schooner (n.) Look up schooner at
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.