What happens when a self-proclaimed pragmatist walks into a Tuscany wedding experience and leaves a hopeless romantic.
I have never been a romantic. I want to be clear about that upfront. I did not come to Florence looking for a revelation. I came because my husband got a wedding invitation, we said yes before we thought too hard about it, and suddenly we were booking overnight flights to Italy. That’s it. That’s the whole origin story of what turned out to be one of the most unexpectedly moving trips of my twenty years of travel.
A Tuscany wedding experience was not on my vision board. Weddings in general have never been on my vision board. But here’s what I’ve learned after two decades of showing up to places with my camera, my instincts, and increasingly — finally — a little bit of space where the itinerary used to be: the things you didn’t plan have a way of teaching you the most.
So let’s talk about Florence. Let’s talk about light through Medici windows, a film crew in a piazza, a cocktail bar that smelled like every good thing at once, and a rooftop in Tuscany where a woman who has never wanted to be at a wedding — not even her own — stood in a slightly too-formal dress among a sea of sundresses and cried her eyes out.
Pull up a chair. This one’s for us.
The Overnight Flight and the Sandwich That Lied to Us
We flew overnight — nine hours, direct — and landed in Rome to catch a high-speed train to Florence. Two hours, smooth, the Italian countryside doing exactly what Italian countryside does when it rolls past a train window: making you feel like your whole life has been slightly insufficient until this moment.
But first: Roma Termini. Fifteen minutes before boarding, starving, and there was a sandwich stand with the most gorgeous display I had seen outside of an actual restaurant. Mozzarella practically spilling off the bread. Fresh, beautiful, wrapped in paper and handed to us in a blue and white tote like we’d just made a boutique purchase.
We boarded. We unwrapped. We took a bite.
Cardboard. Absolute, gorgeous, beautifully packaged cardboard.
Fattorie Garofalo at Roma Termini — I see you. I will not be fooled again.
I tell you this not just for the warning — though please, consider yourself warned — but because that sandwich was Florence’s first lesson delivered early: a beautiful exterior tells you exactly nothing about what’s inside. Pay attention. Look closer. This applies to sandwiches and to everything else that matters.
Day One Was Not Day One — And That Was the Right Call
We checked into Il Guelfo Bianco around noon. A 500-year-old building converted to a hotel, our room with fifteen-foot ceilings and original wooden shutters that, once closed, made the entire world disappear. Florence outside. Silence inside. And my body, after nine hours in the air and two trains and a lying sandwich, sent me a message that was not a suggestion.
We are done.
For twenty years I would have argued. I would have pushed through, reset the clock by force of will, stayed vertical until a decent hour because that was the system and the system worked. But not that day, we closed the shutters. We slept. I woke up at 10 p.m. in the dark of a room that had no opinion about what time it was.
Here’s what I want you to hear, because some of us need this said out loud: stopping is not losing. Resting is not wasting. Sometimes the most powerful move you can make is the one that looks like nothing from the outside. We needed that day. It was the foundation everything else was built on.
Day One wasn’t lost. It was the setup.
The Medici Palace and the Light I’d Been Waiting Twenty Years to Catch
Day Two. Reset, rested, and without a single plan.
The Palazzo Medici Riccardi was two minutes from our front door. No advance ticket. No crowds. You just walk in — which, after twenty years of planning five days ahead for every major museum on three continents, felt almost transgressive. Just walk in. Okay then.
I should be honest with you: after twenty years of museums and castles across the world, there was nothing inside the Medici that would have floored me if I’d walked in as a tourist. The scale of the rooms, the tapestries, the art — it’s extraordinary in the way that very old, very serious things are extraordinary. Grand. Important. Present.
But I didn’t walk in as a tourist. I walked in as a photographer.
And that changed everything.
The light coming through those grand windows was strong and directional — the kind of light that stops your internal monologue cold and replaces it with pure seeing. I wasn’t judging the rooms. I was asking what I could do with them. How do you catch that quality of light in the detail of a tapestry? In the corner of a centuries-old doorframe? In whatever happened to be standing directly in its path?
My brain, which had been loud for weeks, went quiet. I moved through those rooms and I shot. No air conditioning. Ninety-seven degrees outside. Not a single regret.
This is what travel does when you let it — it hands you a new set of eyes. Not just for the place you’re in, but for the life you’re living. I wasn’t there to see the Medici. I was there to see what I could do with the Medici. There’s a difference, and it’s everything.
The Film Crew Nobody Told Us About
We left the Medici with no plan for the afternoon. Florence, as it turned out, had one for us.
We were walking — just following whatever street felt interesting, which is the only strategy that ever really works — when a film crew appeared alongside us. Cables, equipment, focused energy, police gently nudging pedestrians to the other side. We followed the energy, took a few side streets, and found ourselves at a small piazza café on the opposite side of whatever was being shot. We sat down. I ordered my first Hugo of the trip. We watched.
