Welcome to Milan, Italy’s forward-looking engine of fashion, finance, and design. Beneath its sleek surface lies a city layered with Roman roots, Renaissance genius, and modern architectural swagger. Think Gothic spires at the Duomo di Milano, Leonardo’s Last Supper, and glassy skyscrapers framing the vertical forests of Porta Nuova.

Fun fact: Milan pioneered the ritual of aperitivo—order a drink at the right spot and a spread of snacks appears. It’s also home to La Scala, one of the world’s most storied opera houses, and to two legendary soccer clubs that share the colossal San Siro stadium. Day trips to Lake Como, Bellagio, and even the Swiss Alps are effortless from here.

Practical notes: Reserve Last Supper tickets well in advance (they sell out weeks ahead). Dress modestly for churches, including the Duomo. Urban transport is excellent; cashless payments are widely accepted. Food highlights include saffron risotto (risotto alla milanese), ossobuco, cotoletta, panzerotti, and expertly pulled espresso.

Milan

Milan is Italy’s fashion capital and an art lover’s dream, where haute couture windows face medieval castles and cutting-edge galleries. Neighborhoods each have a vibe: Brera is artistic and walkable; Navigli is canal-side nightlife; Porta Nuova is all glass and gardens; Magenta hides Renaissance treasures.

• Top sights: Duomo di Milano (cathedral and rooftop), Galleria Vittorio Emanuele II, La Scala, Sforza Castle & Parco Sempione, Brera district & Pinacoteca, Santa Maria delle Grazie (Last Supper), Porta Nuova & Bosco Verticale, Navigli Canals.
• Dining & drinks: Try risotto at Ratanà, aperitivo at Camparino or Bar Basso (home of the Negroni Sbagliato), pizza al trancio at Spontini, panzerotti at Luini, and gelato at La Romana.
• Fun facts: Milan’s Duomo took nearly six centuries to complete; Leonardo worked here for almost 20 years; and Milan Fashion Week sets global trends twice a year.

Where to stay (browse and book):

• Browse apartments on VRBO Milan or hotels on Hotels.com Milan.
• Hotel Principe di Savoia (classic grandeur, spa) — book here.
• Room Mate Giulia (design-forward steps from the Duomo) — book here.
• UNAHOTELS Cusani Milano (between Sforza Castle and Brera) — book here.
• Ostello Bello (top-rated social stay near Duomo) — book here.

How to get to Milan:

• Flights within Europe: compare on Omio (flights in Europe). From Paris/London/Madrid you’ll find many daily nonstops to MXP (Malpensa) and LIN (Linate).
• Flights from outside Europe: search on Kiwi.com or Trip.com (flights).
• Trains in Europe: book high-speed options on Omio (trains) — Rome→Milan ~2h55 (€35–95), Venice→Milan ~2h25 (€25–60), Paris→Milan ~6h45 (€29–139).
• Airport to city: Malpensa Express to Milano Cadorna/Centrale ~50–60 min (~€13); Linate M4 metro to San Babila ~15 min; Bergamo (Orio al Serio) coach to Centrale ~50–60 min (~€10).

Day 1: Arrival, Duomo Quarter, and Aperitivo

Afternoon: Arrive and check in. Stretch your legs around Piazza del Duomo to feel Milan’s pulse. Step into the Galleria Vittorio Emanuele II to admire its 19th‑century glass vaults and mosaic floors; spin on the bull mosaic for good luck, a local tradition.

Evening: Toast your first night with an aperitivo. Great picks: Camparino in Galleria (legendary bitter cocktails), Terrazza Aperol (Duomo views), or Bar Basso (home of the Negroni Sbagliato). For dinner, consider Trattoria Milanese (old-school ossobuco and risotto), Risoelatte (retro 1960s décor, comfort Milanese), or Pizzium (regional pizzas, playful toppings). Finish with gelato at Cioccolati Italiani near the Duomo.

Day 2: Duomo, The Last Supper, Brera, and a Hands-On Cooking Class

Morning: Fuel up at Marchesi 1824 (polished pastries) or Pavé (artisan croissants and cappuccino). Then join this small-group tour—ideal because it secures two hot tickets in one go and saves time queueing:

Milan Duomo & The Last Supper Skip-the-Line Small Group Tour

Expect a guided visit inside the cathedral, time on the square, and reserved entry to Leonardo’s mural at Santa Maria delle Grazie. Tip: shoulders and knees covered for church entry; photography rules vary inside the Last Supper refectory.

Afternoon: Grab a quick Milan classic: panzerotti at Luini (soft fried dough stuffed with tomato and mozzarella), a toasted panino at De Santis, or a slab of pizza al trancio at Spontini. Wander Brera’s cobbles: Pinacoteca di Brera (Raphael, Mantegna), the tiny Orto Botanico garden, and stylish boutiques. Espresso stop: Orsonero Coffee or Cafezal Roastery.

