Before we get started, I’d like to point out a few critical points for those planning on visiting Milan in the future:

  1. One weekend is sufficient to see the whole of Milan
  2. Very much unlike Rome, Athens and Prague, the historical monuments and sights are limited
  3. Whatever you do, try to stay in the city center and explore from there. 
  4. Milan is a very expensive city in terms of dining, shopping and nightlife. It is almost on par with Copenhagen
  5. Pay attention to your attire – you might feel really out of place in this fashion capital
  6. You will have no problems getting around. Public transport is one of the most efficient in Europe. The signs and directions at each station make it extremely easy to find the right train.
  7. Uber works in Milan but of course the price range is higher.

That out of the way, let’s get this party started! Here’s how I spent 5 days solo in Milan.

I hate flying. A lot. But I am somewhat excited this time because I will finally get my Italian cousins off my case. I’ve got grief for never having been to Italy before.

My preflight ritual is a mimosa, maybe ten. For some reason it helps me relax before take off.

I’m flying out of Nuremberg so I head to the Albert Dürrer Airport lounge – I have access to lounges in over 900 airports around the planet through my American Express platinum card. This is a must-have card for frequent travelers. The travel benefits are unreal.

See if you qualify here through this personal referral link: http://refer.amex.us/OLAoLMMK8a?XLINK=MYCP

Two mimosas later, I am lucky to make my flight. I was pretty much the last to get on the plane. One of the hostesses recognizes me and I wonder how because I’m flying Ryanair for the first time. I must have met her during my party days around Europe.

Before we get into this, you can have a look at my 4 minute video, a summary of my time in Milan here: https://www.youtube.com/watch?v=dDgbHVYyPIY&t=10s

Let’s get down to business then, shall we?


A view of Milan from Torre Blanco. Photo by The Wanderer

DAY 1

08:45 – Honestly, I couldn’t make up my mind on how to feel about the city. I usually get an instant ,unique vibe from every city I visit but this looks like it might take a few days to get an impression. However, my  impression of the people was different. People paid attention to their outfits and looked like they were auditioning for GQ magazine.

Anyway, I landed in Bergamo Airport, approximately an hour away from central Milan. My airport shuttle final stops is at the sketchy looking parking lot of Milano Centrale Station and from there  I took a cab to my hotel.

10:12 – I’m staying at the Leonardo City Center Hotel which is pretty decent. I was pleased with my choice of hotel – huge room, huge bed, a welcome note, complimentary bottle of wine, the works. The bed is calling my name but I am unwilling to go gentle into that good night.

I might as well walk around the city. As a travel blogger new to the game, I can’t wait to start taking photos and documenting every single thing I find interesting. So I strap myself with the tools of the trade – camera, GoPro and my laptop.

10:30 – A brief conversation with the hotel front desk and I realize there is nothing central about its location. The city center is a 30 minute walk away. Talk about false marketing. I am absolutely devastated. Normally I’d try to stay in the center everywhere I go and explore from there. I have no sense of direction and get lost very often. Getting lost in a new city ain’t such a bad thing anyway but it’s me we are talking about here.

“The bed is calling my name but I am unwilling to go gentle into that good night.”

10:45 – 11:40 – So, I decided to walk to Parco Sempione, Milan’s main recreational park. I had read an article the day before mentioning a very high point in the park called Terra Branco and since I live for skylines and views, I decided to go take photos.

6 Euro and 25 minutes later, I am on the elevator to the top of one of the city’s highest points. I can tell you the 360 view is absolutely stunning. Too bad the session only lasted a few minutes.

12:00 – With my photo session over, I walked through the park looking for a place to have a drink. Every hour is drink o’clock for me when i’m on vacation.

Around 12:25 – I stumble upon a bar/lounge/restaurant called Bar Bianco inside the park and as I write this, i’m sipping on a world class Mojito. A few sips into my drink, I realize my cigarettes are in my hotel. Bloody hell! I asked a server where I could get cigarettes and he offered to ask his old man on my behalf. 

We get to talking and the guy’s dad owns the bar! Maybe there’d be future friends and family discounts for me.

I spent about two hours drinking cocktails, working on this blog post and chatting with Loris and William Marchese, the owners of Bar Bianco.

I took this opportunity to ask for the best places to party for a solo traveler. Guess who forgot to write down the suggestions? Blame it on the cocktails. I am just going to have to go with the flow. Time to head back to my hotel.


Bar Bianco, Parco Sempione, Milan. Photo by The Wanderer

18:30 – I head downtown for dinner and cocktails. Finding the closest tram station from my hotel was quite easy. I ate at a Chinese restaurant and proceeded to look for a bar.

Surprisingly, I couldn’t find a proper bar after about an hour of walking around. I ended up at Il Mercato, one of Milan’s most famous restaurants/bars.

Three or four cocktails later I am ready to get my party on. I had a short conversation with one of the servers and he recommended Corso Como, one of Milan’s main party districts. The server writes down his recommendations and I am on my way. Its going to be one of those nights I live for…the ones I forget.

I wish I remember the names of all he bars I went to, but how could I forget meeting an awesome middle-aged bartender/owner named Uncle at Flamingo Bar. Her strong cocktails are to blame for my amnesia.

My night ended at Tocqueville 13 nightclub. The bouncer informs me that it is only VIP entrance available and I must pay at least 300 EUR for a bottle. Lucky for me, one of the guys I met earlier comes outside for a smoke and tells the bouncer we are together. That’s the last I remember of that night. 

