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The Ultimate Travel Guide to Siena, Italy

Siena is one of those places that just sticks with you. I’ve been twice now—once in December and again this past April—and both times felt totally different, but in the best way. When I went in April, it rained a lot, and yeah, it was kind of gloomy, but somehow that made it even more beautiful. The streets were shiny from the rain, the air smelled fresh, and the little cafés felt extra cozy. It just had this really calm, romantic vibe. December was a whole other experience. It was quieter, with holiday lights hanging between buildings and way fewer people around. It felt peaceful and a little magical, like the city was taking a deep breath. Siena really feels like a real-life storybook. Whether you’re having coffee in Piazza del Campo, walking through the old neighborhoods, or climbing the tower for the view, there’s just something about it that makes you want to slow down and take it all in. It’s one of those places that stays with you.


If you're thinking of visiting—even just for a day—this guide has everything you’ll want to know to make it count.



Getting to Siena, Italy

Both of my trips to Siena started in Florence—one by train, the other by car—and honestly, both were super easy and scenic in their own way.


By Train

From Florence, you can take a regional train to Siena in about 1.5–2 hours. The route is beautiful, passing through the rolling Tuscan countryside. Just keep in mind that Siena’s train station is a bit outside the historic center—it’s about a 20-minute uphill walk, or you can take a local bus or quick taxi ride into town. If you’re traveling from another major city in Italy (like Rome, Milan, or Venice), I highly recommend using Italo for your journey, it’s fast, comfortable, and often more affordable when booked in advance. From there, you can easily connect to a regional train or continue by car.




Tip: Try to arrive by mid-morning so you can enjoy the city before the crowds roll in. And if you can, stay until golden hour—Siena as the sun sets is pure magic.



By Car

On my April trip, I rented a car in Florence and drove through the Tuscan hills to Siena—and the drive was absolutely stunning, even with the rain. Siena is just over an hour from Florence by car, and the journey itself is part of the experience, with vineyard-lined roads, olive groves, and hilltop villages along the way.


If you're planning to explore more of Tuscany or nearby towns like San Gimignano, Val d’Orcia, or Montepulciano, having a car is definitely the way to go. I recommend booking your rental from the major city you're arriving in—like Florence, Rome, or Milan—for the best rates and availability. I used SIXT, and they made the whole process super smooth, from pickup to drop-off. Of course, you can go with whichever rental company you prefer—just be sure to book in advance, especially during peak travel seasons.


Just keep in mind that you’ll need to park outside the historic center of Siena, as it’s a ZTL (limited traffic zone). Parcheggio Santa Caterina and Parcheggio Il Campo are both solid options and just a short walk from all the main sights.




Tip: Download your offline map in advance, especially if you're driving through rural areas—cell service can be spotty in the countryside!



Things to Do in Siena, Italy

Siena is a small city, but it’s packed with beauty and history. Here are my favorite must-see spots:


Piazza del Campo

This is the heart of the city—and it’s stunning. It’s where the famous Palio horse race takes place twice a year. I loved sitting along the curve of the square with a cappuccino, just watching the world go by.


Siena Cathedral (Duomo di Siena)

I’m not religious at all, but the Siena Cathedral seriously took my breath away. The black-and-white striped marble, the insane level of detail everywhere you look, and the Piccolomini Library—just wow. It’s one of the most beautiful churches I’ve ever stepped inside.

Tip: Get the Opa Si Pass—it covers everything, including:

  • Cathedral

  • Baptistery

  • Crypt

  • Cathedral Opera Museum

  • Facade

  • Oratory of St. Bernardino (April to October)




Torre del Mangia

Climbing the Torre del Mangia is no joke—over 400 narrow, winding steps—but once you reach the top, the view is unreal. You get this full 360° view of Siena’s terracotta rooftops, Piazza del Campo down below, and the rolling Tuscan hills stretching out in every direction. It’s the kind of view that makes you stop and just take it all in. It’s a bit of a workout, especially if you’re not a fan of tight staircases, but 100% worth it. Wear comfy shoes and take your time—the payoff at the top is something you’ll never forget.




