The image I remember most from Florence in winter is not the Duomo, the steak or even the tiramisu. It is the view from Piazzale Michelangelo, with our tripods planted and the city spread out below us, looking almost like a snow globe in the winter light.
Florence did not stir my soul in quite the same way it has for friends who rank it as their favourite Italian city. That is not to say I disliked it. I just did not connect with it in the way I expected to.
We arrived a day before New Year’s Eve to a city packed with holiday crowds. After four carefully structured days in Venice, I had chosen to leave Florence largely unplanned. I wanted to see what would happen if I wandered without a long list of things to tick off.
Perhaps the crowds affected my first impression. Perhaps I was still tired and recovering from the cold I had stubbornly flown with. Either way, Florence did not sweep me off my feet immediately, but there was still plenty about it that I enjoyed.
Arrival in Florence and Another Monastery Stay
We arrived in Florence just before noon after a roughly two-hour train ride from Venice. 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 staying in monasteries. They are often simpler and quieter than regular hotels, and well located without the inflated prices. Ours was within walking distance of the historic centre, which meant we could drop our bags and head straight out.
The Magnetic Pull of the Duomo
The closer you get to the Cathedral of Santa Maria del Fiore (Cattedrale di Santa Maria del Fiore), better known as the Duomo, the harder it is to look anywhere else. Its façade is covered in white, green and pink marble, and the scale of it is difficult to appreciate until you are standing right in front of it.
We approached it from the rear first, where the marble looked darker, more weathered and stained by time and soot. By comparison, the front was bright, elaborate and ready for the millions of photographs taken of it every year.
It was the eve of New Year’s Eve, peak holiday season, and Florence was packed. I had 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 we arrived and I had already bought two paintings.
The first was from Alessandro (@cubetto_1967_), a street artist whose bright, saturated colours immediately drew me in. His paintings of Florence were playful without looking cartoonish.
The second was from another artist named Gazzi, whose work was completely different. His paintings used strong lines and minimal colour to create recognisable scenes of the city without too much detail.
I often wonder when I will finally have enough wall space in some future home to display all the art I insist on buying. For me, an original piece of artwork is a far better souvenir than a generic postcard.
Markets, the Arno and the Oldest Pharmacy
After buying art I probably had no wall space for, we continued wandering until hunger led us to Mercato Centrale. You can follow your nose in there, but sometimes an available seat is what determines where you eat. For us, it was F.lli Perini.
I ordered the eggplant parmigiana. My friend returned to the table with a plate piled improbably high with roast pork, which 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 and unapologetic taste of home. It was, after all, still Italian.
Properly fed, we walked it off through Florence’s leather markets, where vendors called out from every direction. “Lady, good price.” “Real leather.” “Special for you.” I briefly considered buying 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.
We eventually found ourselves beside the Arno River as the sun began to set. The stone buildings grew warmer in the fading light, while the water reflected streaks of gold and pink. We stayed there for a while, watching the colours change.
One place firmly on my list was Officina Profumo-Farmaceutica di Santa Maria Novella. It was founded in 1221, when Dominican friars 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 more like an old apothecary museum than a shop, with frescoed ceilings, glass cabinets and ornate wooden counters. The air was filled with a mixture of floral, herbal, citrus and powdery scents. Choosing what to buy required some restraint, but I still left with a few gifts.
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 the art or architecture. It was an analogue photo booth.
I mean the old-school machines that used to sit quietly in shopping centres around Singapore. The kind that took passport photos, printed grainy strips and somehow disappeared in the early 2000s. I think my last proper photo strip was taken in 2001 or 2002.
Florence still has them. Fotoautomatica is a small network of restored vintage photo booths scattered around the city. They take four photographs with no filters, editing or digital preview. You sit down, wait for the flash and hope for the best.
We found one just around the corner from our hotel, so that became our first stop of the day.
Florence was colder than Venice. I was layered well enough, but my skin still decided to protest by breaking out in hives from the cold, which I discovered is apparently a real thing. I also still had a lingering cough from the cold I had stubbornly flown with.
Any time we passed a pharmacy, I went in to look for propolis honey sweets, usually ginger and lemon. They were available everywhere and genuinely helped. 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 a studio and a shop, with larger works on the walls and shelves filled with stickers and postcards. His altered traffic-sign designs can be found all over Florence. He turns ordinary road signs into small pieces of visual commentary, and looking out for them became a bit of a game as we walked around the city. I left the studio with a small stack of stickers and postcards.
From there, we began the climb towards Piazzale Michelangelo to scout for our New Year’s Eve position. At the top is a bronze replica of Michelangelo’s David. The original is housed inside the Galleria dell’Accademia, but since we had not planned to enter the museum, I was perfectly content with this version. Think of it as a scenic consolation prize: David with a panoramic backdrop.
We continued uphill to the 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 elaborate enough to belong in museums, with marble angels, carved portraits and family vaults large enough to hold several generations. It was peaceful and almost park-like, although you naturally move a little more slowly and quietly out of respect.
After that, we made our way back down towards the city. Crossing Ponte Vecchio returned us immediately to the holiday crowds. The medieval bridge, famous for its jewellery shops and for being one of the few bridges in Florence spared during World War II, was shoulder to shoulder with visitors.
Minutes earlier, we had been walking among marble crypts in near silence. Now we were surrounded by camera straps, conversations in several languages and people slowly shuffling across the bridge
Steak, Wine Windows and Conserving Energy
Everyone says that when you are in Florence, you must try a Florentine steak. After much Google research and a bit of indecision, we ended up at Trattoria Dall’Oste.
