His education included attending Marlborough and RAF College Cranwell, where he enrolled directly after school. Jonathan pursued sailing and racing during his career in the Royal Air Force (RAF), seizing opportunities when not engaged in flying duties. Following 22 years as a fighter pilot and instructor, he spent seven years in Whitehall at the Ministry of Defence (MoD) and Cabinet Office, which afforded him time to cultivate a serious interest in sailing.

In 1977, Jonathan purchased his first sailing cruiser, based in Tollesbury, and extensively sailed the English Channel until 1982 when he was stationed in Naples. There, the RAF permitted him to sail his boat, allowing him to spend four summers exploring the Mediterranean, particularly the Tyrrhenian Sea. Upon returning to the UK, he sold the boat and retired early from the RAF in 1985.

Subsequently, Jonathan served as the Secretary of the Royal Lymington Yacht Club until 1998, when he retired for the second time and was invited to become an Honorary Member. He acquired a larger boat and sailed it from Lymington for three decades, undertaking voyages such as Amsterdam to the Scillies, circumnavigating Britain and Ireland, and continuing Mediterranean cruising with friends from Minorca to Kos.

Although he retired from boat ownership in 2015, Jonathan continued to sail occasionally with his sons. At the age of 89, he was called upon by his sons to participate in the ARC 2024, making him the oldest participant. His adventures have taken him 5,500 miles since October 2, 2023, earning him recognition on Spanish television and in the American yachting press.