Windsong is the only surviving David Hillyard sailing yacht to have participated in Operation Dynamo. As one of the few pure sailboats, rather than motor-sailors, Windsong was not ideally suited for evacuating troops from beaches. On 1 June, prevailing light airs and her small Ailsa Craig auxiliary engine limited her speed and maneuverability. Despite these challenges, she operated at considerable risk close inshore amid bombing, shellfire, and a multitude of vessels moving in every direction.

Unlike the majority of the 'Little Ships,' Windsong had not been requisitioned by the Royal Navy prior to Operation Dynamo. Her owner, Mr. G.L. Dalton, had laid her up for the duration at Hillyards yard in Littlehampton on the South Coast of England. However, following a broadcast request for all available craft, Mr. Dalton prepared Windsong for sea. On 31 May, he sailed her to Dover and reported at 18:40 that she was "ready for sea and able to take thirty passengers," a statement reflecting his valor and patriotism more than the vessel’s actual capacity.

Mr. Dalton was instructed to report to Ramsgate, where Windsong joined eleven other small craft. They were towed to Dunkirk by the trawler Kinder Star. According to Mr. Dalton’s account in David Divine’s book, their arrival was met with heavy dive-bomber raids, narrowly missing their trawler. They were ordered to cut adrift and retreat individually. Windsong returned to Dover at 21:15 on 2 June.

At this point, command of Windsong was transferred to T.H. Falkingham and A. Barden, whose exact status—whether naval ratings or fishermen recruited for the operation—is unclear. Mr. Dalton, having been without sleep for over 48 hours, was likely unfit for another Channel crossing. The replacement crew’s efforts were later recognized in a document praising their voluntary service and deserving of medals.

Following Operation Dynamo, Windsong was formally taken over by the Royal Navy. Alongside the vessel Sundowner, she was deployed to Brightlingsea on the East Coast. Under the command of Mr. Birtwhistle, a solicitor called up for the duration, Windsong served as a patrol and mine-spotting vessel in the Thames Estuary.

Mr. Dalton did not retain ownership long after the war. By 1950, Windsong was employed as a charter yacht. During one charter, she encountered severe weather in the English Channel. With all but the mizzen sail blown out and the auxiliary engine inoperative, the skipper raised a distress signal. The 600-ton German freighter SS Feronia responded and, after a struggle, passed a tow-line. During this operation, the Feronia’s counter struck Windsong’s stem post, causing damage that remains visible. Despite the tow-line parting twice, Windsong was successfully towed at five knots into the Solent. This event attracted press attention, as the Feronia was the first German ship to enter Spithead since the end of the Second World War.

Windsong’s fifth owner, as recorded in her ‘Blue Book,’ was Lady Effie Millington-Drake, wife of Sir John Millington-Drake, the British representative in Buenos Aires during the Battle of the River Plate. Sir John played a key role in delaying the departure of the German battlecruiser Graf Spee from Montevideo through a series of deceptive radio messages. This enabled the Royal Navy to reinforce Admiral Harewood’s cruiser force, which successfully engaged the Graf Spee when she left neutral waters. The Graf Spee was ultimately scuttled at the mouth of the River Plate to prevent capture by British forces.

The current and thirteenth owner of Windsong is Colonel (Retired) M.N.V. Duddridge, OBE, who acquired the vessel in 1986. For six years, he moored Windsong in Holland and sailed extensively in Dutch waters and along the East Coast of England. In 1992, he and his wife sailed Windsong from her winter mooring on the River Maas to Cyprus in the Eastern Mediterranean. With the masts lowered, the first month was spent navigating the rivers and canals of Belgium and France, including passage through 209 locks. At Marseilles, the masts were stepped, and for the following two months Windsong attracted attention throughout the Mediterranean, visiting locations such as Elba, Capri, the Corinth Canal, and the Greek islands of the Aegean Sea.

Seven years of exposure to the Mediterranean sun caused Windsong’s timbers above the waterline to dry and shrink significantly. A major refit ashore was recently completed, including re-caulking and a completely new paint scheme. These efforts have restored Windsong to her former glory, befitting the sole representative of the Association of Dunkirk Little Ships in the easternmost corner of the Mediterranean.