Milan, Solo: 3 Days, No Apologies
I went to Milan on my own. Three days, three nights, a fitness training programme I wasn't about to let a city break interrupt, and absolutely no plan beyond "walk until something looks interesting."
This wasn't a couple's trip. It was mine and if you've read our piece on the solo travel boom, you'll know that's not new territory for me. It's just rarely the version of Milan anyone writes about.
Where I stayed, and why it worked
I based myself in Porta Venezia and ate locally most nights including one particularly excellent pizza at a spot called Savo, in the student village, surrounded by the kind of animated, unbothered energy that only a university neighbourhood has. My favourite pocket of the city, though, was Brera, the art district. I had lunch there, wandered the galleries, picked up boutique cosmetics I didn't need but wanted, and could have stayed for hours longer than I did.
The bit nobody warns you about
My first night, I sat alone at a local wine bar with a glass of red and a cigarette, surrounded by tables of animated locals who kept glancing over. A woman on her own, clearly not lost, clearly not waiting for anyone. I was entirely in my element. If you've ever felt self-conscious being the only solo table in a room, I'd tell you exactly what I told myself that night: let them look. You're not the one missing out.
The days
I was mid-training for a 100km bike ride for Lancashire Women at the time, so mornings started with a run, through the university campus, a nearby park, and a fair amount of dodging trams I clearly hadn't fully clocked the timing of. After breakfast, a self-guided walk through Brera took me to the Duomo and the Galleria, where I found an Aperol Spritz terrace with genuinely great views — even in February, even with tired feet. From there, tired feet and all, I made it to Santuario di San Bernardino alle Ossa — an eerie, oddly beautiful little church that's stayed with me since.
One day I took the train out to Lake Como, ran part of a lakeside route, picked up a picnic lunch, and headed back into the city feeling like I'd earned the evening. Another day started with a cab out to Navigli and ended with the walk back, taking in proper sundowner energy along the canal before a nightcap at a speakeasy-style bar with cocktails worth the detour.
And then there's the side of Milan we don't put here
Milan has a spicier side too, I found it, and it didn't require going far. But the honest, detailed version of that night where, what it was actually like walking in solo, what surprised me isn't one I put on a public blog. That's exactly what The Lounge is for.
Want the full, unfiltered version of this trip — including the club night? That's in The Lounge, faces revealed, nothing softened
[Join The Lounge — £8/month →]
