Solo Trip to Milano: Summer 23
- Millie Bailey
- Nov 24, 2023
- 12 min read
Wednesday 5th July
On this day, I travelled from my home, Yorkshire to Milan via a couple of trains and an aeroplane. The excitement leading up to this little adventure by myself was all there without a single fear or doubt in my mind.
Travelling around and knowing my whereabouts added to the company of myself are two activities which we’re finally coming together as a first-time experience.
I am usually the member of the girl of the group who vigorously completes the research of a destination and pitches it to the group with an itinerary, even scheduled ‘impulsiveness’!
Therefore, organising and thinking for a group of us seemed more of a responsibility and task than looking after little old me!
I love my own company and doing things for myself. I often have ‘Millie days’ where I do things that I gain great pleasure from and the time to be with me with my own thoughts and desires… which can sometimes turn out to be expensive if the Millie day turns into a shopping spree!
With being a very sociable person through conversing with my clients and being a member of a busy tight-knit friendship group, a zoning out period is most definitely needed to achieve a good balance.
Of course, by writing this I am making it sound like nobody has ever travelled alone before… but you really have to romanticise the experience to fully immerse myself, knowing I can look back and appreciate it all.
Following my 3 days in Milan, my younger sister Meg, 19, followed my same route to the airport also solo with the added experience of public transport strikes! The arrival of Meg marked the start of our 2-week Italian tour as we were to move onto Lake Como the following morning.
The full route for the trip follows as, Milan, Lake Como, Venice, Florence, Tuscany, Rome and Puglia. All of which will be touched upon in the following journals, I am just setting the scene of 2 sisters on their travels and trying to live the Dolce Vita with a 36-litre Osprey on their back in 39-degree heat.
Back to the solo trip details after the contextual interlude above.
My backpack and I travelled via train Featherstone to Leeds, which I must mention is where I bumped into my friends and their 1-week-old baby on their first trip to town as a family on their own new adventure as mum and dad! Which was a great start to my journey as it all started to feel real. As we parted ways, stepping off the train they headed for lunch in town whilst I ventured to WHSmith’s to grab some books, Dolly Alderton was the author of the trip who inspired me to start writing about some of my experiences.
After this detour, I boarded my train to Manchester airport with a M&S yoghurt granola pot and my two books. After this short journey, I was straight through security with no issues and sat with a free Costa Coffee from my loyalty card in Terminal 3. The flight was delayed an hour before the gate was announced so I sat and did a little research of the places on my radar to hit in Milan in the morning.
Boarding the Ryanair flight, I got sat in between 2 ladies also travelling alone. Sharon and I, the lady to my left, grew to know each other on an intense level with the flight being delayed another hour before take-off. I had planned to listen to a couple of podcasts during the flight, but this conversation was worth my full attention on a Wednesday evening at 9pm.
Sharon was flying to Milan to stay at her daughter’s place in Lake Como. This was the first common ground of ours as she was giving me recommendations, which all sounded incredible. but not even possible to fit into my 24 hours in the area! I was very naive to think that Lake Como was just a lake that you would visit as a day trip from Milan (to potentially scout out a future wedding venue I always thought of… with no engagement ring or boyfriend at that). We got onto talking about Abbie, Sharon’s daughter who worked for Kappa living in Como and had been for several years, the excited tone and honourable comments Sharon made about Abbie showed the abundance of owe she had for her daughter. This shone through as she showed me some of her work and achievements not only did, I take great interest in Abbie her daughter was on her creative career path which I am striving towards fulfilling. But I also loved listening to the ins and outs of their relationship and life as it reminded me of the relationship, I have with my mum.
My mum is the first person I tell my good news to, anything exciting on the horizon, anything to aim towards or keep in mind. Mainly career-wise but most definitely personal life matters too! My mum gets as ambitious as I do, and always calls me Millie Bailey, not Millie, the name she gave me was never ‘Mil’ as many of my friends and other family members would call me. I am confident in everything I do and I know my mum is always a step behind or sometimes more often than not, a step in front. She supports me in every day and always shares my experiences and successes with their friends and colleagues, she is so proud, and I sometimes forget this when I am busy and caught up in it all!
The further my and Sharon’s conversation got I noticed many similarities close to home. Not to forget that her favourite meal ever was poached eggs, not on any old toast but sourdough!! With lots of salt and pepper… my go-to dish that I cannot live without! Simple but effective. And if you know me well then you will know how many chilli flakes, I suffocate my poor eggs with, only of which my closest know and now Sharon was in that little circle too within a matter of a few hours, we just clicked! She doesn’t live far from me and was telling me about a bakery I must visit to try the array of different sourdoughs they bake fresh on a Friday morning. After a flight full of recipe sharing, dinner party hosting setups, interior design, career plans, relationships, cats, sunglasses, podcasts, and wine we landed in Milan around 11pm. Sharon and I exchanged numbers and said our goodbyes, we kept in touch the following day as I visited a few places in Milan she recommended in exchange for an image of hers and Abbie’s lunch they had made in Como.
