The first point of interest is that when describing the places he has already been, the speaker mentions "western islands." The connotation of "western" in a context of exploration is at least two-fold. Since the western world is suggestive of civilization or what is "known" in western thought, it seems that "western islands" may be a reference to the Mediterranean islands of Greece, or perhaps western thought more generally, as opposed to pre-industrial cultures that the west has encountered in its explorations. This is dramatically opposed to the other obvious connotation of "western islands": the new world itself. While opposing the previous reading, this reading also suggests that perhaps the speaker is establishing his familiarity with the new world, hinting that the frontiers of the globe have been exhausted, in contrast with the intellectual frontiers that have been opened by Chapman's Homer.
Keat's "watcher of the skies" supports the second reading of "western islands," and is the second part of the poem that catches my eye. The speaker moves beyond simple geographical exploration to the exploration of something completely other. This transition from terrestrial to astronomical mirrors the rapid transition from knowledge to discovery, just as it mirrors the transition from familiar surroundings to the otherness of space.
Thirdly, and perhaps most importantly, Keats has reopened the possibility of fertile exploration even of things already known when he introduces near the end of the poem his "wild surmise." It seems that although the new world Cortez and his men look on is itself wild and new, there is also something wild in their own speculation and imagination. This in turn would suggest that while exploring something new is invigorating and important, the creative imagination can introduce an element of wildness into even those things which we have already studied, just as the speaker has no doubt studied Homer and other masterpieces of western thought. The transition from geographical to astronomical has been extended yet again to the psychical; the frontiers have been pushed back so far that they are now internal to the human mind.
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