Seasonality is an essential factor influencing tourism demand and traveler behavior at the destination. As such, seasonality (i.e., the influx of tourists) needs to be managed by destination marketing organizations. Most tourism studies have focused mainly on the forecasting methods/metrics and the effect of seasonality at the aggregate level rather than understanding seasonal differences in the nature of the traveler and travel experience. The purpose of this study is to understand seasonality at both the aggregate market level and individual traveler level. As such, this study first utilizes the concept of the gravity model to understand seasonality in the number of inquiries through an official website. This study, then, uses seemingly unrelated regressions to estimate simultaneously the effect of various trip-related factors on overall trip expenditures and the length of the trip. The results show that the impact of seasonality on aggregated demand is surprisingly consistent across the seasons; however, individual-level analyses indicate that traveler behavior and travelers' responses to advertising differ significantly across seasons. Thus, destination marketers need to understand the nature of seasonality of their specific markets more accurately to provide appropriate tourism products/services to their current and potential travelers.