The gaff cutter Cachalot was built in Folkestone, Kent, in 1898. Throughout her history, she has had a series of notable owners and has experienced periods of both extensive use and neglect. Initially, during the Dunkirk evacuation (Operation Dynamo), her skipper was a civilian named Spurling, based in Dunkirk. Although the exact ownership at that time remains unclear, it is known that in 1934 she was fitted with a Stuart Turner 2-cylinder, 6hp auxiliary petrol engine.

After World War II, Cachalot was owned by various individuals including two stockbrokers, a parson, and a Brigadier. She cruised extensively around Britain, the Baltic, the Red Sea, and the Mediterranean, earning a reputation for many fast passages. However, over time, successive owners undertook modernisation efforts that resulted in the removal of her original interior teak panelling, brass cabin lamps, copper running lights, and her unique square compass—an instrument of which the only other known example is held by the Science Museum.

Despite these changes, the vessel has experienced a revival under her current owners, Ian and Jen Kiloh, who have been meticulously restoring her to closely resemble her original, elegant condition.

Cachalot was featured individually on a series of stamps titled Little Ships of Dunkirk, issued by Palau in 2015 to commemorate the 75th anniversary of Operation Dynamo.

On 4 August 2017, after a decade-long restoration by her then-owner Steve Yates, Cachalot emerged from her tent on the banks of the River Deben at Tidemill Yacht Harbour, Woodbridge, Suffolk. Steve Yates first encountered the vessel in 2005 at The Suffolk Yacht Harbour, Levington, Suffolk, where he was captivated by her elliptical counter stern. After a year of sailing on the East Coast and planning maintenance, the cutter nearly sank at her berth in January 2006. A detailed inspection revealed rot in the arch board and beam shelf, as well as damage from excessive re-fastening of planks over the years. Consequently, in May 2007, the vessel was declared a restoration project.

The restoration proved extensive, involving the installation of a new ply deck, replacement of approximately 90% of the planking in larch, and renewal of the sternpost, stem, rudder, and bulwarks. Most of her frames were either replaced or sistered. The bowsprit, famously depicted flying the St George’s cross in Tom Cunliffe’s book Hand, Reef and Steer during the 1990 ADLS ‘Return to Dunkirk’, was also replaced. At launch, the original bowsprit was temporarily used as a mast to allow the vessel to be dressed overall. Her Yanmar engine was reconditioned, and some reclaimed teak from the old deck was repurposed to create new boards for the sole and cockpit. She was fitted with a new suit of Ratsey & Lapthorn sails, and the interior fit-out has been carried out in stages, nearing completion as of 2022.

Cachalot has sailed primarily along the English East Coast but has also been navigated in the Western Isles of Scotland and the Mediterranean. She participated in the 1990 ADLS ‘Return to Dunkirk’ event, where she was photographed by Tom Cunliffe with her mainsail triced.

In 2009, Cachalot received a restoration award from the Transport Trust, recognizing the quality and dedication involved in her preservation.