Milan, once Roman Mediolanum, grew from a Lombard capital into Europe’s style engine. Its Gothic Duomo is a forest of spires, its canals recall Leonardo’s engineering, and its galleries make modern design feel inevitable. Between espresso counters and atelier windows, the city hums with history in motion.

A couple of hours north, the Swiss Alps rise into ice and light. The Bernina line curls past glaciers and sky-blue lakes, cresting the UNESCO-listed Bernina Pass before dropping into St. Moritz, a rare mix of high mountain air and high culture. In summer you’ll find wildflower meadows and lake paths; in winter, world-class skiing and clinking fondue pots.

Practical notes: Italy uses EUR; Switzerland uses CHF. Trains are punctual and scenic—and often the best way to travel. Book Da Vinci’s Last Supper well in advance, carry layers for changeable alpine weather, and note Swiss sockets (Type J). Aperitivo in Milan is a delicious ritual; in the Engadin, try capuns, pizzoccheri, and nut cake.

Milan

Milan is Italy’s capital of fashion and finance—but also of craftsmanship: marble carvers finished the Duomo over six centuries, and bakers perfected panettone long before catwalks. Neighborhoods shift from stately Brera to bohemian Navigli, with canals built to move marble for the cathedral and now lined with bars and galleries.

• Top sights: Duomo rooftop terraces, Galleria Vittorio Emanuele II, La Scala, Brera’s Pinacoteca, Sforza Castle, the Navigli canals, and the avant‑garde Porta Nuova skyline.
• Culinary highlights: saffron risotto, cotoletta, ossobuco, and the aperitivo hour—plus superb pizza, pastas, and patisserie.
• Fun fact: The “Negroni Sbagliato” was born here by happy accident—sparkling wine instead of gin.

Where to stay: Browse well-located apartments and hotels on VRBO Milan or compare top picks on Hotels.com Milan.

Getting in: Fly into MXP/LIN/BGY. For flights within Europe, search Omio flights. For long-haul, compare on Trip.com flights or Kiwi.com. Trains to Milano Centrale from other European cities: check Omio trains.

Great tours and tickets (reserve early for the Last Supper):

• Milan Duomo & The Last Supper Skip-the-Line Small Group Tour — a deep dive into two icons with expert context.

  

• Milan: Pasta and Tiramisu Small Group Cooking Class with Wine — roll fresh pasta and whisk tiramisù in a beloved local kitchen.

  

• Lake Como & Bellagio Day Trip with Private Boat Cruise — villas, mountains, and the prettiest lanes on the lake.

  

• Milan Gourmet Tour with Starry Dinner and Exclusive Tastings — an evening of refined bites and stories behind them.

  

St. Moritz (Swiss Alps)

St. Moritz sits in the high Engadin valley, a sun‑kissed cradle of winter sports and modern alpine hospitality. The light is famously crisp; the lake, a mirror for peaks; and the funiculars whisk you to panoramas that feel borrowed from postcards.

• Top experiences: ride the Bernina line over the pass, stroll Lake St. Moritz, funicular to Muottas Muragl, hikes on Corviglia or Corvatsch, spa time at Ovaverva, and day trips to Morteratsch Glacier.
• Food to try: capuns (spätzle wrapped in chard), pizzoccheri from nearby Valtellina, Bündnerfleisch, and Engadiner nusstorte.
• Winter bonus: superb skiing and an exhilarating toboggan run from Preda to Bergün.

Where to stay: See chalets and apartments on VRBO St. Moritz or hotel deals on Hotels.com St. Moritz.

Getting there from Milan: Train Milan Centrale → Tirano (about 2h30; ~€12–15), then Tirano → St. Moritz on the Bernina line (about 2h; CHF ~32–40 on regional trains; seat reservations for the panoramic Bernina Express are optional, CHF ~26–48). Search schedules and fares on Omio trains. Total travel time: ~4.5–5 hours.

Guided Bernina options (from Milan, great if you prefer an organized day):

• Swiss Alps Bernina Red Train and St.Moritz Tour from Milan — classic, scenic day out with time in St. Moritz.

  

• From Milan: St. Moritz and Panoramic Bernina Express Tour — coach plus panoramic carriage for big-window views.

  

Day 1: Arrival in Milan, canals and aperitivo

Morning: Travel day. If you land early, drop bags and take a gentle loop through the Galleria to feel Milan’s rhythm.

Afternoon: Check in near the center. Espresso and a sweet start at Pavé (buttery croissants, seasonal cakes) or Marchesi 1824 (historic patisserie). Walk Via Torino to the Navigli canals; browse vintage shops and design boutiques.

Evening: Aperitivo along Naviglio Grande—try Mag Cafè for inventive sips or Rita for balanced classics with generous snacks. Dinner options: Trippa (seasonal Milanese plates; book ahead), Ratanà (modern Lombard in a Liberty‑style building), or Osteria del Treno (classic risotti near Centrale). Nightcap at Bar Basso, birthplace of the Negroni Sbagliato.

Day 2: Duomo, Da Vinci, and Milanese flavors

Morning: Beat crowds at the Duomo. If you want expert context and guaranteed access, join the Milan Duomo & The Last Supper Skip-the-Line Small Group Tour to cover both icons efficiently.