I arrived at my Airbnb around 1am and I was most definitely ready to retire after a shower. I face-timed my mum, dad, and Meg at home to let them know that I was safe featuring an apartment tour, and then straight to sleep.
Thursday 6th July.
6AM. My eyes opened. My brain was very alert meaning there was no turning over for an extra hour. I laid in bed for a while as this is something I rarely treat myself to a home, having a scroll to see where was first to hit a bit later as I was a little commute from the centre and early morning is not in the Italian Dolce Vita.
It seemed that a coffee shop would be the smartest as it was forecast to rain between 10 and 11am. So, I headed to a cafe named Biffi where I sat inside watching the rain pour outside, with my book in hand and an apricot pastry to accompany my caffè latte. Which I quite proudly ordered in Italian, channelling the main character.
As the rain stopped, I saw the opportunity to have a brisk walk to the Armani Silos Museum. As a Fashion Degree holder, this was an exciting visit, but I didn’t expect to be as overwhelmed as I was. I walked in through the large glass doors scanned my ticket I bought online and made my way around the first-floor exhibition. I made my way to the second floor full of the accessories archive thinking wow how handy it would be to have all these in your closet (apologies for the American term however closet sounds way better than wardrobe for this luxury fashion conversation). As I reached the third floor, it hit me. This was the first time I had entered a museum and felt something. I’m not sure if it was the mood-felt lighting, the silhouettes, the glistening jewels, or the material, but a flood of emotion filled my eyes. This is where I had a little bit of a full-circle moment. Armani the designer himself had no hold over me prior to this visit, however, stood in front of these garments it reminded me of little Millie years when me and my best friend Kate designed and sketched dresses, the craziest and most colourful patterns splurged onto a page in the shape of a dress, jumpsuit or co-ord. Our imagination was wild. Every area was covered from the jewellery and accessories down to the limited-edition nail polish collaboration for the new season. No page was left unturned with an immense attention to detail, to this day I still discover this art folder when I have my seasonal clear out always taking time to remember that we always dreamt of this being real.
Now standing in this museum, in Milan THE fashion capital, on my own, with all this in mind, I think back to how if little Millie were to bump into present Millie, then she would think I want to be like her when I’m older. I couldn’t quite believe I was standing there, and it wasn’t a daydream, it was real!
I FaceTimed my mum the moment I came out of the museum and told her the HQ was next to it, telling her I was dying to go in and introduce myself as Millie Bailey. After saying this out loud I remembered I hadn’t quite learnt as much Italian as I had liked to have a memorable exchange of conversation and my mum quite kindly reminded me that not everything must be a career opportunity and to enjoy myself and the day ahead as I had lots to see and experience in a short space of time.
I now know where Armani is and I may return in the future but that was a moment in my life that I will never forget, purely down to the about of deep breaths I took as I paced around the floors of the museum.
Then it was time for some shopping and an aperitif by the canal. A glass of Sauvignon Blanc which Sharon had recommended served with 4 snacks all of which were consumed, my favourite nocellara olives, salted popcorn, salted hand-cooked crisps and some very dry circular breadsticks which I grew to like towards the end of my 2 weeks in Italy. I sat by the canal with my book resting my feet for a while and made friends with a pigeon who seemed way more interested in my nibbles than a conversation, maybe it was just the language barrier.
As it approached later afternoon, I had a stroll around the streets of Milan on my way to Leonardo’s Vineyard. I hopped into Humana Vintage and found an amazing pair of black Italian leather brogue-style slip-ons with a small heel. I had been manifesting that I would stumble across something similar to these along my trip and didn’t expect to find them on my first day, luckily, I had a little bit of breathing room for these in my bag pack so I can now call them mine!
I bought my ticket for the Vineyard and entered. By this time the sun was beaming down in the courtyard creating amazing lighting and shadows to walk around the grounds. This account vineyard was a beautiful afternoon treat to keep me away from the shops as well as taking in the architecture and interior designs belonging to the eclectic genius himself. Aromas of cedar, lemon, rural and lawn views ran through the grounds which complemented the decorative rooms giving a sense of homeliness to my solo venture.
After this historic vineyard visit, I built up a thirst of my own… however this time it was for my first Italian Aperol Spritz. I returned back to Naviglio Grande where I visited earlier that day as I had spotted a few boards advertising a 5pm ‘Happy Hour’. A few Aperol’s down I then asked the bartender for food recommendations on the canal as the hustle and bustle was on the rise at this point. L’altro Luca e Andrea was the restaurant of choice, where I decided to go for the Paccheri with buffalo mozzarella and cherry tomatoes, Bellissimo! This mountain of Italian stooge was definitely needed to stack up some of the alcohol intake.

