the southernmost tip of the United States that many know as Margaritaville. But the island’s history of attracting travelers goes so much deeper than a souvenier t-shirt and participation in an alcohol-laden Duval Crawl. From the day the railroad first reached the island, Key West has used its advertising to attract business people and families, tourists and transplants. It has struggled with the conflict between preserving its historic culture and making a destination attractive to the most transient visitors. Along the way, it has created unique advertising to showcase the beauty and charm of the island.Filled with examples of advertising through the ages, this overview of more than half a century of Key West travel will be equally informative for the historian and for the visitor to Key West who wants to learn more about this magical island.