The poem's structure is a day-in-the-life: evening (nightingale, moon, curfew bell), midnight study (lamp in tower, reading Hermes and Plato), tragedy performance, dawn (civil-suited morning), day (twilight groves, hidden brooks), ending with old age in a hermitage. Milton's designing an ideal contemplative existence.
Night study is the core: 'out-watch the Bear' means staying up past the constellation's setting—all-night reading sessions. He wants to read Hermes Trismegistus (occult philosophy), Plato (what happens to souls after death), texts about daemons (spirits that mediate between divine and earthly realms). This was serious Renaissance intellectual work, not casual reading.
The tragedy section lists Greek plays (Thebes = Oedipus; Pelops' line = House of Atreus; Troy = Homer) and wishes dead poets could return. Musaeus was a mythical poet; Orpheus descended to Hades and moved Pluto to tears with his music. Milton wants Melancholy to resurrect Chaucer ('him that left half told / The story of Cambuscan bold')—the Squire's Tale with its magic ring, mirror, and brass horse.
'Where more is meant then meets the ear'—this line is Milton's aesthetic principle. He wants art with hidden meanings, allegory, depth. The whole poem is about preferring complexity and solitude to simple pleasures. It ends in a hermitage studying astronomy and botany until he achieves 'something like Prophetic strain'—the goal is mystical knowledge through contemplative discipline.