Wake at Café Doria for espresso near the Duomo, spend morning inside the Cathedral and climb its rooftop terraces. Lunch at a hole-in-the-wall trattoria on Via Spadari, wander the fashion district around Via Montenapoleone, then settle into aperitivo at a Navigli-side bar by sunset with a Negroni.

Start with espresso at Cafe Fernanda on Via Brera, then spend 2 hours in Pinacoteca di Brera's Caravaggio room. Lunch at a standing bar like Bar Magenta for panini, wander the gallery-dense backstreets (Via Fiori Chiari, Via Madonnina), and by 6 PM join the aperitivo crowds spilling onto Via Brera itself. Dinner at a family trattoria like Trattoria Masuelli San Marco, then hunt for live jazz in one of the basement wine bars.

Start with espresso at Café Nero in the morning calm, then browse Via Torino's vintage and design shops. Lunch at a risotto spot like Ripa di Navigli. Afternoon stroll along the Navigli canals (Navigli Grande, Navigli Pavese) to Parco Sempione. Return for early-evening aperitivo on a terrace, then dinner and late drinks as the neighbourhood transforms after 10pm.

Start with espresso and cornetto at a neighbourhood bar, explore Giardini Pubblici Indro Montanelli for greenery and cool air, lunch at a trattoria on Via Lecco. Afternoon museum browsing at Civica Galleria d'Arte Moderna, then wandering Via Torino's indie shops. Evening aperitivo at one of the cramped standing bars, dinner at a family-run osteria, and nightlife crawl along Corso Buenos Aires.

Start with espresso at Café Bilingue on Via Messina, wander the Navigli Canal for street art, lunch at Ratanà for fresh pasta. Afternoon explore Padiglione d'Arte Contemporanea, then aperitivo at a Corso Como rooftop overlooking the neighbourhood. Finish with late dinner at a Via Torino tratoria where locals congregate.