The image I carry most from Florence in winter is not the Duomo, not the steak, not even the tiramisu.
It is the view from Piazzale Michelangelo. Tripod planted. City below. Florence resting beneath us like a snow globe in winter light. Close enough to feel part of it, distant enough to observe it.
Florence in winter did not stir my soul in quite the way it has for friends who rank it as their favourite Italian city. That is not to say I disliked it. Far from it. It simply moved differently.
We arrived a day before New Year’s Eve to a city dense with holiday crowds. After four carefully structured days in Venice, I chose to leave Florence largely unplanned. I wanted to see what would happen if I let it reveal itself without expectation.
Perhaps its magic was muted by the throngs of visitors. Perhaps I was still fatigued, recovering from a cold I had stubbornly flown with. It was colder here than Venice. On the outside I felt fine, layered well enough. Underneath, my skin had other ideas. I broke out in hives from the cold. Apparently that is a thing.
Florence did not romance me.
It asked me to stand still.
Arrival in Florence and Another Monastery Stay
We arrived in Florence just before noon after a roughly two-hour train ride from Venice. The shift from lagoon city to Renaissance heartland was immediate.
For this leg of the trip, we stayed at Casa per Ferie Regina Del Santo Rosario, another MonasteryStays booking. After positive experiences in Rome and Venice, I have grown fond of these accommodations. They are often simpler, quieter, and well located without the inflated prices of more commercial hotels. Ours was within walking distance of the historic centre, which meant we could drop our bags and head straight out.
And head straight out we did.
The Magnetic Pull of the Duomo
The closer you walk towards the Cathedral of Santa Maria del Fiore (Cattedrale di Santa Maria del Fiore), the more magnetic it feels. The marble facade commands attention. Crisp white, deep green and soft pink panels arranged with mathematical precision.
We approached from the rear first. That side was darker, weathered, stained by time and soot. It was a quiet reminder that beauty depends on where you stand. The front gleams for photographs. The other sides endure.
It was the eve of New Year’s Eve, peak holiday season, and Florence was packed. I made no plans to enter the cathedral and, honestly, had no regrets. Sometimes it is enough to stand outside and marvel at the marble. Heh. Nice touch.
Across the street, artists lined the pavement selling their work. It had not even been two hours since arriving and I had already purchased two paintings.
The first was from Alessandro (@cubetto_1967_), a street artist whose bold use of bright, saturated colours immediately drew me in. His interpretations of Florence felt playful without being cartoonish, expressive without losing structure.
The second piece I bought was from another artist named Gazzi. His style was entirely different. More restrained. Strong line work, confident strokes that formed recognisable scenes with minimal excess. Where Alessandro worked in colour, Gazzi worked in clarity.
I often wonder when I will finally have the wall space in some future home to display the art I insist on buying. For me, original artwork feels like a far better souvenir than any generic postcard.
Markets, the Arno and the Oldest Pharmacy
After buying art I probably had no wall space for, we wandered without urgency. Florence invites that. Its streets are compact enough that you rarely feel lost, but layered enough that you feel like you are discovering something.
Eventually, hunger caught up with us and led us towards Mercato Centrale. You can follow your nose in there, but sometimes an empty seat determines where you stay. For us, it was F.lli Perini.
I ordered the eggplant parmigiana. Sensible. Comforting. My friend returned to the table with a plate piled improbably high with roast pork, something that had apparently earned rave reviews. It tasted like an elevated version of sio bak, Cantonese-style crispy roasted pork belly. Even though I had declared this an Italian-food-only trip, I allowed myself a small, unapologetic taste of home. It was, after all, still Italian.
Properly fed, we walked it off.
From the market, we drifted through Florence’s leather stalls. The vendors called out left, right and centre. “Lady, good price.” “Real leather.” “Special for you.” I briefly considered a bag, but we still had many more days ahead and luggage space, in my world, is prioritised for food I intend to bring home.
Eventually we found ourselves along the Arno River just as the light began to change. Florence softens at sunset. The stone takes on warmth. The water reflects streaks of gold and pink. We lingered longer than expected, watching the sky shift slowly.
One place firmly on my list was Officina Profumo-Farmaceutica di Santa Maria Novella, founded in 1221 when Dominican monks began preparing herbal remedies in the adjoining monastery. There was a queue to enter, and this might have been the only line I was willing to stand in.
