Skylark was constructed in 1922 by John I Thornycroft at Hampton-on-Thames for D. Melville Wills of Bristol and the Kyle of Lochalsh. The vessel was intended to cruise between Wills' two estates. After being sold in 1926, Bristol remained Skylark's home port until the outbreak of World War II.

By 1939, Skylark was laid up on the Thames and subsequently commandeered by the Ministry of War Transport. During the war, she participated in Operation Dynamo, the evacuation of Allied troops from Dunkirk, under the command of Sub-Lieutenant M.J.R. Yeatman. Skylark sustained damage to her steering from enemy fire and was abandoned. She was later found drifting off Dunkirk and was towed back by the vessel Southern Queen, commanded by Basil de Matos, with assistance from the Eastbourne Lifeboat, Jane Holland.

Following this, Skylark remained in government service, performing harbour patrol and pilotage duties until 1947. Afterward, she returned to cruising along the coasts of southwest England and Wales and was renamed Tahilla.

In 1957, the vessel was relocated to the Mediterranean, where she cruised extensively for ten years. Subsequently, she was laid up in Menton and fell into a state of disrepair. The current owners acquired Skylark in 1969 and initiated restoration efforts, which have continued to the present day.

Skylark returned to the United Kingdom in 1980 and is currently based on the Hamble River, from where she cruises the south coast of England and North European ports.

The original engines were Thornycroft petrol/paraffin motors; however, in 1966, two Gardner 4LK engines were installed—one built in 1928 and the other in 1932. There are no plans to replace these engines.