Palazzo Pubblico & Museo Civico

Right in the heart of Piazza del Campo, the Palazzo Pubblico is hard to miss—and it’s not just beautiful on the outside. Inside, you’ll find the Museo Civico, which is packed with incredible frescoes. One of the most famous is The Allegory of Good and Bad Government by Ambrogio Lorenzetti. It’s wild how something painted in the 1300s can still feel so relevant today. The art, the architecture, the history—it’s definitely worth a stop while you’re exploring the square.




Santa Maria della Scala

Santa Maria della Scala is one of those spots that a lot of people skip—and honestly, they’re missing out. It used to be a hospital, but now it’s this huge museum complex with tons to explore. There are underground tunnels, old chapels, ancient relics, and rotating exhibitions that cover everything from archaeology to contemporary art. It’s got this quiet, slightly eerie vibe in some parts, which just adds to the experience. If you’re into history or just want to see something a little different, this place is super underrated and absolutely worth a visit.




Basilica of San Domenico

The Basilica of San Domenico is free to visit and definitely worth a stop, even if you’re not religious. It’s where you’ll find the relics of St. Catherine of Siena—including her preserved head, which is both fascinating and a little intense. The church itself is pretty simple compared to others in Siena, but the history and significance behind it are powerful.


Tip: No photos or videos are allowed inside, so you’ll have to take it all in with your own eyes.


Walk the Contrade

Walking through the Contrade is one of the coolest things to do in Siena. The city is divided into 17 neighborhoods, each with its own emblem, colors, and identity—kind of like mini kingdoms within the city. You’ll see their flags, plaques, and symbols on buildings as you wander around. Some have animals like the wolf, owl, or unicorn, and each one has a deep history tied to Siena’s medieval past and the famous Palio horse race.


Tip: Keep an eye out for the different emblems as you walk—you’ll start to recognize which Contrada you’re in just by the decorations. It’s like discovering hidden stories all over the city.



Orto de’ Pecci

Orto de’ Pecci is a little hidden gem just a short walk from Piazza del Campo, but it feels like a total escape from the city. It’s a peaceful garden with grassy areas, farm animals roaming around, and even a small café. It’s the perfect spot to take a break, have a picnic, or just enjoy some quiet time surrounded by greenery. Super relaxing and completely free to visit—definitely worth wandering over if you need a breather from sightseeing.


Where to Eat in Siena, Italy

I ate so well in Siena—Tuscan food is hearty, rustic, and full of bold flavors. Every meal felt comforting and unpretentious, just really good food made with care. These places are all highly rated and have that local charm that makes the experience even better:


La Taverna di San Giuseppe

Tucked inside an ancient Etruscan cellar, this place is a local favorite for a reason. The atmosphere alone is worth the visit, but the food? Next level. I had the pici al tartufo here and I still think about it all the time—absolutely unforgettable.




Osteria Le Logge

Just a few steps from Piazza del Campo, this place strikes the perfect balance between elegant and cozy. The dishes are a creative take on classic Tuscan flavors, beautifully done without feeling too fussy. The wine list is fantastic, and the whole vibe makes it ideal for a special lunch or dinner.




Pizzicheria de Miccoli

This little deli near the Campo is easy to miss, but absolutely worth seeking out. They make some of the best paninis I’ve ever had, loaded with local cured meats and cheeses. It’s the perfect spot for a quick, casual lunch or to grab something for a picnic on the go.



Osteria degli Svitati

Tucked away from the main crowds, this cozy little spot has a super local feel and seriously good food. I had the wild boar pasta on a chilly day and it was exactly what I needed—comforting, rich, and full of flavor.


Ristorante Tar-Tufo

As a huge truffle fan (seriously, it’s one of my all-time favorite things), this place was a dream come true. Tucked near the Duomo, it’s a small, intimate restaurant that puts truffles front and center in the most delicious way. The dishes are elevated but still feel warm and comforting—basically everything I love in a meal. If you’re even remotely into truffles, don’t skip this spot.




Tip: Try pici—Siena’s famous hand-rolled pasta. I had it both cacio e pepe-style and with wild boar ragù, and both were absolutely perfect.


