Milan’s story stretches from Roman Mediolanum to the Visconti and Sforza courts, where Leonardo da Vinci sketched inventions and painted The Last Supper. Today, the city fuses Gothic spires and Renaissance masterpieces with cutting-edge design, fashion, and cuisine.

In two days, you’ll stand atop the Duomo’s marble rooftop, wander Brera’s cobbled lanes, admire Sforza Castle, and toast the evening along the Navigli canals. Expect world-class art, refined Milanese kitchens, excellent espresso, and a tram network that’s part transport, part time machine.

Practical notes: reserve Last Supper tickets weeks in advance, and observe church dress codes (shoulders/knees covered). Most museums close on Mondays; the Metro is fast and safe (single rides about €2.20; 24-hour pass about €7.60). Milan has three airports—Linate (close in), Malpensa, and Bergamo—each with straightforward transfers.

Milan

Italy’s fashion capital is also a heavyweight for art and architecture. The Duomo took nearly six centuries to complete; Galleria Vittorio Emanuele II introduced glass-and-iron “cathedral of commerce” grandeur; and modern Porta Nuova shows the city’s green future with the vertical forest, Bosco Verticale.

Top highlights include the Duomo and rooftop terraces, Leonardo’s Last Supper at Santa Maria delle Grazie, the Pinacoteca di Brera, Sforza Castle and Parco Sempione, La Scala Opera House, and the canal-side Navigli district—ideal for aperitivo culture born in Lombardy.

• Where to stay (Hotels.com affiliates): Hotel Principe di Savoia (classic Milanese grandeur, pool and spa), Room Mate Giulia (steps from the Duomo, design-forward), UNAHOTELS Cusani Milano (between the Duomo and Sforza Castle), Ostello Bello (social, central, great for budget travelers). Browse more options on Hotels.com or apartments on VRBO.
• Getting to Milan: For flights within Europe, compare fares on Omio (flights). For trains across Italy and Europe (e.g., Rome–Milan ~3h, Florence–Milan ~1h55, Venice–Milan ~2h25), check Omio (trains). For long-haul or non-Europe flights, search Trip.com (flights).

Day 1 — Arrival, Brera Stroll, and Navigli Aperitivo

Morning: Travel to Milan. From Linate Airport, take the M4 Metro ~15 minutes to San Babila (central). From Malpensa, the Malpensa Express train is ~50–55 minutes to Cadorna or Centrale. From Bergamo (Orio al Serio), coaches to Milano Centrale take ~50–60 minutes. If you’re arriving by rail, most high-speed trains arrive at Centrale or Porta Garibaldi. Drop bags at your hotel.

Afternoon: Shake off the journey with a private orientation walk to see highlights and hear local stories on the Milan Private Tour: Highlights & Hidden Gems with a Local. It’s tailored to your interests and great for first-time visitors; ask your guide for current exhibits and restaurant tips.

Before the tour, grab a light lunch: try Luini (near the Duomo) for hot panzerotti; in Brera, Princi for focaccia and salads or Obicà for mozzarella plates. Coffee and a sweet pick-me-up at Pavé (buttery croissants) or Marchesi 1824 (historic pastry house; there’s a beautiful branch inside the Galleria).

Evening: Head to the Navigli canals for aperitivo—order a Negroni Sbagliato where it was invented and you’ll fit right in with Milan’s pre-dinner ritual. For cocktails, try MAG Café (mixology with soul) or Rita & Cocktails (creative classics). Dinner nearby: Osteria del Binari (old-Milan atmosphere; ossobuco, saffron risotto), Trattoria Madonnina (comforting, unfussy Milanese dishes), or El Brellin (romantic, historic setting by the canal). Finish with gelato at Il Massimo del Gelato (dense, flavorful) or Cioccolati Italiani (chocolate-forward cones).

Day 2 — Duomo, The Last Supper, Sforza Castle, and Departure

Morning: Start early at the Duomo piazza as the city wakes. Join a small-group experience that efficiently covers both icons: Milan Duomo & The Last Supper Skip-the-Line Small Group Tour. You’ll skip queues, tour the cathedral, and see Leonardo’s mural at Santa Maria delle Grazie—time slots are limited to preserve the masterpiece, so booking ahead is key.

Breakfast options nearby: Marchesi 1824 (Galleria) for cappuccino and pistachio cream croissant, or Panificio Davide Longoni (if you’re closer to Porta Romana) for sourdough pastries. If your tour starts later, swap the order and begin with the Duomo rooftop first.

Afternoon: Walk through the Galleria Vittorio Emanuele II (peek at the mosaic bull on the floor for a local good-luck spin), then continue to La Scala and the elegant Brera quarter. Art lovers can explore the Pinacoteca di Brera (Raphael, Caravaggio, Mantegna). Otherwise, head to Sforza Castle for courtyards and the green sweep of Parco Sempione; a short climb up the Branca Tower gives city views. Quick lunch: Il Salumaio di Montenapoleone (courtyard, salumi and pasta), Trattoria Torre di Pisa (Tuscan comfort, beloved by locals), or a fast slice at Piz (soft, airy pizza with friendly service).

If time allows before you depart, add a dedicated Duomo deep dive with fast-track entry and rooftop access on the Duomo di Milano: Guided Cathedral Tour & Rooftop Access Included—the forest of marble spires and close-up gargoyles are unforgettable.

Departure: Pick up last-minute gifts—Panettone from Marchesi or amaretti from G. Cova. For airport transfers, allow: Linate ~20–30 minutes (Metro or taxi), Malpensa ~50–60 minutes (Malpensa Express), Bergamo ~60–75 minutes (coach). For European flights or trains, compare live schedules and prices on Omio (flights) and Omio (trains); for long-haul searches use Trip.com.

Local Tips, Shortcuts & Good-to-Knows

• Reservations: Book The Last Supper weeks ahead. For dinner at Trippa or Ratanà, reserve as soon as you can; walk-ins are tough.
• Dress code: Shoulders/knees covered for the Duomo and churches; bring a light scarf.
• Transit: Validate paper tickets; tap-in/tap-out on Metro gates. Classic tram no. 1 is a scenic ride past many sights.
• Shopping: Quadrilatero d’Oro for designer boutiques; Corso Como and Porta Nuova for contemporary Italian brands.
• Rain plan: Pinacoteca di Brera, Museo del Novecento, Fondazione Prada, and La Scala Museum are excellent indoor choices.

Optional Day-Trip Idea (If You Add a Day)

If you extend your stay, Lake Como is an easy classic from Milan (train to Como ~40 minutes; organized tours include boats and village time). Consider the Lake Como & Bellagio Day Trip with Private Boat Cruise for stress-free logistics and postcard views.

Where to book transport: Within Europe, compare trains and flights on Omio (trains) and Omio (flights). For non-Europe or long-haul searches, use Trip.com. Stay central with Room Mate Giulia or browse Hotels.com and VRBO.

In two days, you’ll have touched Milan’s big three—Duomo, The Last Supper, and Navigli—plus time for Brera and the castle park. If the city’s blend of art, design, and cuisine hooks you, return for a longer stay or add a Lake Como day trip next time. Buon viaggio!