Storytelling about places is recognized as a tool to enhance the reputation of regions as they compete for tourism and economic development spending in the digital age. Through digital media, people can be encouraged to tell their tourism stories and share their experiences. Our design approach integrates Service Science, Management, Engineering, plus Design, Arts and Public Policy (SSME + DAPP, so just SS) and Viable Systems Approach (VSA) perspectives. Storytelling can be managed in a local service system to enhance brand competitiveness. The way local governments and cultural organizations understand and encourage storytelling about places (“place storytelling”) can have a significant impact on the success of a region competing for tourism and development spending. Place storytelling enables local stakeholders to tell their personal stories about their beloved places. Our analysis and cases demonstrate that place storytelling enables strategic communication that supports sustainable competitive advantage. By means of an analysis of “Umbria on the Blog” which is an innovative project which joins place and web 2.0, and “Il Mangiastorie” which promotes wine and food and tourism of some Campania internal area, we highlight the relevance of managing place storytelling as a strategic communication involving stakeholders in the place-identity-building process. This paper presents a model of place storytelling that local governments and cultural organizations can use to encourage and manage stakeholder engagement in a multilevel process for improving regional service system marketing and communications in the digital age.