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The Only Milan 2 Day Itinerary You'll Ever Need

How to spend 48 hours in Italy's hub of finance, fashion and design


Milan skyline, Italy

Lying invitingly at the foot of the Alps, Milan is Italy’s most buzzing city. Whether your poison is stock exchanges and skyscrapers (those business emails should really wait until you’re back from holiday, though), luxury shopping (credit card at the ready) or history and culture (ignore what the kids say - you can never see too many museums), this place has it all. With our Milan 2 day itinerary and a remarkable Milan home to stay in, you’re set for a wonderful trip. And here at Plum Guide, we've done all the had work for you (you're welcome), so you don't have to worry about a thing. Aren't you lucky?

Day 1: Get out into the city

Admire the view from the Duomo rooftop

Duomo Catherdral, Milan

Duomo Catherdral, Milan

No matter what time your flight gets in, the absolute first thing you have to do is head to the Duomo, Milan’s gothic centrepiece. For a panoramic view of the city, climb the 251 steps to the rooftop (or take the lift to the top if your knees are feeling creaky - no judgement, we’ve all been there), enjoy the 360 degree view and play hide and seek among the 3,500 statues.

Parakeet, Plum Guide home in Milan

Parakeet, Plum Guide home in Milan

Brush up on contemporary art

Once you’re back on solid ground, stroll to the nearby Museo del Novecento which has an intriguing collection of 20th century artworks, featuring pieces by Kandinsky, Picasso and Modigliani. It’s an unmissable stop in your two day itinerary of Milan. If any of your younger travelling companions complain about being made to look at art, bribe them with a gelato from GROM, just across the square.

Shop until you drop

Once you’ve soaked in enough historical and cultural charm to see you through at least the next few dinner parties, it’s time to hit the shops. Galleria Vittorio Emanuele II is one of the world’s oldest shopping emporiums. Built in 1867 and comprised of a four-story double arcade with mosaics, marble floors and a glass ceiling, it’s truly fabulous, darling. We strongly advise sipping an early apertivo and indulging in some people-watching as Milan’s finest swirl around you.

Peregrine, Plum Guide home in Milan

Peregrine, Plum Guide home in Milan

Take a leisurely walk before eating at a top restaurant

The artistic quarter of Brera is a picturesque neighbourhood to walk through on your way to a slap-up dinner. Pause to browse the independent boutiques and quirky stores, enjoying the evening atmosphere and buying things you'll never use back home. Then for dinner, Identità Golose, nested in the heart of the Brera district, is a gastronome’s delight. Your dining companions will definitely not love your in-depth analysis of the terroir of the ingredients. You’ll enjoy Milanese dishes with a strong Southern Italian influence. Famous chefs from Italy and beyond, with past guests including Alain Ducasse and Massimo Bottura, prepare dinner here.

Day 2: Treat yourself to a show

Enjoy The Last Supper with a full stomach

After you’ve dragged yourself out of your comfortable bed - and no, you can’t stay in the apartment all day because it’s so nice - kick off the second half of your Milan 2 day itinerary with an espresso and a morning pastry at one of Milan’s oldest cafes, Pasticceria Marchesi. Although it conveniently has three locations around the city, the service leaves much to be desired, so you’ll even get to experience that holiday classic, staring extra-hard at a waiter to get his attention. After you’ve brushed the crumbs from your trousers, head to the Chiesa di Santa Maria delle Grazie and absorb Leonardo’s genius in person.

Glass & Steel, Plum Guide home in Milan

Glass & Steel, Plum Guide home in Milan

Order a seafood meal before walking the runway

A quick taxi ride to the other side of the city will get you to Paper Moon Giardino, an elegant restaurant in a 19th century palazzo. Request a table al fresco, order a large glass of wine (you’re on holiday! Get the bottle) and feast on fish tartare, made with your choice of red shrimp, tuna or sea bass. Nearby is Milan’s fashion quarter and - wait, did Donatella Versace just walk by? We definitely think it was her - the heart of the district is the Via Monte Napoleone, home to the big Italian labels such as Valentino and Bottega Veneta.

Grab a box at the opera

This is one for all you opera lovers. The world-famous opera house Teatro all Scala shouldn’t be missed during your Milan 2 day itinerary. But if you can’t quite manage to sit through a whole performance - there’s no need to be ashamed, sometimes pizza is calling out your name - you can sneak inside and admire the gilded gold balconies and red velvet interiors as long as there isn’t a rehearsal or performance.

Synthesis, Plum Guide home in Milan

Synthesis, Plum Guide home in Milan

Try the classic veal Milanese

For a late-night dinner, you just can’t beat Antica Trattoria della Pesa. You must order the veal Milanese - it’s a classic for a reason. Located in a 19th century weigh station, you’ll be reminiscing about the cosy ambiance to your friends until they get totally sick of you.

Go out on the town

Navigli, Milan, Italy

Navigli, Milan, Italy

If you’re not yet ready to call it a night (you daredevil, you) then walk to the bustling nightlife district of Navigli to enjoy a nightcap or two...or three in one of the brightly lit bars next to the canal. As you stroll back to your spacious apartment in the heart of Milan, you’ll dream about moving to Italy, before realising it just wouldn’t be worth it if you couldn’t live in the Plum home you stayed in.

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