Walking for physical activity can bring important health benefits to older adults. In this population, walking has been related to various urban design features and street characteristics. To gain new insights into the microscale environmental details that might influence seniors' walking, details which might be more amenable to change than neighbourhood level factors, we employed a reliable streetscape audit tool, in combination with Google Street View™, to evaluate the 'walkability' of where older adults choose to walk. Analysis of the routes selected by a purposive sample of independently mobile adults aged 65 years and over living in Edinburgh, UK, revealed a preference to walk in more walkable environments, alongside a willingness to walk in less supportive settings. At times, factors commonly considered important for walking, including wayfinding and legibility, user conflict, kerb paving quality, and lighting appeared to have little impact on older adults' decisions about where to walk. The implications for policy, practice, and the emerging technique of virtual auditing are considered.