Rum-running , or bootlegging, is the illegal business of transporting ( smuggling ) alcoholic beverages where such transportation is forbidden by law. Smuggling is usually done to circumvent taxation or prohibition laws within a particular jurisdiction. The term rum-running is more commonly applied to smuggling over water; bootlegging is applied to smuggling over land. According to the PBS documentary Prohibition , the term "bootlegging" was popularized when thousands of city dwellers would sell liquor from flasks they kept in their boot leg all across major cities and rural areas.   The term "rum-running" most likely originated at the start of Prohibition in the United States (1920–1933), when ships from Bimini in the western Bahamas transported cheap Caribbean rum to Florida speakeasies . But rum 's cheapness made it a low-profit item for the rum-runners, and they soon moved on to smuggling Canadian whisky , French champagne , and English gin to major cities like New York City and Boston , where prices ran high. It was said that some ships carried $200,000 in contraband in a single run.