Best Coffee Shops in Siena, Italy

Wherever I travel, I have to check out the local coffee scene—it’s kind of a non-negotiable for me (and honestly, the whole reason my blog is named what it is!). Between sightseeing and long walks around Siena, I found some cozy coffee spots that I absolutely loved:


Caffè Nannini

One of Siena’s most iconic cafés, and for good reason. Their ricciarelli—soft almond cookies—are incredible. I went both mornings during my December trip and it quickly became a little ritual I looked forward to. Great coffee, cozy atmosphere, and that perfect old-school charm.


Pasticceria Buti

This place is popular with locals, and once you go, you’ll get it. The pastries are absolutely divine, and it has that classic Italian coffee bar vibe where everyone’s standing at the counter for a quick caffeine fix. I’m a cappuccino kind of girl, so that’s my go-to—and paired with one of their pastries? Pure happiness.



Torrefazione Fiorella

This little spot may be small, but it serves up some of the best espresso in Siena. It’s no-frills, super local, and perfect for a quick pick-me-up between exploring. Even though I’m usually a cappuccino girl, I had to try the espresso here—and it did not disappoint.


Caffè la Piazzetta

Tucked near the Duomo, this quiet little café has outdoor seating that’s perfect for slowing down. I sat here with a cappuccino, did some journaling, and just soaked it all in. It’s a great spot if you want a peaceful break or some low-key people-watching away from the crowds.


Where to Stay in Siena, Italy

In December, I stayed in a charming little Airbnb right in the heart of Siena’s historic center. It was small and cozy, with a sweet view of the rooftops—perfect for chilly winter nights and slow early morning walks. Total main character vibes.

If you're more of a hotel person, here are some amazing options to check out:


Grand Hotel Continental Siena – Starhotels Collezione

A 5-star hotel in a 16th-century palace just steps from Piazza del Campo. Think frescoed ceilings, antique decor, and an underground wine cellar. It’s luxury with a ton of history.


Hotel Certosa di Maggiano

Set in a former monastery just outside the city walls, this place is surrounded by olive trees and vineyards. It’s quiet, peaceful, and comes with a pool, tennis courts, and rustic-chic rooms. Perfect if you want something relaxing but still close to everything.



Palazzo Ravizza

A beautiful historic hotel with a garden terrace that overlooks the Tuscan countryside. It’s got vintage charm and is within walking distance of all the main sights—great for a romantic stay.


Hotel Palazzo di Valli

This one’s in an 18th-century villa just outside the center. Gorgeous views, super welcoming staff, and that classic Tuscan feel. It’s a little more low-key but still convenient.



Villa Scacciapensieri

A bit farther out, but ideal if you’re looking for countryside relaxation. The villa has big rooms, pretty gardens, and a pool—perfect for unwinding after a day of exploring.


All of these are solid picks depending on your vibe—whether you want to stay right in the middle of the action or unwind just outside the city.


Best Time to Visit Siena, Italy

I’ve been to Siena in both spring and winter, and honestly, each season has its own kind of magic.

April was full of life—mild weather, flowers blooming everywhere, and perfect for wandering the city, having lunch outside, and climbing up for those epic views. Everything felt bright and buzzing, but still not overwhelming.

December was a whole different vibe—quiet, cozy, and super charming. The festive lights were up, the crowds were gone, and I barely waited in line for anything. Staying in an Airbnb made it feel even more relaxed and personal, like I was living in my own little corner of Siena.



If you’re still figuring out when to go, here’s a quick breakdown:

  • September–October is also a great time: the wine harvest is in full swing, the lighting is golden, and the weather’s still warm during the day.

  • July–August can get hot and packed with tourists, but if seeing the Palio is on your bucket list, this is when it happens. Just make sure to book early—and be ready for crowds.



Siena is a place that invites you to slow down. It’s not just about checking off attractions—it’s about enjoying every step through its winding streets, every sip of wine, every bite of pasta. Both times I visited, I left feeling full—in every sense of the word. Whether you’re visiting for a few hours or staying overnight, Siena is a city that knows how to leave a mark. And if you’re anything like me, you’ll already be thinking about when you can come back before you even leave.

Have you been to Siena? I’d love to hear what you loved most.


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