In the Akalabęth it is stated that they sail round the south of Middle-Earth:
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Thus it was that because of the Ban of the Valar the voyages od the Dúnedain in those days went ever eastward and not westward, from darkness of the North to the heats of the South, and beyond the South to the Nether Darkness; and they came even into the inner seas, and sailed about Middle-earth and glipsed from thier high prows the Gates of Morning in the East. ...
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Respectfully
Findegil