I’ll never forget the moment I first walked into Piazza del Campo.
It was late afternoon, golden light washing over those ancient brick buildings, and I just…stopped.
You know that feeling when a place hits you differently than you expected?
When I planned my Tuscany trip, Siena was supposed to be a quick day trip—a checkbox between Florence and the wineries.
But standing there in that shell-shaped piazza, watching locals sprawl out on the sloped pavement like it was their living room, I realized I’d massively underestimated this place.
Two days later, I was still there, still discovering hidden corners, still eating my weight in pici pasta.
So yeah, Siena got me.
And if you give it a real chance, it’ll probably get you too.
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Get Your Japan Guide NowStand in the Middle of Piazza del Campo and Just…Breathe
Piazza del Campo is the heart of Siena’s historic center and one of the most beautiful squares in the world, shaped like a shell divided into nine sections.
But honestly, those facts don’t capture what it feels like.
This isn’t just some pretty plaza you snap a photo of and move on from.
Built on the site of a Roman marketplace, its paving acts as a carpet on which young locals meet and relax, and the cafes around its perimeter are the most popular coffee and aperitivo spots in town.
I grabbed a sandwich from a little shop on one of the side streets, found a spot on the sloped brick, and just sat.
Watched tourists navigate the cobblestones.
Saw an old Italian couple sharing gelato.
Listened to the church bells echo off the medieval buildings.
It’s the kind of moment you can’t manufacture—you just have to let it happen.
If you’re visiting during summer, on July 2 and August 16, the square is covered with a layer of earth for the famous Palio horse race.
I wasn’t there for the Palio, but even on a regular Tuesday, the Campo felt alive in a way most historic squares don’t.
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When I first landed in Tokyo, I thought I was prepared. Spoiler alert: I WASN’T. 😅
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🎯 Grab Your Copy Now!Climb Torre del Mangia (Yes, All 400+ Steps)
Look, I’m not gonna lie to you.
Climbing the 400+ steps to the top of Torre del Mangia requires some energy.
There were moments on that narrow, spiraling staircase when I questioned my life choices.
But man, the view was worth the climb.
The Torre del Mangia is one of the symbols of the city, 102 meters high, and from the top you can enjoy a unique view of the entire city of Siena.
You see the terracotta rooftops stretching out in every direction.
The Duomo’s striped marble dome.
The rolling Tuscan hills fading into the distance.
My tip?
Go early in the morning or late afternoon.
The midday heat makes those stairs brutal, and you’ll be sharing that tiny viewing platform with way too many people.
The tower’s name comes from Giovanni di Balduccio, called ‘il mangiaguadagni’, who would often squander his earnings at the table—basically, “the eater.”
I love that Siena’s most iconic tower is named after a dude who loved food.
Get Your Mind Blown at the Siena Cathedral
I’ve seen a lot of cathedrals in my travels.
And I’m telling you, the Siena Duomo is one of my favorite cathedrals in all of Italy.
It’s a gothic masterpiece of striped marble with endlessly fascinating mosaics and an astonishing inlaid marble floor.
The facade alone is insane—this wild mix of Romanesque and Gothic with all these intricate sculptures and mosaics.
But it’s what’s inside that really gets you.
Those black-and-white striped marble columns.
The star-studded ceilings.
And that floor—oh man, that floor.
The exquisite mosaics of inlaid marble on the floor were created between 1373 and 1547 by more than 40 artists and feature Old Testament scenes, historical allegories and a parade of sibyls.
The thing is, the famous marble floor is only fully uncovered between late June and early July or August and October.
I wasn’t there during the uncovering, but even with parts covered, it was incredible.
If you can time your visit for when it’s fully visible, do it.
You won’t regret it.
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Get Your Japan Guide NowDon’t Skip the Piccolomini Library
So this is inside the cathedral, but it deserves its own mention.
Accessible from inside the Cathedral, the riot of vivid Renaissance frescoes covering every inch of wall in the small space was painted by Pinturicchio and his workshop which possibly including the young Raphael.
The contrast is wild.
You go from the Duomo’s solemn black-and-white striped interior into this explosion of color.
The frescoes tell the life story of Pope Pius II, and honestly, they’re so vibrant they look like they were painted yesterday.
I spent way longer in there than I planned, just staring at all the details.
The ceiling, the books displayed in glass cases, the way the light comes through.
It’s a small room, but it packs a punch.
And if you’ve got the main cathedral ticket, you’re already in—no extra admission needed.
🗾 I Wrote a Book About My BIGGEST Japan Travel Mistakes!
When I first landed in Tokyo, I thought I was prepared. Spoiler alert: I WASN’T. 😅
💸 I brought a suitcase that was WAY TOO BIG for the tiny hotel rooms and train aisles. I completely missed the last train because I didn’t understand the schedule. I spent HUNDREDS extra on things I could’ve gotten for cheap. Sound familiar?
