I was walking through Navigli on my first night in Milan, heading toward a 4.8-star restaurant I found on Google Maps, when a waiter outside a bar waved me over. My first instinct was to keep going; I mean I had a plan. But then I thought, why not? The people there looked happy enough.
He sat me at a table out front, and I ordered a spritz (the only thing I drank this entire trip, and who knew there are so many kinds? Limoncello is my favorite one.) Once I settled in, Kindle in hand, I was ready for my favourite outdoor ritual: the triple threat — reading, eating, and people-watching.
Not long after, the same waiter lured in two more solo wanderers, seating us in a neat row at the front like some unspoken club. A guy next to me and a girl next to him. She had her Kindle too. I thought to myself, people passing must think this is the singles bar.
I was waiting for my menu when the guy asked if I wanted to share his. We started talking - about food, travel, where we’re from, and anything else that came to mind. Halfway through our pasta, we realised we didn’t even know each other’s names. We decided to turn it into a game: guess each other’s name before the meal ended, or part ways never knowing.
We managed to guess the first two letters before cheating with Google. His name was Charlie. We walked to the metro together and said goodbye — no contacts exchanged. That wasn’t the point.
It was the first evening of my six-day solo trip, and it gave me exactly what I’d been craving: the freedom to let plans be suggestions, to welcome detours, and to stay open. To the world, to strangers, and to my own thoughts.
This wasn’t my first solo trip, in fact it was my fifth, but every single trip has a different flavour. Some are pure rest and relaxation. Others are city breaks with parties, brunch, and art gallery visits. This time, I wanted a mix: city vibes, breezy boat cruises, great food, and some learning to spark my creativity.
It’s why I chose The Artist’s Way as my main book for the trip. Being on a solo trip in Italy felt like a perpetual artist date — everywhere I turned, there was something to inspire me. I also read The Kite Runner and even squeezed in a kdrama. I booked a Duomo tour through getyourguide.com and learned that the cathedral took almost 600 years to build and is home to over 3,400 statues.
I ate the most delicious food, picked up many random facts, and had to visit the pharmacy three times. Here’s something no one, not ChatGPT or TikTok, tells you about Milan: the mosquitoes in Navigli are relentless. Pack your mosquito spray and use it before you head out.
From Milan, I headed to the stunning Lake Como, where I visited Villa Balbianello — a must-see whether you’re a Star Wars fan or not. The ferry ride from Como was breathtaking and the villa itself was truly beautiful. I also took a day trip to Bellagio, a lakeside town two hours away on the slow ferry, and to Lugano, Switzerland — just 45 minutes by car, with its own beautiful lake.
Beyond the tasty food and beautiful scenery, what I loved most was the freedom to choose my own adventure each day — whether that meant curling up in bed at 7 p.m. with a book or heading out for a long sunset walk with gelato in hand.
Of course, solo travel isn’t always picture-perfect. There are lonely moments, and sometimes you have to navigate random challenges on your own. After five trips, here’s how I set myself up for success each time:
Do some research beforehand - having context helps you feel more at ease and in control
Bring what you need to be comfortable — I’m team tote bag
Pack basic meds (and now I’m adding mosquito spray to that list). Learn from my mistakes
Get in the mix - book a tour or activity that gives you a natural opportunity to interact with others
Don’t be afraid to make the first move - ask for help, give a compliment, or hand over your camera for a photo
Walk as much as you can - you find hidden gems, discover cool shops, and leave room for detours
Soak it in - be present and notice the small things, that’s the whole point
Have a rough agenda for each day, but stay flexible. On some days the plan is to make it up and that’s okay too
Bring a companion book or film, this gives your trip a rhythm and something to keep you busy when you need it
The idea of solo travel can be daunting, but I encourage everyone to try it. The world is far too big and interesting to wait for the perfect group to explore it with. Head out and get lost in the experience - there’s something inherently freeing about wandering alone and having uninterrupted quality time with yourself.
Beautifully written, Aisha! 💗
😍😍😍