Perched within Italy’s gorgeous Tuscany region, the medieval city of Siena is a totally stunning place to visit for a long weekend or part of a wider road trip through Italy’s best cities. With thousands of years of history, there are loads of the best things to do in Siena that are dotted all across this relatively small city. 

From the incredible towers, beautiful cathedral and historic piazza; your trip to Siena will be filled with spots to see. 

Now, for me, one of the things about Siena being a relatively small city is that it makes it pretty easy to stroll around. There’s no need for any metro lines, long bus journies or expensive cabs; just take a comfy pair of shoes and you can explore all of Siena with ease.

With this in mind, I wanted to show you some spots I’m hoping you’ll love across the city. Oh yeah, and remember, it’s quite easy to partner on a wider road trip between Florence and Rome, too. 

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Take a look, below, at the best things to do in Siena. Have the best time! 

1.) Torre del Mangia

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Built over 800 years ago, Torre del Mangia is right within Piazza del Campo and is one of Italy’s historic towers to see.

You see, when it was constructed, it was actually the tallest tower in all of modern-day Italy and still stands proudly watching over the Tuscan region. 

Interestingly, the tower itself was designed to be exactly the same height as Siena Cathedral. Apparently, or so I was told, this was to show the equal authority of the church and of governance in Siena itself. 

Now, although the tower looks high, it’s not too bad to scale for the views at the top. Just be aware it can get quite stuffy and busy at certain times. That being said, getting to the top is one of the best things to do in Siena. Trust me, the views are worth it. 

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2.) Piazza del Campo

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Best described as the beating heart of Siena, strolling through Piazza del Campo is a must-do when in the city; especially as there’s so much going on around the piazza itself. 

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Once here, be sure to spend some time exploring all the independent little bars, Cappella di Piazza and Loggia della mercanzia that line the square itself. 

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After exploring the square, pop into Osteria La Mossa for some of their salmon and their tasty burrata. 

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3.) Duomo

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Honestly, exploring the Duomo (or Cathedral) is, hands down, one of the best things to do in Siena. Plus, with the building being so impressive, you can’t miss it. 

Just be sure to book these tickets to Siena Cathedral that’ll help you skip the line and visit the beautiful Piccolomini Library, too. Just be sure to book these tickets before you arrive, they go quickly. 

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Once here, be sure to keep your eyes peeled for the incredible mosaics and look down at the floors. The marble floor took hundreds of years to create and is a must-see. 

Plus, you can check out their museum briefly (it’s only small) and see the crypt of the Duomo, too. 

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Afterwards, book a table for dinner at La Taverna di San Giuseppe that’s perched within the stone arches of this historic building. It has such an old-world charm that’s so lovely for dinner.

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Oh, and make sure to try their truffle pasta dishes; they’re so tasty. 

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4.) Piccolomini Library

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Part of the Duomo complex in Siena, the Piccolomini Library is not your average type of library. This place is totally palatial. Just take a wander around and you’ll know exactly what I mean. 

The centuries-old frescoes are just so beautiful to miss; it really is one of the best things to do in Siena. And, as I said before, book this queue jump ticket to the Piccolomini Library, which, also gets you into the Cathedral, too. 

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Accessed via the Duomo itself, you’d have to make a clear effort to miss it! 

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5.) Basilica Cateriniana

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The gothic basilica of Cateriniana San Domenico (the full name) has stood in Siena since the 13th Century. Again, this is the kind of place where centuries of art can still be enjoyed to this day.

After arriving, be sure to check out the Chapel of Saint Catherine, see the frescoes and pay attention to the walls of the naves; this is where you’ll find all the historic art. Including pieces by Casolani and Vannuccio. 

Also, if you fancy escaping the city and exploring the beauty of a Chianti vineyard, then book this incredible vineyard tour.

You’ll get to spend the evening in a Tuscan farmhouse, all whilst tasting some of the region’s best wines and a four-course Italian menu. Just make sure to book before arriving in the city, these tickets can fill up fast. 

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6.) Pubblico Palace

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Perched on Piazza del Campo, you’ll quickly realise (once you arrive) how walkable and compact the city of Siena truly is.  To get inside, book this Palazzo Pubblico ticket to enter.

Just don’t forget to spot the paintings on the walls within the Sala di Balìa. They date back to the 1400s. Plus, this ticket will give you access to the 14th-century gallery, Loggia dei Nove, which is just beautiful. 

Oh, and you can easily visit the palace whilst seeing the Tower of Mangia that’s right next door. If you get a chance to go inside, the Room of the Risorgimento is totally stunning and dates back centuries. 

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After working up a hunger, pop over to La Locanda dei Tintori which has one of the tastiest seasonal menus in Siena. Not only that, the dishes are so tasty and probably one of the yummiest places you can stop for food in the city. Their tagliolini with Italian truffles is everything and more!

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7.) Porta Camollia

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Nestled on via Camollia, walking through the city gate of Porta Camollia is one of the best things to do in Siena if you love the city’s medieval history.

You see, it’s one of the gateways to the medieval city of Siena and would have regularly been used as a way to protect the city from dangers (whilst guarding the road to Florence). 

Although you won’t spend longer than a few minutes walking through, you shouldn’t miss it. 

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8.) Explore more of Tuscany

Look, you’re going to be spoilt for choices on the best things to do whilst you’re in Siena; there’s no question about that! Though, if you’re planning a little gander outside the city limits, take a drive over to nearby Montepulciano (60-minutes away), or San Gimignano (45-minutes away).

Both are stunning cities and hilltop towns that are quintessentially Tuscan. We loved spending the day in these and it’s well worth visiting them if you’re got lots of free time, too. 

9.) Palio di Siena

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Held twice a year, the Palio di Siena is a historic horse race (of 90-seconds) whereby a horse will represent each of the city wards.

Dating back to Medieval times, it’s taken very seriously in Siena and very much part of the cultural web of the city; everyone comes out to enjoy the day. 

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After a day on the streets, make reservations at Tar- Tufo which takes fine-dining to a whole new level in Siena.

A little away from Piazza Del Campo, their tasting menu is incredible and their dishes are art. So so good! 

10.) Siena’s Medieval centre

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Of course, it goes without saying that you’re going to explore the medieval centre of Siena! Truth be told, you won’t be able to miss it. 

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Tough, do keep your eyes peeled for all the little cobbled alleys, artist studios and little shops that line the street.

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Oh, and for the best gelato, pop into Grom (and get yourself a good few scoops). Yum! 

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