It was a chase scene for a Netflix show — the actor running full speed into the piazza, stopping hard on a mark. But what got me wasn’t the running. It was what happened the moment he stopped. The entire crew swarmed him instantly — circling, each person capturing the scene from a completely different angle, this gorgeous choreographed chaos all aimed at one still point.
And then there was the guy with the enormous boom mic on a stick. Running loops around the whole operation. Committed. Enthusiastic. Completely unbothered by how he looked doing it.
I turned to my husband and said: I want to be that guy.
Not the actor. The one running circles with the mic. The one in service of the thing being made — close enough to feel everything, free enough to keep moving.
We sat in that piazza for two hours. My husband, who can talk to anyone and frequently does, got us a conversation with the extras filling the crowd scenes. We ate tourist-grade pizza because hunger doesn’t negotiate. We watched take after take and I thought: we could not have planned this. We got here because we weren’t trying to be anywhere else.
Leave room. The thing you couldn’t have scheduled is usually the one worth writing about.
The Meat Capital of the World and the Woman Who Ordered Eggplant
Florence takes its meat seriously. I mean that as both enthusiastic endorsement and fair forewarning.
The Florentine steak at Osteria Giglio d’Oro arrives in portions measured in pounds — picture a T-bone, then make it five inches thick. My husband had them cut his in half. It was still a full meal. The markets — the Mercato di Sant’Ambrogio, the Mercato Centrale — display raw product in a way that is, let’s say, immediate. Skinned rabbits hung like still-life paintings. The kind of thing that lands in your nervous system before your brain has finished processing.
I discovered this while eating what was genuinely one of the best croissants of my life — buttery, flaky, the kind of thing that makes you reconsider every croissant you’ve ever eaten — while my husband cheerfully waved me over to inspect a Florentine steak directly beside skinned rabbits.
I walked away. I ordered the eggplant at dinner — roasted whole, no breading, served with sauce and good bread — and I felt magnificent about this choice. My husband looked at me the way he always looks at me when I make the sensible decision that he is incapable of making. We were both happy. We were both right.
Florence is a paradise if meat is your love language. If it isn’t, the eggplant will carry you beautifully. You’ll also have considerably more energy than everyone else at the table. Just saying.
La Menagerie: The Place That Smelled Like Every Good Thing
Friday night, a short walk from the hotel. Someone pointed us toward La Menagerie. Nothing about the outside prepares you for the inside.
You walk in and the first thing that reaches you is the smell — dried flowers, fresh flowers, candle wax — layered and present without being overwhelming, specific enough to tell you exactly where you are. Then your eyes start to land: paper, glassware, arrangements, candles, all of it displayed with the kind of deliberate care that tells you someone thought hard about every single inch of this room.
I walked the perimeter before I sat down. Touched things. Took it in slowly. And I thought: yes. This was made for someone like me.
The cocktails are constructed with genuine intention. I had The Marinara first — a savory martini with a frozen tomato standing in for ice, which I ate after I finished the drink because of course I did. Then The Cupid: strawberry, bright, the kind of thing you sip slowly because you’re aware it’s going to end and you’re not ready. For aperitivo I had a shrimp toast with caviar that cost twenty euros and required nothing else for the rest of the evening.
This is the place you go on a Friday when the week has been long and you need to remember that beauty is still a real and available thing. Go. Order slowly. Stay longer than you planned.
The Tuscany Wedding Experience That Had This Pragmatist Feeling All the Feelings
Saturday. The whole reason we came.
A cab out to Villa Medicea di Lilliano — the real Tuscany, rolling hills, afternoon gold, the sky doing something quietly extraordinary with the light. I was slightly overdressed. Everyone else was in sundresses. I never saw the original invitation. I made my peace with this in approximately thirty seconds because the view made every other consideration completely irrelevant.
I am not a wedding person and I want you to understand that this isn’t just a personality quirk. It’s a worldview. Pragmatists don’t do grand gestures. We do Tuesday mornings. So, weddings aren’t my thing. I don’t just mean I find them mildly tedious, I mean there has never been a single wedding in my entire life — not one — that I actually wanted to attend.
Not even my own.
My husband and I eloped. I was pushing forty and it was still the most monumental decision of my life — so monumental, so sacred, so entirely and completely ours, that I couldn’t share it. Didn’t want to. I, the pragmatist, also didn’t need an audience for the most important moment of my life. I just needed the right person and a clear head. That promise was between him and me, full stop. Some things lose something when you put them on a stage. Our love was one of those things, and I have never once regretted knowing that about myself.
I let go of gestures a long time ago. The Valentine’s roses. The anniversary bracelet. The grand public declaration. None of it has ever spoken to me — not because I’m cold, but because I’ve always believed those things are the performance of love, not love itself. What speaks to me is the daily commitment. The showing up. The ten thousand ordinary Tuesday mornings where you choose each other without an audience and without applause. That’s the profound thing. That is what I signed up for, and that is what I have.
Some people hear that and decide I’ve let go of romance. I understand why they think that.
