According to Philip Freneau's biographers, an early disillusionment appears to have resulted from Freneau's first experiences at sea as well as from an abortive love affair that began on the island of Bermuda in 1778. Freneau left behind scores of poems which detail his years in the Caribbean, seven of which, after much revision, he grouped together in 1809 and linked directly to his experiences in Bermuda. And although it can be shown that Freneau, incorporated diverse biographical material into these poems, the resulting fiction demonstrates that the poet was able to transcend his own unhappiness through literary art. These seven poems, subsequently labelled the "Amanda" poems in honor of the woman they seem to celebrate, have been ignored by Freneau's critics, who often regard them as little more than conventional love verses. The present study challenges this assumption and attempts to demonstrate that the creation of the "Amanda" story was of central importance to Freneau. The research has included a linear comparison of the known variants of the "Amanda" poems and has found that although the series comprises only seven poems in its final format, it holds major clues to unlocking the mysterious forces which shaped Freneau's intellectual, emotional, and artistic maturity. The study examines not only the poems in the "Amanda" series but also many other poems with structural or thematic ties to the series. Since Freneau's experience in the West Indies is the most pervasive motif in his work, "Amanda" surfaces in numerous poems, and her image becomes a vehicle through which the poet tests a sequence of metaphysical abstractions. To Freneau, she first comes to represent unattainable beauty, then disappointment, and finally resignation. As such, the myth of "Amanda" is arguably more important to Freneau than her real-life model. Whoever she was, "Amanda" profoundly affected the poet, his philosophy, and his art; and her influence on him has been overlooked far too long.