People actively select their environments, and the environments they select can alter their psychological characteristics in the moment and over time. Such dynamic person-environment transactions are likely to play out in the context of daily life via the places people spend time in (e.g., home, work, or public places like cafes and restaurants). This article investigates personality-place transactions at 3 conceptual levels: stable personality traits, momentary personality states, and short-term personality trait expressions. Three 2-week experience sampling studies (2 exploratory and 1 confirmatory with a total N = 2,350 and more than 63,000 momentary assessments) were used to provide the first large-scale evidence showing that people's stable Big Five traits are associated with the frequency with which they visit different places on a daily basis. For example, extraverted people reported spending less time at home and more time at cafés, bars, and friends' houses. The findings also show that spending time in a particular place predicts people's momentary personality states and their short-term trait expression over time. For example, people reported feeling more extraverted in the moment when spending time at bars/parties, cafés/restaurants, or friends' houses, compared with when at home. People who showed preferences for spending more time in these places also showed higher levels of short-term trait extraversion over the course of 2 weeks. The findings make theoretical contributions to environmental psychology, personality dynamics, as well as the person-environment transactions literature, and highlight practical implications for a world in which the places people visit can be easily captured via GPS sensors. (PsycInfo Database Record (c) 2021 APA, all rights reserved).