But this Tuscany wedding experience is exactly why they’re wrong.
Because here’s what happened on that rooftop: they kept their vows to themselves.
No public recitation. No scripted declaration performed for the crowd. Whatever they promised each other, they kept it between them — intimate, private, entirely theirs. And something in my chest just unlocked. Because that’s it. That’s exactly it. Some promises are too important to perform. Some love is too real to shout from the rooftop, even when you’re literally standing on one.
The bride’s brother officiated, and you could hear the love underneath every joke he told — especially underneath the jokes, because that’s always where the realest feeling hides. His voice quivered right at the edges of the funny parts. We all heard it. Nobody said anything because we didn’t need to.
And the bride’s mother — too ill to travel, too loved to miss it — was there on FaceTime, the phone held up so she could see everything. The whole rooftop knew she was watching. Nobody pretended otherwise. Nobody needed to.
I am not a wedding person. I stood on that rooftop in Tuscany in my slightly-too-formal dress, surrounded by sundresses, and I cried. Not at the gesture of it. At the romance of it — the real kind. The kind that shows up in a brother’s quivering voice. In a mother’s face on a phone screen two thousand miles away. In two people who understood that what they were promising each other was nobody else’s business, and built their entire Tuscany wedding experience around that truth.
That’s romance. And if anyone has ever made you feel like letting go of the gestures means letting go of the magic — I’m here, from a rooftop in Tuscany, to tell you it doesn’t. It just means you finally know the difference between the real thing and the performance of it.
I wasn’t expecting to feel any of that. But that is the gift of leaving room.
The Cheeseburger That Closed Out A Tuscany Wedding Experience
From the rooftop: cocktail hour in the open air, a Hugo in hand, a golden field to walk across in the early evening light. Dinner served family style — sea bass, a risotto with celery and lemon that was better than it had any right to be. Good conversation. Genuinely good people. The kind of evening where you’re so deep in a particular exchange, laughing hard with near-strangers who are becoming less strange by the minute, that entire platters pass by without your noticing.
This is how I missed the Florentine steak.
Apparently it was served. Apparently it was extraordinary. I found this out in the cab on the way home.
My husband will tell you this is not the first time a version of this conversation has happened at a family gathering. That is all I am going to say about that. This joke lives here and nowhere else.
We had planned to close the night at La Menagerie — one last cocktail, a proper full-circle ending. But somewhere between the rooftop and the cab and the steak revelation, the question got very simple: do you want a cocktail or do you want to eat?
McDonald’s. Two cheeseburgers. Potato chips. Water.
It was exactly, perfectly right. There is something clarifying about the gap between the evening you imagined and the one you actually had — the Tuscan sunset, the rooftop tears, the kept vows, the good people — all of it landing softly at a fast food counter at midnight. No performance. No perfect ending. Just the two of us, fed and tired and full in every way that counts.
And maybe that’s what I finally understand about myself. The pragmatist and the romantic were never two different women fighting for the wheel. The pragmatist IS the romantic. She just shows up to love in a different dress.
The Details
STAY
- Il Guelfo Bianco, Florence — Heart of the city, steps from the Duomo and Palazzo Medici Riccardi. 500-year-old building, fifteen-foot ceilings, original wooden shutters that block everything. Exceptional breakfast. Find the corridor banquette for quiet mornings with your coffee before the room fills up.
EAT & DRINK
- Osteria Giglio d’Oro — Florentine steak by the pound. Ask them to cut it down. Extraordinary. Do not get distracted at dinner and miss the platter. Learn from my example.
- Pitta M’Ingolli — Local neighborhood piazza bar. No tourists. Two Hugos, free aperitivo snacks. Hot, no breeze, completely worth every minute.
- La Menagerie — Friday aperitivo essential. The Marinara, The Cupid, shrimp toast with caviar. Go slowly. Stay long. This place was made for us.
- Mercato di Sant’Ambrogio — Smaller, quieter market. Outstanding croissants. Go early before the inside stalls close. Brace yourself for the meat displays.
- Mercato Centrale Firenze — Worth a walk-through. Manage expectations on authenticity.
- All’Antico Vinaio, Florence — Worth the calories.
- Fattorie Garofalo, Roma Termini — The sandwiches look extraordinary. They are not. You have been warned.
DO
- Palazzo Medici Riccardi — No advance ticket needed. Uncrowded. Extraordinary directional light through grand windows. Essential for photographers. Walk in and just look up.
- Ponte Vecchio — Florence’s oldest bridge, built 1345. Full of jewelry vendors. Beautiful to see and walk. Do not buy the Rolex.
- Villa Medicea di Lilliano, Tuscan Countryside — Rooftop ceremony, alfresco family-style dinner, golden Tuscan sunset. The Tuscany wedding experience that started all of this is open for other experiences.
- Watch something being filmed in a piazza — we stumbled into the Netflix show Game Over entirely by accident. It was the highlight of Day Two. Keep your eyes open.
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