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Weekend in Milan: Day One Itinerary

During a weekend in Milan you get a sense of the northern Italian city’s vibe, an exciting place for fashion, style and industry. On day one we found ourselves on the most fashionable street in the world, a sky high cathedral and in the heart of a buzzing nightlife district.

Weekend in Milan

Milan. I think fashion capital of the world.  There’s more than high fashion. Look deeper and it’s a true metropolis. It is where Italy’s stock exchange is located, where industries are manned and the global capital of design.

Day One Itinerary in Milan

Here’s what we saw during day one of our quick city break weekend in Milan, all on foot or by metro.

The Duomo

This is the city’s most famous landmark which is just referred to as ‘The Duomo.’  I understood right away why it is deserving of the mononym. It is one of the grandest and largest Gothic cathedrals in the world.

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As a result of 400 years of work, a spectacular forest of stone pinnacles rise above more than 3,500 intricately carved statues.  The Duomo has something literally above the rest when compared to other European cathedrals – its accessible rooftop.


Galleria Vittorio Emanuele and Teatro alla Scala

The Duomo’s square sits next to another city landmark hailing from another era called the Galleria Vittorio Emanuele.  We walked through the glamorous glass-vaulted shopping gallery for a look. Be sure to check out the steel and glass dome hovering high above you.


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Upon leaving we found a little Piazza della Scala and across it the world’s most renowned opera houses, Teatro alla Scala. For the past 200 years, the finest singers have performed there.

Via Montenapoleone

While we headed from the Teatro alla Scala to check out the famous shopping street Via Montenapoleone, I had an opportunity to observe how a good number of Milanese get around town.  They scoot by on Vespas and whiz along on mostly old-fashioned bicycles, many of them complete with a wicker basket in front and a baby seat strapped on back. Love.


Soon enough, there it was — Via Montenapoleone.

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The street is the main artery of Milan’s Quadrilatero d’Oro which translates to Golden Rectangle. This part of town houses the head boutiques for Prada, Armani, Missoni and Versace.

The choice modes of transportation were flashy cars like Lamborghinis and Maseratis.  Their drivers cruised by ever so slowly and parked in the right places to be seen.   Also on display? Long-legged models and Italian women with a passion for high fashion.


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We rested our shopping feet at Cova (Via Montenapoleone 8) which offered fine coffee, pastries and small lunches. This café has called the boutique street home since 1817.

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Castello Sforzesco and Parco Sempione

After we had our first encounter with Milan’s fashion world we backtracked towards the Montenapoleone metro station to Via Cusani.  In ten minutes, the imposing gates of Castello Sforzesco were in view. A refreshingly active water fountain graced the entrance to this massive brick bastion which was once a fortress in 1451. It now houses numerous art collections from around the world.  A must see.


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We headed across the castle’s grounds and found the Parco Sempione, Milan’s largest public park.  Clean, expansive and well-kept, it’s a haven for Italians to relax with family and friends for bike riding, picnicking and sunbathing.

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As you enter notice the city’s triumph arch, the Arco della Pace, as it sits grandly in the distance beyond layers of rolling green and colorful gardens.


That night we headed to Navigli which is a neighborhood built on a 30-mile canal linking the city to Lake Maggiore.

It’s a lively artsy kind of neighborhood lined with trendy flats and mom and pop shops. It’s also a hotspot for nightlife.  Restaurants, clubs and bars in this district attract locals who spill out into the streets with a drink in hand and with plenty of good company.

We enjoyed the cuisine at Bella Riva and also another night at El Brellin next to the canal.

Of course, we had to go for gelato after every meal.

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Have you been to Milano? What were your favorite sights?




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