This paper investigates how social dimensions may shape the experiences, perceptions, and preferences of winter visitor tourists, also known as “snowbirds.” This research compares members of the two primary snowbird generational cohorts, Baby Boomers and the Silent Generation, to explore possible differences in activity participation, travel party features, and destination satisfaction. Focusing on a popular winter destination in the Southwestern United States, this research integrates two winter visitor samples, one consisting of seasonal residents at recreational vehicle (RV) and mobile home parks, and the other consisting of seasonal homeowners who do not live in an RV or mobile home park environment. The implications of similarities and differences between groups’ activity participation rates, travel party characteristics, and perceived satisfaction with the destination are discussed.