Evening: Learn to cook like a local in a convivial, small-group kitchen—perfect for a tasty souvenir you can replicate at home.

Gnocchi, Pasta, Tiramisù and Wine Class

Nightcap options: Nottingham Forest (inventive cocktails), Mag Café (Navigli), or Rita (balanced, modern drinks). If you’re hungry again, late bites at Osteria del Binari near the canals are reliable.

Day 3: Day Trip to Lake Como and Bellagio (Boat Cruise Included)

Trade urban energy for alpine-lake elegance on a full-day guided excursion. Expect Como’s historic center, a scenic boat ride, and postcard views in Bellagio—backed by snow-dusted peaks in shoulder seasons and lush green in summer.

Lake Como & Bellagio Day Trip with Private Boat Cruise

Why we like this: it bundles logistics (coach + cruise) so you maximize time on the water and in lakeside towns. Bring layers, comfortable shoes, and a camera. On return, dine back in Milan—try Ratanà (refined Lombard cuisine in Porta Nuova), Nerino Dieci (beloved bistro), or Osteria Alla Concorrenza (natural wine and hearty plates).

Day 4: Modern Milan, San Siro, and Navigli by Night

Morning: Breakfast at Pavé or Princi, then head to Porta Nuova’s Biblioteca degli Alberi park to admire the Bosco Verticale (tree-clad towers). Walk Corso Como and pop into 10 Corso Como’s concept store if you love fashion and photography.

Afternoon: Soccer fans, this one’s essential—tour one of Europe’s most iconic stadiums, home to AC Milan and Inter. You’ll access dressing rooms, the tunnel, and the museum.

Milan: Official San Siro Stadium and Museum Tour

For lunch beforehand, consider Eataly Smeraldo (regional counters under one roof), Casa R Ameni (seasonal modern plates), or Miscusi (handmade pasta, quick and tasty).

Evening: Aim for Navigli at golden hour. Stroll the canals, browse vintage shops, then settle for aperitivo at Mag Café, Rita, or Officina 12 (courtyard charm). Dinner ideas: Trippa (celebrated trattoria—reserve), Al Pont de Ferr (creative techniques along the canal), or Osteria del Binari (classic Milanese in a garden setting). For a skyline toast, book Ceresio 7 (rooftop pool and views).

Day 5: Fondazione Prada, Design Vibes, and Last Shopping

Morning: Coffee at Bar Luce (Wes Anderson’s pastel daydream) inside Fondazione Prada, then tour the museum’s contemporary exhibitions. Alternatively, if you’re art-meets-history inclined, the Monumental Cemetery is an open-air sculpture gallery that’s quiet and profound.

Afternoon: Lunch in Brera at N’Ombra de Vin (wine cellar with Venetian flair) or in Chinatown (Via Paolo Sarpi) at Ravioleria Sarpi (handmade dumplings) if you’re craving variety. Wrap up with fashion hunting in the Quadrilatero d’Oro (Via Montenapoleone, Via della Spiga) or pick up edible souvenirs (aged cheese, risotto rice, gianduja) at Eataly Smeraldo. Depart in the afternoon—M4 to Linate, Malpensa Express to MXP, or coach to Bergamo.

Evening (if you have extra time): Another cathedral angle: consider a dedicated rooftop visit with a guide for the flying buttresses and marble close-ups:

Duomo di Milano: Guided Cathedral Tour & Rooftop Access Included

Optional add-ons for extra days: If you can stretch your stay, consider a scenic rail adventure into the Alps with a UNESCO-listed route and dramatic passes (full-day):

• Swiss Alps Bernina Red Train and St.Moritz Tour from Milan

Local tips: Many restaurants are closed on Sundays/Mondays—check hours and reserve for hot spots. Taxis are regulated; rideshares operate, but the metro is often faster. For the Last Supper, tickets can vanish 3–6 weeks ahead—book as early as you can.

Getting around: Milan’s metro and trams are efficient; a day pass pays off if you’re sightseeing widely. For regional trains or buses, compare on Omio (trains) and Omio (buses).

Quick accommodation recap: Explore VRBO Milan or Hotels.com Milan; favorites include Hotel Principe di Savoia, Room Mate Giulia, UNAHOTELS Cusani Milano, and Ostello Bello.

In five days you’ll taste Milan’s greatest hits—Duomo pinnacles, Leonardo’s fresco, stylish neighborhoods, and a blue-lake escape to Como—while savoring risotto, aperitivi, and late-evening strolls along the canals. This plan balances icons and insider haunts so you leave with both epic photos and authentic memories.