“Things I Wish I Knew Before Going to Japan” is your shortcut to avoiding ALL my stressful mistakes. ✨ Inside, you’ll find practical, NO-NONSENSE tips on etiquette, transport, money, and hidden gems that will save you time, money, and a whole lot of confusion.
🎯 Grab Your Copy Now!Explore Santa Maria della Scala
This one surprised me.
Once a great medieval hospital, Santa Maria della Scala is a wonderful museum complex filled with frescoes, archaeological finds, chapels, and quiet underground corridors—it’s almost always uncrowded and yet is one of Siena’s most rewarding stops.
I’m talking about a place that brings together more than 1,000 years of Siena’s history, from the Etruscan and Roman ages through the Middle Ages to the Renaissance.
The Pilgrims’ Hall alone is worth the visit—with 15th-century frescoes on which Domenico di Bartolo also worked.
Then you descend to these underground tunnels that feel like you’re exploring some secret passage.
Because it’s not as famous as the Duomo, you might have entire rooms to yourself.
That’s the kind of travel experience I live for—discovering something incredible without having to elbow through crowds.
Take your time here.
Wander.
Get a little lost.
Wander the Medieval Streets with No Plan
Here’s the thing about Siena.
The “attractions” are great, but some of my best memories are from just walking.
Getting lost within the streets of the historical centre, following your nose down a side street, turning left instead of right, putting away Google Maps and just looking up—that’s where the magic happens.
The narrow alleyways that suddenly open into tiny piazzas.
The local shops selling hand-painted ceramics.
The smell of fresh bread wafting from a bakery you stumble upon.
I remember finding this little wine bar down some random street—no sign, just a wooden door and the sound of laughter inside.
Best Chianti I had the entire trip.
So yeah, have your list of must-sees.
But also leave room to just…exist in Siena.
Follow the cobblestones wherever they lead.
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I wasted THOUSANDS on travel mistakes you can EASILY AVOID. ✨ My book shares every lesson I learned the hard way in Japan—so you can have the smooth, amazing trip you deserve without the stress and extra cost.
Get Your Japan Guide NowVisit the Palazzo Pubblico and See Those Frescoes
Right on the Campo, you’ve got the Palazzo Pubblico—Siena’s city hall for almost 800 years.
Inside is the Museo Civico, and this is where you’ll find some seriously important art.
The museum has masterpieces of Sienese art, including the splendid 14th-century fresco of the Allegoria ed effetti del Buono e del Cattivo Governo by Ambrogio Lorenzetti—basically, “The Allegory of Good and Bad Government.”
I’m not usually a huge museum guy, but these frescoes hit different.
They’re massive, covering entire walls, showing what a city looks like under good leadership versus bad.
It’s political art from the 1300s, and it still feels relevant today.
Kinda wild.
Plus there’s a panoramic terrace where you can catch another gorgeous view of the city.
If you’re doing the Torre del Mangia, you can usually get a combo ticket that includes the museum.
Worth it.
Experience Wine in the Chianti Region
Okay, so technically this isn’t in Siena proper, but you’re in Tuscany.
You cannot skip the wine.
Siena is right in the heart of Chianti country, surrounded by vineyards producing some of the world’s most famous wines.
I did a half-day tour to a couple of family-run wineries, and honestly, it was perfection.
Rolling hills covered in grape vines.
Medieval castles perched on hilltops.
And the wine—oh man, the wine.
One place I visited was a woman-owned winery specializing in Chianti Classico.
Every bottle was fantastic.
Another had peacocks wandering the grounds and produced this incredible Merlot.
If you’ve got a car, you can drive yourself and designate a driver.
But I’d recommend booking a tour so everyone can drink and you don’t have to stress about directions.
The guides know all the best spots, including little places you’d never find on your own.
Eat Pici Pasta Like Your Life Depends on It
Let’s talk food for a second.
Siena has this thick, hand-rolled pasta called pici, and you need to eat it approximately 47 times while you’re there.
It’s usually served with a simple garlic and tomato sauce, or sometimes with a rich meat ragu.
Simple, rustic, absolutely delicious.
I had my best pici at this tiny trattoria down a side street from the Campo.
The kind of place with checkered tablecloths and a menu written on a chalkboard.
The pasta was perfectly al dente, the sauce was rich and savory, and I sopped up every last drop with crusty bread.
My advice?
Ask locals where they eat.
Or just wander until you find a place packed with Italians—that’s always a good sign.
Avoid the restaurants right on the main square if you want authentic food at reasonable prices.
Walk five minutes in any direction and you’ll find better options.
