Start your tour at Piazza del Duomo, Milan’s beating heart, dominated by the awe-inspiring Duomo di Milano, a Gothic masterpiece with its spire-crowned façade. Marvel at the cathedral’s intricate details or, if time allows, pop in for a quick peek at its soaring interior (entry to the main area is affordable). From here, stroll north through the Galleria Vittorio Emanuele II, an opulent 19th-century shopping arcade with a glass-vaulted roof, evoking Milan’s elegance.
After about 10 minutes, exit the Galleria onto Piazza della Scala, home to the world-renowned Teatro alla Scala, Milan’s historic opera house. Nearby, stop at Peck (Via Spadari, 9), a historic gourmet deli since 1883, perfect for a quick lunch of artisanal panini, prosciutto, or creamy risotto. It’s a bustling spot, no reservations for the casual counter, so arrive early to avoid queues.
Continue north along Via Alessandro Manzoni, a chic street lined with designer boutiques, towards the Quadrilatero della Moda, Milan’s fashion district. Wander through Via Montenapoleone, where high-end shops like Armani and Prada showcase the city’s sartorial fame. For a cultural touch, pop into the Museo Poldi Pezzoli (Via Manzoni, 12), a gem of a museum with Renaissance art and ornate interiors, ideal for a quick 20-minute visit.
Head back south towards Via Dante, a lively pedestrian street, and stop at Caffe Cova (Via Montenapoleone, 8, or its newer outpost at Via Dante, 10), a historic patisserie since 1817, for an espresso or hot chocolate paired with a delicate pasticcino (small pastry). It’s a classic Milanese experience, no bookings needed, but expect a lively crowd.
Continue along Via Dante to Castello Sforzesco, a grand 15th-century fortress with sprawling courtyards. If you have time, dip into one of its museums (like the Museum of Ancient Art) for a quick look at Michelangelo’s Pietà Rondanini. From here, stroll through Parco Sempione, a green oasis, towards the Arco della Pace, a neoclassical triumphal arch that’s a perfect photo stop.
Loop back towards the centre via Corso Magenta to reach Santa Maria delle Grazie, home to Leonardo da Vinci’s The Last Supper (booking required for the mural, so admire the church’s exterior if you haven’t pre-booked). Nearby, stop at Pasticceria Marchesi (Via Santa Maria alla Porta, 11a), another historic patisserie, for a creamy cappuccino or a slice of panettone, Milan’s iconic sweet bread. It’s a no-reservations spot, so arrive promptly.
End your tour at Piazza Santo Stefano, a charming square near the Duomo, where you can relax at a café like Bar Magenta (Via Carducci, 13), a historic haunt since 1907, serving aperitivi with a Milanese flair. Soak up the city’s cosmopolitan vibe as you unwind.This 3-4 km route captures Milan’s architectural grandeur, culinary heritage, and fashion-forward spirit, perfect for a four-hour stroll. Wear comfortable shoes for the cobbled and paved streets
