Bob Hilton was commissioned into the army in 1936 but was severely injured shortly thereafter and subsequently medically discharged. At the outbreak of war, he volunteered again and was soon selected for officer training. However, upon receiving his second commission, it was discovered, and he was discharged once more.

In May 1940, Hilton volunteered to take any available ship to Dunkirk. The authorities required crews of three, but he had only one companion, a ginger-haired man named Shaw. They resolved this by offering a drink or two, plus £1 in cash, to a longshoreman at Tilbury to sign on. They were told he could disappear afterward if he chose not to participate.

They were assigned the Ryegate II, which was found to be laden with jerry cans—some containing water, others sealed and containing petrol. On a pleasant late May evening, they reached Ramsgate and went ashore to obtain supplies. The Women's Voluntary Service (WVS) had ample food but lacked utensils, so they borrowed glasses from a pub before setting out for Dunkirk.

Hilton recalled the scene: "It was just like Piccadilly Circus. There were masses of ships going to and fro. There was no need to navigate; we just followed the others. We focused on the task, which was to sail as close as possible to the shore, pick up all we could carry, and ferry them out to the off-lying ships."

After some time, the engine began to seize, and as the tide receded, they tied up behind a ship named Horst and used its lifeboat to row ashore to collect soldiers. Several times, the boat capsized when men wading in water up to their armpits grabbed the gunwales to board. Eventually, they were ordered to return home, packed like sardines in a small steamer.

Ryegate II was towed home and upriver at the end of a line of Little Ships by a tug. Following Dunkirk, Bob Hilton joined the Navy, received the King’s commission for the third time, and was awarded the Distinguished Service Cross as Lieutenant Commander RNVR.

The vessel previously belonged to David and Elizabeth Pamment, who took her to the commemorative return to Dunkirk in 1985. As of November 2016, Ryegate II was sold to a new owner and transported by road to Hamburg, where she underwent an extensive rebuild and the fitting of a new 90hp engine. She was scheduled to remain out of the water until at least August 2018, with plans to visit the Royal Netherlands Yacht Club near Muiden, Amsterdam. The owner hoped to see her return to the fleet for the 2020 commemorative event.