This study aims to reconcile two contrasting research perspectives on tourist decision making. The first perspective contends that tourists are constrained with limited resources and are inhibited to travel, whereas the second perspective contends that tourists search for means to develop a career in traveling and are thereby intrigued to travel to more destinations. This study employs a multilevel design by assessing the relationships of tourist travel frequencies among three outbound markets, namely, in-state, out-of-state domestic, and international markets, through a longitudinal study. By modeling a situational factor—unemployment rate—at the macro level, this study reveals a significant cross-level moderating effect on the relationship between the travel frequencies of domestic and international markets. The findings not only reveal which of these two perspectives is more applicable at a particular situation but also enrich the theories germane to travel career, destination choice, and distance decay.