Etymology
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schooner (n.)

fore-and-aft rigged vessel, originally with only two masts, 1716, perhaps from a New England verb related to Scottish scon "to send over water, to skip stones." Skeat relates this dialectal verb to shunt. Spelling probably influenced by Dutch, but Dutch schoener is a loan-word from English, as are German Schoner, French schooner, Swedish skonert. Said to have originated in Gloucester, Mass., shipyard.

The rig characteristic of a schooner has been defined as consisting essentially of two gaff sails, the after sail not being smaller than the fore, and a head sail set on a bowsprit. [OED]

Meaning "tall beer glass" is from 1879, of unknown origin or connection.

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Definitions of schooner

schooner (n.)
a large beer glass;
schooner (n.)
sailing vessel used in former times;
From wordnet.princeton.edu