Green’s Dictionary of Slang

to saunter.

c.1698

B.E. Dict. Canting Crew n.p.: How you Sail about? How you Santer about?

1. (orig. US) to attack, physically or verbally.

1856		‘Q.K. Philander Doesticks’ Plu-ri-bus-tah 69: Then again, like rowdy ‘Suckers,’ / ‘Sailing in,’ without regard to / Any of the laws of ‘Fancy.’ [Ibid.] 126: Then, at once, squared off at Cuffee, / Instantly ‘sailed into’ Cuffee; / And he whaled away at Cuffee.
1866		Night Side of N.Y. 85: Many a time we have seen Izzy [...] ‘sail in’ with the gloves.
1883		‘Mark Twain’ Life on the Mississippi (1914) 27: Sail in, Corpse-Maker!
1884		J. Harrison ‘Negro English’ in Anglia VII 266: To jes sail inter = to attack vigorously.
1891		Morning Advertiser 30 Mar. n.p.: John Harvey called William Tillman a liar 150 times,... and offered to lick him 104 times. At the 104th William... thrashed John. The verdict of the jury was that William ought to have sailed in an hour and a half earlier [F&H].
1903		Bulletin (Sydney) 2 July 36/2: [M]y four-in-hand shivered an’ ’eld their breaths when the villain bloke useter sail inter the decent coves.
1916		O.O. McIntyre New York Day by Day 21 Nov. [synd. col.] He spat on his hands and sailed into the annoyed bettor.
1914		Bulletin (Sydney) 8 Oct. 5: Italy: ‘I think it’s nearly time for me to sail in and hit him too!’.
1930		W.R. Burnett Iron Man 105: When Jeff climbed through the ropes [...] he sailed into him and had him groggy in the end of two minutes.

2. to launch oneself headlong on a course of action.

1865		Leaves from Diary of Celebrated Burglar 18/2: Jack replied that he did not care a — how tough it was. He would sail in if the others were ready.
1884		(con. c.1840) ‘Mark Twain’ Huckleberry Finn 225: That’s always your way, Maim — always sailing in to help somebody before they’re hurt.
1909		J. Ware Passing Eng. of the Victorian Era 13/1: Sail in (American-Eng.). Equivalent to ‘Go it’, and taking its place in England.
1915		Wodehouse Psmith Journalist (1993) 171: Billy had not inquired into the rights and wrongs of the matter: he had merely sailed in and rescued the office-boy.
1926		Wood & Goddard Dict. Amer. Sl.
1953		R. Chandler Long Good-Bye 232: The inquest was a flop. The Coroner sailed into it before the medical evidence was complete, for fear the publicity would die on him.

3. to arrive, to enter, esp. in a slow and measured manner.

1700		T. Brown Amusements Serious and Comical (1744) III 68: From thence I sailed into a Presbyterian Meeting near Covent-Garden.
1861		Thackeray Lovel the Widower 110: Lady B. sailed in at this juncture, arrayed in ribbons of scarlet [...] and other gimcracks ornamenting her plenteous person.
1881		‘Bill Nye’ Bill Nye and Boomerang 17: He sails into the jail yard just in time to take his part.
1885		Bulletin (Sydney) 11 Apr. 12/1: The boss of an obscure back-blocks’ weekly boldly remarks that ‘love makes fools of all men.’ Quite a mistake. Nature has done the work for most up-country editors long before love has had a chance to sail in.
1896		Linlithgowshire Gaz. 7 Mar. 8/1: Martins, on the ither han’, lets ye sail along easily and pleasantly.

4. to eat or drink; to consume eagerly.

1906

Sun. Times (Perth) 11 Mar. 4/8: We were drawing little water but we drew a lot of cork / We were sailing into swankey by the Spit.

see walk (backwards) up Holborn Hill under Holborn Hill n.