Aesthetics constitute a fundamental element of the tourist experience and contribute to tourists’ behavioral intention. Yet, empirical research on destination aesthetics is very limited. This study explores whether destination aesthetics affects behavioral intention and whether there is a difference between tourists’ aesthetic judgment and aesthetic distance. Destination aesthetics are determined by comparing the perceived difference between the home environment of the tourist and the destination. Gestalt theory has been adopted to understand the impact of destination aesthetic judgment and aesthetic distance on behavioral intention. Structural equation modeling was the main analytical tool used to assess the results. A t-test was also performed. In this research, the behavioral intention of tourists (word-of-mouth intention, willingness to pay, and revisit intention) is positive when tourists perceive environments of holiday locations to be better kept than their accommodations. It has been determined that aesthetic distance only significantly and negatively affects willingness to pay. Among tourists coming to Istanbul, the research found locale characteristics, scope, and perceived age to be important determining factors of destination aesthetics, whereas with tourists coming to Antalya, the research defined destination aesthetics in terms of scope, upkeep, accord, perceived age, and shape. This study shows how destination managers could leverage the aesthetic experiences of tourists.