Things to Do in Siena & Why to Stay Overnight

Two trips later and we still haven’t run out of things to do in Siena, Italy.  We, however, have had some magical experiences that allowed us to completely fall in love with this medieval city and the entirety of Tuscany.  Each time we stay in Siena, we stay a little bit longer.  

The same is true for other towns in Tuscany.  I never expected to love the hill towns of Italy as much as I do.  Originally, I thought we might be content to just take day trips from Florence, but I’m officially a believer that you should experience the cities of Tuscany outside of the throngs of day trippers and tourists.  Siena is no exception.  Assisi is no exception.  San Gimignano is no exception.  Pisa can be a stopover if you really want it to be, but the best way to experience Tuscany (and Umbria) is to stay in Tuscany or Umbria.

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Just a Few Things to Do in Siena

Take a Siena Walking Tour

This Siena Walking Tour starts at the Palazzo Pubblico and is a great introduction to the city!  After learning more about the campo and the Palio, our guide led us to one of the contrade museums.  This museum allowed us to see historical Palio costumes, flags, and tapestries depicting the win of a particular neighborhood of Siena.  It is an incredible look into the history of Siena and its “neighborhood” pride!  We would not have been able to visit the museum without this tour.

In addition to teaching us about the Palio history, our guide showed us some beautiful views of the Basilica Santa Caterina San Domenico and the Tuscan countryside as we wound through the narrow streets.  We stopped by the Siena cathedral (but did not visit it) and finished the tour at the Basilica of Santa Maria dei Servi.  We did not have trouble keeping up with our guide, but there were older people who struggled with the hills, so if you have limited mobility, this may not be the tour for you.

You can also book this Siena walking tour and include the Siena Cathedral.

Visit the Siena Duomo  & the Piccolomini Library

Built in the 13th century, the Siena Duomo is incredible.  There’s no other way to describe it. I cannot even imagine how big it would have been if it had been completed.  Thirteen years ago, I was entranced by the Sien Cathedral di Santa Maria Assunta’s starry ceilings.  (Yes, that’s its formal name.  The more you know…)  I was no less enraptured with it on this trip. This time, however, it was the Piccolomini Library that captured my awe.  The frescos, which depict the life of Pope Pius II, are delightfully colorful with rich, vibrant hues.  I didn’t remember that part from my previous adventure.

We took advantage of the audioguide offered by the basilica, which was great, but it was a little long for the late afternoon.  I suggest doing it earlier in the day or first thing in the morning.  If audioguides aren’t your thing, we also enjoyed the walking tour in this Rick Steves Guide to the Hill Towns of Italy.

You can purchase tickets in advance or from the office across from the Duomo, but the audioguide is purchased in the cathedral.

Walk the Old City Walls around Siena

We had hoped to visit the synagogue in Siena, but it wasn’t open early enough before we had to leave.  They have a particularly touching monument to the individuals who were lost in the Holocaust on a nondescript street in front of the synagogue.  From there, we chose to follow the old city walls around Siena.  This provides beautiful views and a look into daily life (it was Palm Sunday for us!).  We found the entire old city to be very well preserved.  I encourage you to duck into courtyards, watch for churches (there are many!), and enjoy the scenery.  It is the perfect way to see more of Siena than the Duomo.

Visit Santa Maria della Scala / Museo Civico

Similar to the Siena Duomo, the Siena Civic Museum offers beautiful art and artifacts from the 16th-18th centuries.  Make sure to check out the Ambrogio Lorenzetti frescos!  After viewing the art, if you’re feeling ambitious, you can climb the Tower del Mangia for 360-degree views of Siena and the Italian countryside.

Go Wine Tasting near Siena

My friend Grace swears by these wine tours of Tuscany.  We haven’t booked one yet, but it’s on our list. There’s also a more local option for wine tasting near Siena.  

Also on my list of things to do in Siena this Siena food tour.  It features local salami, cheese, truffles, and more – oh my!

