The rapid adoption of location tracking and mobile social networking technologies raises significant privacy challenges. Today our understanding of people's location sharing privacy preferences remains very limited, including how these preferences are impacted by the type of location tracking device or the nature of the locations visited. To address this gap, we deployed Locaccino, a mobile location sharing system, in a four week long field study, where we examined the behavior of study participants (n=28) who shared their location with their acquaintances (n=373.) Our results show that users appear more comfortable sharing their presence at locations visited by a large and diverse set of people. Our study also indicates that people who visit a wider number of places tend to also be the subject of a greater number of requests for their locations. Over time these same people tend to also evolve more sophisticated privacy preferences, reflected by an increase in time- and location-based restrictions. We conclude by discussing the implications our findings.