Well known as the oldest city in North America, St. Augustine’s transportation infrastructure was developed prior to the rise of automobiles. Limited waterway crossing routes, constrained rights of way, and congested traffic patterns have further made this city a challenging place for bicycling. The bike plan identifies opportunities for improved bicycling conditions within St. Augustine, allowing residents and visitors to explore this historic city in a new, healthy and exciting way. A very successful public outreach element assisted with route and destination identification for this plan. With over one hundred participants, this included interactive workshops at the local weekly farmers’ market and in the downtown historic district. Additional public input was gathered through web-based response and local media outreach. The plan includes recommendations to increase bicycle accommodation on the principal roadways and bridges that carry riders into the city and also identifies alternative local routes that will allow for more relaxed exploration away from the most congested roads. A uniform way-finding system assists bicyclists in navigating designated routes to popular destinations. The plan also identifies promising bicycle parking locations and also makes recommendations based on the analysis of local crash reports.