High Quality Content by WIKIPEDIA articles! Sailing in Anguilla has a long and deep history, and is one of the defining characteristics of the island. The history of Anguillian sailing is often indistinguishable from the history of the island itself. Sailing craft date back to the Taino and Arawak peoples who inhabited Anguilla before the British Colonisation. However these craft have had little influence on the unique sailing practiced in Anguilla. Instead, it originated from the fishing vessels constructed and built locally after colonization and the subsequent collapse of the local plantation system to provide food and modest income to the inhabitants.