Born in Jersey, the largest of the Channel Islands, Oakleigh later moved to Northern Ireland, where she spent her formative years before relocating to Brighton and joining the Combined Cadet Force (CCF). She credits this experience with building her confidence and fostering her passion for adventure and travel. Her dedication to customer service was recognized early on when she received an award for outstanding service, leading to an opportunity to manage The Anchor Club, a fine dining restaurant in Jersey. It was there that she first became aware of the opportunities within the yachting industry. After completing two successful seasons,
akleigh took time to further develop her skills and experiences by travelling through Africa and Southeast Asia.