Day 2

14:32 – I woke up in my hotel room not knowing how I got back. I must have been drinking some top quality stuff because I had absolutely no headache. However, I was devastatingly dehydrated and drank every single nonalcoholic drink from my mini bar. My plan for the day was a tour of Duomo di Milano. I had purchased a skip-the-line pass the previous week through GetyourGuide. Time to shower.

15:30 – I arrive at the city center and walk to the Duomo. The only word I can use to qualify it is stunning. I stood among the thousands of people in front of the church just taking it all in. Not only was the structure fascinating but quite imposing as well.


Duomo di Milano. Photo by The Wanderer

“I stood among thousands of people in front of the church just taking it all in”

Around 16:00 – I make my way into the church and its interior is absolutely magnificent. You can tell that a lot of wealth and time was put into its design. This isn’t surprising at all; it took nearly six centuries to complete its construction. 


Inside Duomo di Milano. Photo by The Wanderer.

About fifteen minutes later, I figured it was time to go to the top. A million flights of stairs and a heart attack scare later, I am at the top of one of Europe’s most iconic cathedrals. No surprise there. I haven’t gone running in two months. At a particular corner of the roof, there’s an absolutely magnificent view of Milan. I live for views like this. Lucky for me the rooftop isn’t crowded so I am able to stay for a long time and just enjoy the view


A view of Milan from the Duomo rooftop. Photo by The Wanderer.

“A million flights of stairs and a heart attack scare later, I am at the top of one of Europe’s most iconic cathedrals.”

A few hours later, I head back to my hotel to try to rest because surely I was going out again. I ended up in Corso Como again and had a great time but I didn’t drink as many cocktails. I needed to stay sober to try to charm the ladies. And to my greatest surprise, I found a shop for legal marijuana. My friends from Colorado, California and Amsterdam would be very disappointed though. The legal THC content in Italy is only 0.5%.

DAY 3

I didn’t really have anything planned for this day. I headed to Parco Sempione and relaxed for a few hours. Afterwards I walked through Chinatown, where my ‘city center’ hotel was located.

At about 16:00 I was back in my hotel watching movies on my laptop. I needed to recover from two days of partying. Sometimes I forget that I am not 21 anymore. So I ordered a Burger and Fries via Uber Eats, had it delivered to my hotel and spent the rest of the night indoors.

I have the San Siro to look forward to in the morning.

Day 4


Stadio San Siro/Giuseppe Meazza, Milan. Photo by The Wanderer. 

The day I had been waiting for. I am going to Stadio San Siro, one of the most famous football stadiums in the world. I was in and out of the shower in 7 minutes. My record is 3 minutes from basic combat training.

One of the things I appreciate most about the city of Milan is its metro system. It is highly efficient

One of the things I appreciate most about the city of Milan is its metro system. It is highly efficient, always on time and most critical for me is the fact that I didn’t need to ask for help to find my way around. Those that have been or lived in Germany will appreciate this.

Holy shit! I am going to the San Siro. I’m so excited that I leave my hotel way too early. I ended up waiting for about two hours for the tour to commence. No complaints from me especially because I am first in line.

As I walked through the halls, I could feel the history pulsating through its walls. I grew up adoring Milan legendary captain Paolo Maldini so I made it a point to seat in his chair in the Milan dressing room (AC Milan and Inter Milan share the stadium). Despite not a footballer, the feeling when I walked out onto that pitch was absolutely incredible. I was covered in goosebumps…insane!

Unfortunately, the museum was closed for reconstruction and was relocated to a different part of the city. I decided to check out the Milan Castle instead. I heard there are loads of cafés around the castle. Looks like i’ll be day drinking for sure. I’m on holiday anyway. 


Entrance to Sforzesco Castle, Milan. Photo by The Wanderer

I wasn’t particularly blown away by the Milan Castle. I’ve definitely been to more impressive ones. Not to say it wasn’t worth visiting either way. I didn’t spend a lot of time there and took a few photos and headed for a cafe to do some writing and of course, drinking.

A few beers and two hours of working later, I did the twenty minute walk to the city center to eat my first Milanese pizza. I had the seafood pizza from Marino Restaurant.

I wasn’t particularly blown away by the Milan Castle. I’ve definitely been to more breathtaking ones.

Later that night, I was in Corso Como again but this time at Loolapaloosa Club, where I was refused entry two days earlier.

A few minutes after I got my first drink, I headed outside for a smoke and that’s when I met Valentina Vergani, an investigative journalist with tours in some of dangerous places around the world.

She’s extremely beautiful, charming, intense and in all her feistiness you can see she loves what she does.

I spent the entire night talking and dancing with her and find out she had recently just moved back home after six years living in different parts of the world. She literally begs to interview me the next day about blog which she ended up cancelling. How dare you lady!

Day 5

My last day in Milan. At this point I am a little excited to be going back home. I planned my trip to be back in time for the release of the video game The Division 2.

It took a lot of time trying to find an activity to engage in because I had seen Milan’s major sights. So I headed to the city and walked around for a couple hours.

I had a cocktail at different bars and made a few new friends that I am positive I will never see again. Of course I headed back to the center to see the Duomo one last time and like the first time, I was blown away by its magnificence.

In Conclusion…

To be completely honest, after day 3 in Milan, I was starting to get quite bored. I could have seen all the sights in one weekend. It really doesn’t offer much in terms of tourism.

Despite all these, Milan is definitely worth visiting. I think 5 days was more than enough time there especially when I had two days where I had to be creative with my activities because I had seen it all. So ideally, one weekend is sufficient to see the entire city.

If Milan end’s up on your bucket list, you should know that it is quite an expensive city in comparison to places like Munich, Brussels, Budapest and Dubrovnik.

Don’t forget to make a local connection. It is one of the reasons why we wander.

Cheers.