The Socratic Trail follows paths and country lanes with little traffic across rolling Surrey hills and the Sussex Weald making use of short stretches of the North Downs Way, Greensand Way, Sussex Border Path and the South Downs Way, with panoramic views along the journey to the sea. The walk was adopted by Croydon LB as its Millennium Trail.

Start at any point along Island Main Road and journey in either direction around the entire island to complete the full loop (roughly 30 miles). There is only a short stretch of where the Island Main Road is non-existent which is between Saint George Basseterre and the airport. The two popular main streets to make this cut and to join back on the Island Main Road are either F.T Williams Hwy or Wellington Rd; your choice!