Enjoy the Siena Campo

I’ll admit it.  We’re big piazza people.  We love to grab meals from the grocery store and people watch.  Siena’s campo is no exception.  Make sure to check out Jacopo della Quercia’s Fonte Gaia.  Not only is it a beautiful fountain, but it is also an engineering marvel!  It is one of the first hydraulic fountains to bring water into the city center in 1342.  There’s a fantastic supermarket to the right of the clock tower, and we made multiple trips there.  We spent blue hour here, and the blue contrasting against the siena brick was gorgeous.  Before heading back to our hotel for the night, we picked up gelato and made another stroll around the campo.  We spent the predawn hours here.  It was empty until around 10:00 on Sunday morning, so get up early and enjoy the city without so many tourists!

Where to Eat in Siena

We haven’t had a whole lot of luck with restaurants in Siena yet, but I’m committed to finding tasty food.  With each trip, I have managed to find a few more options in Siena, but I haven’t found a great Tuscan restaurant yet.  In most cases, we end up with overdone meat.  That isn’t the Tuscany way of cooking it, so I blame my fellow Americans.  Enjoy the food the way it’s meant to be eaten – the Tuscan way!

We did, however, discover La Proscuitteria, which was celebrating its grand re-opening.  It was CRAZY.  And – it is delicious.  (We even hit up the one in Florence twice.)  They created the most delicious open-faced sandwiches using fresh bread, olive oil, proscuitto and poppy seeds!  I cannot recommend this place enough.  My mouth waters every time I think about it!   This is a great place for lunch, a snack, or a light dinner.  (It is not a full service restaurant.  It’s part of a chain, but it is tasty.

Believe it or not, we did find a delicious hamburger in Siena.  I don’t travel to Italy for hamburgers, but when I do Al Buongusto is a great option.  I think we ended up there because it was one of the view places open late.  There isn’t anywhere to sit so you’ll want to find a place to sit or take it back to your hotel.

As far as gelato goes, I really enjoy Gelateria Kopakabana.

Where to Stay in Siena

There is no better place to stay in Siena than La Terrazza sul Campo.  The terrace on the field.  This small hotel offers four suites, all of which have a view of the Campo.  The Campo is the huge square where the Palio horse race is held every year.  In the evenings, you can take a passeggiata around the campo or grab an Aperol spritz and watch others make the circuit.    At La Terrazza sul Campo, you can enjoy the view from your balcony.  (When I visited Siena during my study abroad semester, I sat on the campo for a long time.  It is a truly beautiful square.)

La Terrazza sul Campo

Our first year, I booked the La Citta di Siena junior suite.  The second year, I booked the La Maesta suite. In both cases, few days before we arrived, I received an email from Viola with all the details about how to find the hotel.  This proved to be quite useful as our taxi driver had not heard of it.  I showed him the email and he knew exactly where to go.  We had a short walk through the pedestrian zone, but the hotel was easy to find.  Viola checked us in and gave us an order form for breakfast after escorting us to our room.  (She delivers your custom breakfast order to your room at the time you choose!)

La Terrazza sul Campo Suites

These junior suites are easily the size of an apartment.  There are beautiful frescos on the ceiling, along with beautiful tiling on the floors, but the huge windows that open onto the campo that capture my attention.  Both rooms had a small table and chairs, as well as a desk.  Tom and I both used the table to work, eat breakfast, and just enjoy the view.  On rainy evenings, we would pick up dinner from the Sapori on the campo and just enjoy the view.  There is also a small sitting area with more comfortable arm chairs, if you wanted to take time to read.  All rooms include a mini-fridge, as well as a tea kettle.

As far as the beds go, they are more firm than I expected, but I slept well.  The shutters keep the room quiet and dark, so you don’t have to worry about the noise from the campo keeping you awake.  The bathrooms are completely renovated.  Our rooms included walk-in showers with dual shower heads: rain head and handheld.  We did not experience any issues with hot water or water pressure.  The amenity basket in the bathroom included every sundry you could possibly want.

As an added bonus, the room offers air conditioning and we were able to stay comfortable without any issue.

STAY HERE: Find the best rate & book La Terrazza sul Campo.