The Greater Chassahowitzka black bear population is the smallest documented in North America with fewer than 20 individuals. Its future depends on landscape linkages with other bear populations that are separated by denatured habitat. We used a Geographic Information System (GIS) to identify potential landscape linkages between this isolated population and six others in Florida. Pathway lengths ranged from 60–194 km with varying potentials for facilitating black bear dispersal. Each pathway incorporated 35–88% conservation land and encountered at least 11 dispersal bottlenecks. Even pathways that incorporated extensive conservation land encountered bottlenecks that make these linkages potentially unviable. All six pathways, however, passed through ≥95% core black bear habitat. Thus, the infrastructure for a conservation network is still largely intact. The Suwannee pathway provides the best opportunity to restore connectivity between the Greater Chassahowitzka Ecosystem (GCE) and a southward colonising bear population in the Big Bend region. However, intensification of development poses an immediate threat to maintaining connectivity between the GCE and other bear populations in Florida. Through immediate strategic planning and active conservation and restoration measures, many of the generated pathways can provide long-term connectivity. Least-cost path analyses can aid in the conservation of wide-ranging animals by providing managers with a science-based, empirically derived blueprint of potential landscape linkages.