The recent invention and popularity of mobile navigation devices have increased the possibility of unplanned, serendipitous travel. To better understand the independent travel market, this study developed a scale for the construct “Style of Independent Travel” (SIT) in order to explore the serendipitous and organized dimensions of travel and their relationship to relevant travel behavior. The scale was included in a survey of visitors to the Rocky Knob area of southwest Virginia. Findings revealed that tourists had a higher preference for travelling spontaneously than following a fixed and organized itinerary and that serendipity and organization in travel was related to travel planning and visitor activities. However, there was no significant relationship between SIT, past visitation, and role of the destination as primary destination or stopover.