Current debates on entrepreneurial ecosystems have predominantly focused on well-developed ecosystems of cities, regions, or countries. However, there is a continuing dearth of evidence about peripheral entrepreneurial ecosystems, specifically those positioned in coastal areas. Traditionally, such places have built their economies on tourism, but for many such areas’ single sector specialisation poses an economic development trap, limiting the potential for high growth and technology entrepreneurship. This chapter examines economic development challenges of an emerging coastal entrepreneurial ecosystem by looking closer at an illustrative example of Cornwall and Isles of Scilly (CIOS) in the UK, one of the least competitive regions in the UK. The key implication from this chapter is in identifying natural strengths of the area to build more sophisticated and diversified entrepreneurial activity. In particular, coastal areas need to channel their entrepreneurship activity towards technology and growth-oriented ventures. This may require developing knowledge pipelines to other ecosystems.