I was hesitant because I am not a big steak person, and the idea of ordering a massive slab of beef felt slightly ambitious. When it arrived, I laughed. It really was massive.
The Chianina beef was tender, rich without being overwhelming and did not need heavy seasoning. I was also grateful that my friend has a hearty appetite because I would not have survived that portion alone. Not even half of it.
With all that food, more walking was inevitable. For novelty’s sake, we stopped at one of Florence’s many wine windows, or buchette del vino. These little openings in the walls date back to the 16th century, when noble families used them to sell wine directly to customers. Today, some have been reopened to serve wine, cocktails, coffee and even gelato through the window.
We then wandered back towards the cathedral to see what Alessandro had painted that day. His works sell 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 that’s why I was such a fan.
By then, we knew we needed to rest before heading out again for New Year’s Eve. We returned to the hotel, layered up and prepared ourselves for a long night.
New Year’s Eve Above Florence
Being the Singaporeans that we are, we were back at Piazzale Michelangelo a little after 9pm. This was our second climb of the day, and the temperature had dropped noticeably. I was wearing extra-warm Heattech, fleece and a scarf. I was prepared. Or at least I thought I was.
We chose our spot carefully. Photographers will understand. The clues were obvious if you knew what to look for, and I am not gatekeeping because the resulting photographs speak for themselves.
We set up our tripods and decided on our framing. And yes, in the spirit of full transparency, I wore a diaper. It was partly to protect our carefully chosen spot, but mainly because fighting an army of people for one public toilet cubicle in 7°C was not part of the plan.
The dedication was real. Sssshhhh…
The crowd grew gradually throughout the night, and fireworks went off sporadically from different corners of the city. At one point, people began waving those Harry Potter wand-type things that shoot fireballs into the air.
The narrow walkway behind us became increasingly congested, but people were surprisingly considerate. They saw our tripods and avoided standing directly in front of them, for which I was deeply grateful.
As we waited, I looked down at Florence lit softly in the distance. From up there, the city looked almost like a snow globe (yes, I know, I’m fascinated with snow globes at this point), close enough for us to feel part of the celebration but distant enough to watch it all unfold below. The fireworks appeared in scattered pockets across the city, less explosive and chaotic than Sicily had been the year before, but that was not necessarily a bad thing.
Part of the reason I travel at this time of year is because I like welcoming the New Year somewhere different. It is not just about photographing the fireworks. I want to experience how another city celebrates and what the atmosphere is like as midnight approaches.
Then midnight arrived.
Happy New Year.
If you are expecting a grand, choreographed display like those in Japan or Singapore, temper your expectations. New Year’s Eve fireworks in Italy tend to be more scattered. They are set off by different people in different parts of the city rather than forming one coordinated show. I suspect the elaborate displays are reserved for other holidays.
It was not the most spectacular fireworks display I had ever seen, but standing above Florence as the year changed still felt special.
Day 3: Slow Starts and One Last Photo Strip
Based on my experience in Sicily the year before, I already knew not to expect too many open shops or structured activities on New Year’s Day. Florence was noticeably quieter that morning.
We crossed back into Oltrarno, a neighbourhood I would seriously consider staying in if I returned. It feels more residential and is traditionally known as Florence’s artisan district, with workshops and small studios tucked between homes and cafés.
Our first mission of the morning was another Fotoautomatica machine. There were two couples ahead of us, but I did not mind waiting. The tonal quality from this particular booth was noticeably better than the first: brighter, with stronger contrast. This is the kind of technical detail only someone oddly invested in analogue photo booths would care about.
We wandered around until lunchtime, hoping that the trattoria we had saved on Google would actually open. On a public holiday, that is never guaranteed. When Trattoria Sant’Agostino finally opened its doors, it felt like a small victory.
It turned out to be the best meal of the trip. The prices were reasonable, the service was warm, and everything we ordered was excellent.
We followed the waiter’s recommendation and started with a whole onion stuffed with pecorino cheese. Not chopped. Not diced. An entire onion filled with cheese. It did not sound particularly promising, but ignore that instinct and order it anyway. It was rich, sweet, savoury and unexpectedly comforting.
Then came the pappardelle with wild boar ragù, followed by the tiramisu.
Tiramisu is subjective. It is like asking a Singaporean which stall serves the best chicken rice. Everyone has an opinion. I have eaten many versions of tiramisu in my lifetime: cake-like ones, overly sweet ones and others that were mostly ladyfingers. This one was creamy and light, without being too sweet. I would eat it every day if I could.
After lunch, we continued walking without any particular agenda. Eventually, we reached one final Fotoautomatica booth. It had the longest queue of the three and, ironically, produced the least perfect strip. The bottom frame had a light leak and was partially blacked out, but I suppose that is part of the unpredictability of using an old analogue machine.
We returned to the hotel to pack. The following morning, we had an early start and a six-hour train ride to southern Italy for the next leg of our self-imposed Amazing Race.
Florence did not become one of my favourite Italian cities, but I do not think every place needs to. I enjoyed our long walks, the art I bought, the photo booths, the food and, of course, welcoming another New Year from above the city.
If you are planning your own trip and want a more structured breakdown of where to stay, what to book and how to plan around the holiday crowds, I have also put together a practical Florence travel guide.(Coming Soon)