This study examined the relationship between transportation support and self-regulatory driving behaviors of 566 community-dwelling older adults living in retirement communities, with a focus on gender differences. The results of logistic regression analysis showed that older women were more likely to avoid driving at night or on the highway than their male counterparts. Transportation support from peer friends was found to increase the likelihood of self-regulatory driving behaviors. The findings of this study imply that transportation policy and driving safety programs for older adults need to be developed, considering available transportation alternatives and gender differences in driving behaviors.