Climb the rooftop terraces for a sea of spires and a peek at the golden Madonnina.

Afternoon: Lunch ideas: Luini for hot panzerotti, De Santis for stuffed focacce, or Latteria San Marco for homey pastas. Stroll Brera’s lanes and Pinacoteca, then swing by Sforza Castle and Parco Sempione for greenery. Coffee at Taglio or Orsonero.

Evening: Roll up your sleeves at the Pasta & Tiramisu Small Group Cooking Class with Wine for a hands-on dinner you make yourself.

Alternatively, savor an elevated tasting route on the Milan Gourmet Tour with Starry Dinner. For cocktails, try Nottingham Forest’s award‑winning list.

Day 3: Lake Como and Bellagio (full-day tour)

Reserve a full day for villas, mountains, and water. Join the Lake Como & Bellagio Day Trip with Private Boat Cruise (typically ~10 hours).

Glide past grand villas, explore Como’s cathedral quarter, and wander Bellagio’s stone stairs. Lunch picks in Bellagio: Trattoria San Giacomo (lake fish, pastas) or La Terrazza (views and risottos). Back in Milan, dine at Casa Tua Osteria (warm, Roman‑leaning) or Dry (excellent pizza and cocktails).

Day 4: To the Swiss Alps via the Bernina line; sunset in St. Moritz

Morning: Depart Milan Centrale for Tirano (~2h30; €12–15). Continue Tirano → St. Moritz on the Bernina route (~2h). For timetables and tickets, use Omio trains. Consider reserving panoramic seats on the Bernina Express for wide-angle windows (supplement applies) or ride the regular regional cars and hop on/off en route.

Afternoon: Check in and take a leisurely lap around Lake St. Moritz. Coffee and Engadin nut cake at Confiserie Hanselmann (a 19th‑century favorite) or Hauser for pastries and hot chocolate.

Evening: Dinner ideas: Chesa Veglia (rustic pizzeria and grill inside a centuries-old farmhouse), Dal Mulin (seasonal Swiss‑Italian), or Veltlinerkeller (pizzoccheri and grilled meats). Digestif at Pavarotti & Friends Wine Bar.

Day 5: Peaks and panoramas—Muottas Muragl and Corviglia

Morning: Ride the Muottas Muragl funicular for sweeping views over the Upper Engadin lakes. Walk the Panoramaweg to Alp Languard if conditions allow, or simply linger on the terrace.

Afternoon: Corviglia time: take the funicular from St. Moritz Dorf and ride higher lifts for hiking (summer) or skiing (winter). Lunch at Bergrestaurant Trutz (sunny deck, rösti and soups) or El Paradiso (legendary views; reserve in peak season).

Evening: Ease muscles at Ovaverva pool and spa. Dinner at Hotel Steffani’s Le Lapin Bleu (roasts, lake fish) or try a fondue night—perfect after a mountain day. Night stroll under crisp Engadin stars.

Day 6: Bernina Pass highlights—glacier and blue lakes

Morning: Board a regional train toward Morteratsch. Walk the well-marked glacier trail (family‑friendly, informative panels tracing glacier retreat). Coffee and cake at the Morteratsch hotel/restaurant by the station.

Afternoon: Continue up to Alp Grüm for a late lunch—expect panoramic plates with emerald Lago Palü below. If you prefer wheels, rent bikes in St. Moritz and follow the gentle Inn River path toward Bever and Pontresina (summer).

Evening: Back in St. Moritz, browse Via Serlas boutiques or the Segantini Museum for alpine light on canvas. Dinner at Chesa al Parc (classic Swiss in a pine‑paneled room) or Bobby’s Pub for a relaxed burger and local beers.

Day 7: Easy morning and departure

Morning: Brunch at Hauser’s sunlit terrace or Hanselmann. Last warm stroll along the lake or a short cable car up to Salastrains for a final panorama.

Afternoon: Depart by train. For most itineraries, St. Moritz → Chur → Zürich Airport takes ~3h45–4h30 (CHF ~60–90). If returning to Italy, St. Moritz → Tirano → Milan takes ~5.5–6.5h (mix of CHF/EUR tickets). Compare routes and book on Omio trains. For onward European flights, check Omio flights; for intercontinental options, see Trip.com or Kiwi.com.

Where to sleep each night (quick reference):

• Nights 1–3: Milan — search VRBO Milan or Hotels.com Milan.
• Nights 4–6: St. Moritz — browse VRBO St. Moritz or Hotels.com St. Moritz.

Transit recap:

• Milan → Lake Como day trip: frequent trains Milano Cadorna/Centrale → Como S. Giovanni (40–60 min; €5–7) or take the curated tour above.
• Milan → St. Moritz: ~4.5–5h via Tirano and Bernina line; book on Omio trains.
• St. Moritz → Zürich Airport: ~3h45–4h30 via Chur; or return to Milan in ~6h.

This one‑week Milan and Swiss Alps itinerary blends Italy’s art and cuisine with Switzerland’s grand scenery. From cathedral spires to glacier views, you’ll move mostly by beautiful trains—and eat wonderfully along the way. Buon viaggio, gute Reise!