Inside, it felt less like a shop and more like stepping into a preserved apothecary museum. Frescoed ceilings, glass cabinets, ornate wooden counters. The air was layered with scent. Florals, herbs, citrus, something powdery and nostalgic. Choosing what to buy required restraint. I came away with a few gifts and the faint sense that Florence prefers to be experienced slowly.
Day 2: Photo Booths, Cold Air and Climbing for a View
If there was one oddly specific thing I had been looking forward to in Florence, it was not art or architecture.
It was an analog photo booth.
Those old-school machines that used to sit quietly in shopping centres back in Singapore. The kind that took passport photos, printed grainy strips, and somehow vanished in the early 2000s. I think my last proper photo strip was from 2001 or 2002.
Florence still has them.
The project is called Fotoautomatica, a small network of restored vintage photobooths scattered around the city. Black and white only. Four frames. No digital previews. Just step in, sit down, wait for the flash, and hope for the best.
We found one just around the corner from our hotel. That was the first order of the day.
It was colder in Florence than in Venice. I was layered well enough on the outside, but underneath my skin decided to protest. I broke out in hives from the cold, which, apparently, is a real thing. Add to that a lingering cough from the cold I had stubbornly flown with, and I developed a routine. Any pharmacy we passed, I stepped in for propolis honey candy, usually ginger and lemon. They were everywhere and genuinely helpful. I remember wondering why Singapore could not stock these in abundance.
From the photobooth, we crossed the Arno into Oltrarno and made our way to CLET Studio, the working studio and shop of French street artist Clet Abraham. He was not in that day, but the space functioned as both studio and store. Larger works hung on the walls, and the shelves were stocked with both stickers and postcards. His altered traffic sign designs are scattered all over Florence, playful interventions that turn ordinary road signs into visual commentary. Spotting them around the city became a quiet treasure hunt. I left with a small stack of both stickers and postcards.
From there, we began the steady climb towards Piazzale Michelangelo, scouting for our New Year’s Eve position. The higher we went, the more Florence revealed itself in terracotta layers.
At the top stands a bronze replica of Michelangelo’s David. The original lives inside the Galleria dell’Accademia, but I was perfectly content with this version, especially since we had not planned to enter the museum. Think of it as a scenic consolation prize. David with a panoramic backdrop.
We continued up to Basilica di San Miniato al Monte, one of the oldest churches in Florence, and wandered through the cemetery behind it. Italian cemeteries deserve their own category of travel. The tombs and crypts are intricate enough to belong in museums, yet here they sit quietly in open air. Marble angels, carved portraits, family vaults large enough to house generations. It felt peaceful, almost park-like, though you instinctively move slower out of respect.
From the quiet stillness of San Miniato and its hillside cemetery, we eventually made our way back down towards the city. The descent felt gradual, almost meditative, until it wasn’t.
Crossing Ponte Vecchio, we were thrust back into the crowds. The medieval bridge, famous for its jewellery shops and one of the few bridges spared during World War II, was shoulder to shoulder with visitors. The contrast was immediate. Moments earlier we had been walking among marble crypts in near silence. Now it was camera straps, chatter in multiple languages, and the slow shuffle of bodies moving in every direction.
Florence has a way of swinging between intimacy and spectacle within the span of a few hundred metres.
Steak, Wine Windows and Conserving Energy
Everyone says that when in Florence, a Florentine steak is a must.
Through much Google research and a bit of indecision, we found ourselves at Trattoria Dall’Oste. I will admit, I was hesitant. I am not a big steak person. The idea of ordering a massive slab of beef felt ambitious at best.
When the steak arrived, I laughed a little. It was massive. The Chianina beef was tender, rich without being overwhelming, with a depth that did not require heavy seasoning. It was simple and confident. I was also grateful my friend has a hearty appetite. I would not have survived that portion alone. Not even half.
With all that food, more walking was inevitable.
For novelty’s sake, we stopped at one of Florence’s many wine windows. Yes, they are aplenty. These small arched openings in the walls date back to the 16th century, originally used by noble families to sell wine directly to customers, avoiding taxes and, later, even avoiding plague-era contact. Now they serve everything from wine to espresso in tiny cups. It is charming, slightly theatrical, and very Florentine.
We drifted back towards the cathedral to see what Alessandro had painted that day. His works shift constantly, and I wanted to see if anything new had appeared. I ended up buying a smaller piece. His bright colours felt alive against Florence’s stone palette. It was different from the more traditional Renaissance aesthetic surrounding us, and maybe that was the point.
By then, we knew we had to conserve energy. Let me rephrase that. We had to conserve energy for our New Year’s Eve.