Now that the belly was laying nice and heavy, it was time to head back to my Airbnb as by that point, as you can probably imagine my Birkenstocks were ready to withdraw. When I checked my maps for the navigation home it came up with a 1hr 45 min walk, one I was not prepared to do. After dedicating half an hour of a walk to my journey home, I stumbled across some electric bikes. SOLD. I then continued my ride back via a shopping centre where the closest drop-off point was. Picking up a refreshing scoop of lemon sorbet in a tub which entertained my 7-minute walk back to the front door of my apartment.
As the key turned my evening drew to a close I was well and truly ready to hit the hay. Ending the day the same way as it started with a fresh shower, the towel wrap was secure and the face mask went on. After 25k steps, the feet went up and a tootle to bed soon followed.
Friday 7th July.
Another morning in the city of Milan, another day to myself before Meg arrived. And to be honest, I felt like I did it all in that one day, so more of the same I thought. However, today would be slightly different as the weather was weathering! Milan hit 39 degrees on this particular day.
First on the agenda was styling the new brogues that I had bought the day before. For anyone interested in the final attire, I went for a black cami with a black mini linen skirt accessorised with a black headband and a burgundy shoulder bag backed with the daily essentials. (Actually thinking back I tell a lie, a tote bag actually made an appearance as my mini bag didn’t quite fit my book and flip flops may my brogues should rub).
On the hunt for a coffee to fuel my day, I came across the stunning Fioraio Bianchi Caffè. Where I took myself outside to immerse in the midmorning ambience on the streets of Milano. At this point I had realised I had not paid a visit to the Galleria Vittorio Emanuele II, Italy’s oldest active shopping gallery, meaning that this was my next stop. On route to this major landmark, I stopped at the Teatro alla Scala which was showing the finale viewing the Romeo and Juliet ballet that night (in hindsight I wish I would’ve seen but there’s an excuse to make a return).
The Arcade was packed with an array of mankind, there for several reasons. Some came to spin on The Legend of the Milan Bull, some came to capture their wedding day and I came to have a good old people watch and a nip into Mont Blanc. As a graduation present, my mum insisted that she wanted to gift me a Mont Blanc pen which was a whole new world to me, but where better to shop writing instruments than in Milano. I had a browse at the exceptional craftsmanship of these pens and tried a few out for function and flow which I didn’t expect for this particular Friday morning. A sensible decision was made not to purchase as I didn’t fancy trusting myself with a luxury inscribe squeezed into a backpack whilst travelling around Northern Italy for 2 weeks.
When my luxury window shopping came to a halt, the thirst from the blazing heat needed to be quenched. I found a charming courtyard with a restaurant bar named LùBar with outside tables, ideal for a little lunch. Out came the ‘Dear Dolly: Collected Wisdom’ where I resumed reading much-chronicled adventures which was helping me navigate my own thoughts and life over an Aperol Spritz and a hearty bowl of busiate pasta with pesto, almonds and confit tomatoes. Notation: my second bowl of pasta of the trip which didn’t disappoint. Opposite LùBar, was a blanket of greenery, a park named Giardini di Villa Reale, where I placed myself for the rest of my afternoon. It was essential to be sat shaded as the heat was just calling for an accidental fall into the water fountain. After lifting my head out of Alderton’s words I reached a large pond where I discovered the cutest baby turtles which occupied me for longer than they should’ve. I felt at complete peace.
Following this excursion I took myself back to my Airbnb, then headed back out about 8pm CET. The plan of attack was to take myself for Friday night rooftop drinks and then meet Meg who was following the same route as I did 2 days prior. I reached the Terrazzo Aperol as I convinced myself that this would be a place to be for the typical signature aperitif. I was very wrong. Without slandering the bar I was not impressed and it did not satisfy my Dolce Vita fantasy. I then swiftly took myself to the Campari Bar where I was much more fulfilled. At first, I felt rather out of place as a lonesome, but I sat at the bar where I got recommended a drink to suit my preferred palate whilst taking in its stunning liberty furnishings and innovative decor with packing views of the Duomo. As I positioned myself whilst I enjoyed my own company with a chilled Campari-infused beverage, I received a message that Meg had landed! On my travels into the centre, I learnt from an English-speaking Dutch couple living in the city that Friday night tram transport wasn’t the most reliable so I headed straight back to the Airbnb where I could meet my Meg.
As I approached the foyer, there stood a well-travelled Meg. This exact moment marked the end of my solo trip, yet signified the start of the best sister trip I could have ever dreamed of. With every memory in front of us still to be lived.
Alarm set for the move to Lake Como bright and early the following morning and excitable Millie and Meg gradually dozed off and rested in preparation for the next day's trek!
More images from my trip can be found on my Instagram page through posts and highlights.
As just mentioned, this brings my solo trip to a close if you manage to make it this far. This is a little different from the ‘educational’ fashion content that I have previously created, but I started this passage, post-Italy travels and I have only recently picked it back up during this winter mourning period.
If you were thinking about taking that solo trip, DO IT. I can assure you that you’ll make it a regular when you get the bug.
Keep posted for the next Chapter of The Italy Diaries!
Millie,

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