• WordNet 3.6
    • v outsail sail faster or better than "They outsailed the Roman fleet"
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Webster's Revised Unabridged Dictionary
    • v. t Outsail To excel, or to leave behind, in sailing; to sail faster than.
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Century Dictionary and Cyclopedia
    • outsail To sail faster than; leave behind in sailing.
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Chambers's Twentieth Century Dictionary
    • v.t Outsail owt-sāl′ to leave behind in sailing.
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In literature:

We soon perceived that she could outsail our brig and if the wind held would escape.
"The Martin Luther King, Jr. Day, 1995, Memorial Issue" by Various
Donald had confidently asserted his belief, weeks before, that she would outsail the Skylark, not as a mere boast, but as a matter of business.
"The Yacht Club" by Oliver Optic
He had outsailed his rival from St. Helena.
"Freaks of Fortune" by Oliver Optic
He admitted that we could outsail him, for he had done his best to keep up with the Sylvania.
"Up the River" by Oliver Optic
As Dory continued on his course, he was satisfied that he was greatly outsailing the boat from which he expected trouble, if he had any.
"All Adrift" by Oliver Optic
We'll outsail 'em yet.
"The Ocean Waifs" by Mayne Reid
Nothing on the coast could outsail the sloop, he was sure.
"The Black Buccaneer" by Stephen W. Meader
They can outsail us and keep ahead of us; and they'll undersell and overbuy us wherever we go.
"Billy Topsail & Company" by Norman Duncan
We shall then outsail everything, go where we like unsuspected, and land our cargo with ease.
"The Pirate and The Three Cutters" by Frederick Marryat
When I am with you we shall cut the boat adrift and let the vessel outsail us.
"In the Days of Drake" by J. S. Fletcher
Its commander, Admiral Hood, had followed sharply after De Grasse, and had outsailed him.
"Hero Stories from American History" by Albert F. Blaisdell
We lay more and more to the nor'ard; and you would have thought the shore copied our manoeuvre and outsailed us.
"The Works of Robert Louis Stevenson - Swanston Edition Vol. 18 (of 25)" by Robert Louis Stevenson
Off like a bird she went, now quite outsailing her pursuer.
"Stories of Our Naval Heroes" by Various
They were like enough to carry the ebb-tide with them to the capes or even to outsail it.
"The Red City" by S. Weir Mitchell
The wind being light, they outsailed my vessel until I lost sight of them.
"Journal of Voyages" by Jacob Dunham
I take it you somehow managed to outsail the Gloucester.
"Caribbee" by Thomas Hoover
We were several times chased in our passage, but outsailed everything; and in thirty days had soundings.
"Memoirs of Benjamin Franklin; Written by Himself. [Vol. 1 of 2]" by Benjamin Franklin
Porter saw that his vessel could outsail the enemy, but he was not anxious to escape.
"The Second War with England, Vol. 2 of 2" by Joel Tyler Headley
We can outsail you some, and we shall get to Stoneland before you do.
"The Rival Campers Afloat" by Ruel Perley Smith
One outsailed him; he captured the other after much struggle.
"God Wills It!" by William Stearns Davis