So we returned to the hotel, rested properly, layered strategically, and prepared for a long night ahead.
New Year’s Eve Above Florence
Being the Singaporeans that we are, we were back at Piazzale Michelangelo a little past 9pm.
It had already been quite the walk in the morning, and this was our second ascent of the day. The temperature had dropped noticeably. I was layered in extra heattech, fleece, scarf. Prepared. Strategic. Committed.
We chose our spot carefully. Photographers would understand. The clues were obvious if you knew what to look for. I am not gatekeeping. The images speak for themselves.
Tripods planted. Framing decided.
And yes, in the spirit of full transparency, I wore a diaper. Not just to protect our carefully chosen spot, but because the thought of fighting an army for one public restroom cubicle in 7°C was simply not part of the plan.
The dedication was real. Sssshhhh…
The crowd thickened gradually. Fireworks went off sporadically throughout the night, rogue bursts from different corners of the city. At one point, those Harry Potter wand-type things that shoot fireballs into the air appeared in multiple hands. The narrow walkway behind us became increasingly congested, yet somehow, miraculously, people were considerate. They saw the tripods and chose not to stand directly in front of them.
I was deeply grateful for that.
Standing there, looking down at Florence lit softly in the distance, I realised it was less about the photos or videos I would take. It was about intention. The intention to be there. To mark another year somewhere unfamiliar. To witness how another part of Italy moves through celebration. From up there, the city felt contained. Almost like a snow globe. Close enough to feel part of it, distant enough to observe it. A balance between peace and chaos. Not as explosive as Sicily had been the year before. Less chaotic. More measured.
Midnight arrived.
Happy New Year.
If you are expecting grand, choreographed fireworks like Japan or Singapore, temper your expectations. Italian New Year’s fireworks are more organic. Decentralised. Personal. I suspect the elaborate displays are reserved for other holidays.
Still, standing above Florence as the year turned felt significant. Not dramatic. Just deliberate.
Day 3: Slow Starts and One Last Photo Strip
New Year’s Day in Italy moves differently.
Based on my experience in Sicily the year before, I already knew not to expect much in terms of open shops or structured plans. Florence felt even quieter the morning after. No urgency. No agenda.
We crossed back into Oltrarno, a neighbourhood I would strongly consider staying in if I ever return. It feels more lived in. Less performative. Traditionally known as Florence’s artisan district, it still carries traces of workshops and independent studios tucked between residential buildings.
Our mission that morning was simple. Another Fotoautomatica machine.
This time there were two couples ahead of us in line. I did not mind waiting. The colour tone on this particular booth was noticeably better than the first. Brighter. More contrast. The kind of small technical detail only someone oddly invested in analog photobooths would care about.
We idled and wandered around until lunch, hoping the trattoria we had circled on Google would actually open. On a holiday, that is never guaranteed.
When Trattoria Sant’Agostino opened its doors, it felt like a small victory.
This turned out to be the best meal of the entire trip. The prices were reasonable. The service warm. And the food was, without exaggeration, the best of the entire trip.
We followed the waiter’s recommendation for an antipasti of a whole onion filled with pecorino cheese. Not chopped. Not diced. A full onion stuffed with cheese. It did not sound promising at first, but ignore that instinct and just order it. It was rich, sweet and savoury in a way that made no logical sense, unexpectedly comforting and easily one of the most memorable dishes of the trip.
Then came the pappardelle with wild boar ragu. Deep, earthy, generous. And finally, the tiramisu.
Tiramisu is subjective. It is like asking a Singaporean what their favourite chicken rice is. Everyone has an opinion. I have eaten a lot of tiramisu in my lifetime. Cake-like versions. Ladyfinger-heavy versions. This one was creamy and light without collapsing into sweetness. Balanced. I would eat it daily if I could.
After lunch, we did what we had been doing all along. We walked. No agenda. No checklist. Just covering ground and letting Florence unfold at its own pace.
Eventually, we made our way to one final Fotoautomatica machine. This one had the longest queue of all and, ironically, produced the least perfect strip. The bottom frame suffered from light leak and blacked out slightly.
Still, it felt like the right way to close out our time in Florence.
We returned to pack. The next morning would be an early start. A six-hour train journey down to southern Italy and onto the next leg of this self-imposed Amazing Race.
Florence did not sweep me off my feet.
But it left an imprint.
And sometimes that is enough.
If you are planning your own trip to Florence and want a more structured breakdown of where to stay, what to book, and how to plan around the holiday crowds, I’ve put together a practical Florence guide as well.(Coming Soon)