After initial success as prizemaster of the American privateer Algonquin, passing as master's mate, and a period as Acting Lieutenant, Drinkwater survived the sinking of HMS Royal George but lost his chance of a commission as a result of Admiral Kempenfelt's death, instead providentially finding employment as a mate on Trinity House yachts.
Subsequently re-employed as a master's mate, he found himself serving in HMS Kestrel, a cutter on special service in the English Channel, in which he first encountered Hortense Santonax nee Montholon, who haunted his imagination for decades thereafter, and with whose husband Eduard Santhonax, a talented and ruthless Bonapartist naval officer, he found himself recurrently in conflict over the following years.
His commission as Lieutenant was confirmed by Admiral Duncan following Kestrel's action with a French yacht on the periphery of the Battle of Camperdown.
Moving with Kestrel's irascible Welsh captain Madoc Griffiths to brig HMS Hellebore, Drinkwater was sent to eh Red Sea by Admiral Lord Nelson, only to lose Hellebore on Daedalus Reef but gain French frigate Antigone in a cutting out operation.
Drinkwater was given command of bomb vessel tender HMS Virago as part of the British expedition to Copenhagen to neutralise the Danish fleet, and managed to attract the support of both Admirals Parker and Nelson as a result of his assistance in surveying the battleground.