One Day In Siena

Siena’s greatest importance to us today lies in her old medieval architecture and one day in Siena is bound to set you up for an amazing adventure with lots to see and do!

How to Get to Siena: Train, Car, Bus

Location: Tuscany, Siena Province

Taking the Scenic Routes

No doubt your itinerary is tight; Siena is filled with enough wonders to fill your day so taking side quests might not be for you.

Still…I can’t help myself.

The drive to Siena goes through the Tuscan countryside. Rolling hills of green undulating and unfolding as the miles turn a glorious sun overhead, and the smell of fresh cypress and grape in your nose. It is no wonder the Elysium fields in the minds of dying Romans are attached to the graceful fields of Val d’Orcia.

The most scenic route from Florence to Siena is the SR 222, a 2-hour drive that passes through Greve, Panzano, Castellina, Radda, and Gaiole.

And to let you know just how bad side-quests can make you miss your true quest…

The SR2 from Siena leads to Buonconvento then San Quirico d’Orcia, onto the SP146 that leads to Pienza and finally Montepulciano. You have missed the real prize [one day in Siena] but got the number ½ prize that was touring Val d’Orcia.

The Risanamento…that flew by Siena

A Short History on Siena

Risanamento is the name given to urban renovations and restorations that took place from about 1869. This was right about the time when Giuseppe Garibaldi was modernizing Italy and the concept of being Italian. Many restorations were going on in Italy, and many of the old architecture and sculptures in major cities like Florence, Milan, Rome, and others were being restored and even recast.

Risanamento seems to have flown by Siena…to our advantage. A walking tour of Siena lets you see just how Italian would have or could have looked had the love of art not come back to human consciousness.

Not to say that Siena is run down; Siena is old, a medieval city that once rivaled Florence in all her greatness in the 14^th – 15^th centuries. This also means that, like Florence, the Black Death also struck the city, with the exception that Siena never recovered like her sister. In 1555, aged, flailing, and failing, Siena was conquered by Florence.

Siena’s greatest importance to us today lies in her old medieval architecture and the whole medieval atmosphere in the city. If you are thinking about exploring Italian architecture, then one day in Siena is bound to set you up for the rest of your walking tours. Sure, there have been restorations, but most of Siena’s architecture is the old stuff, the good stuff from back when artists spent their entire lives on a single idea.

One day in Siena itinerary

1. Horsing Around in Siena

Yes, that is a thing in Siena, actually.

Siena has this massive square, the Piazza del Campo. Throw in the winding medieval carrugio, corso, vicolo, and largo [streets both wide and serpentine] and you have the Palio, Siena’s iconic race-horse event during summers on July 2 and August 16.

Not that the horses go into the narrow or wide streets or anything; that was just to set up the ambiance of the event.

During these two days, everyone finds their way to the Piazza del Campo. Then they arrange everyone in a central spot in the square itself. We – tourists and locals – become the barrier around which the horses run around.

It is an intense event. The ground is hard-packed clay, so dust is not really an issue. The issue s the crowds; everyone is cheering and screaming like crazy, competing with the nutcases on the horses running around us. It is the one day in Siena everyone is targeting and getting here, with all the crowds, is still worth it.

It gets crazier.

Right before the race, we see the jockeys chatting each other up, slapping backs, and encouraging each other. If you are lucky enough to be directly on the edge of the ring – and understand some Italian – you get to see the jockeys offering each other bribes and incentives to lose the match in favor of the other guy! They are doing this out in the open, one contrade/neighborhood outbidding the other or the win.

It gets even crazier!

I heard that betrayal is the icing on the cake during these negotiations. They take the bribe, then go on to lose the match to a different competitor…or win it themselves…or throw the match for no reason…or foul up their closest competitors to all lose! The combinations are crazy and this is why I am writing so much on this topic. My throat got raw and I still have trauma from all the screaming.

2. Walking around the Piazza del Campo

Thankfully, this madness lasts only two days a year.

Usually, the central square is a place of calm and contemplation. I should know; they deliberately designed the central square to make sure everyone looked out for each other. Think about it; you are planning an itinerary for one day in Siena and everything is already laid out in front of you on the same street.

The square’s design is something I don’t think I have seen most anywhere else. The buildings all face the center, and the panoramic shots you can take away from here will capture so many buildings you will walk away laughing.

The best shot is of the Fonte Gaia, the Torre del Mangia, and the Palazzo Communale. The Fonte is a fountain in the middle of the piazza, and is constructed of marble. There are different statues ringing the inner walls of the small pool of the fountain, telling a story I never got to hear. I hope you let me know.

The Palazzo is what you want in your view shot; it is an imposing brick and marble edifice and walking in gets you the chance to see some artistic works by Sienese masters like the Good and Bad Government frescoes by Ambrogio Lorenzetti.

3. Coffee in Siena

So, nothing says adventure like starting off the day with a mug of coffee in hand. I’m not kidding; the earliest trains from Florence can get to Siena by 5am or so, and those from Milan and Rome can also be finessed. So a coffee in the morning is just the way to shake off those legs.

Torrefazione Fiorella on the via di Citta, 13 was open by 7am and had some delightful pastries on the side. Bar Pinoteca on via S. Pietro, 38 is more accommodating, open 24 hrs a day, and was actually where we first dropped by before taking our first baby steps around the city. Basically, if you get to the central square you are bound to find a coffee place with pastries, bread, and cakes freshly set out and baked just for you.

Plus, I loved the early morning ambiance of Piazza del Campo. It was like people were gearing up for a race themselves, eyes glinting, checking out the competition and weighing whether to bribe them away, bribe and betray, bribe and lose. It was just one day in Siena in our minds but felt like we were about to embark on the race of our lives.

4. Siena Cathedral:

The Baptistry, the Crypt, and the Duomo of Siena

The Siena Cathedral is one of the most magnificent buildings I have ever encountered and the first place you should visit if planning on one day in Siena. Firstly, Siena’s buildings are rather low to the ground. But the Cathedral is a grand eminence that towers over everything and everyone. And that is not even counting the Cathedral tower, towering over everything else.

⬆️For the Cathedral Complex Pass with Audio Guide (OPA SI PASS)⬆️

The Cathedral is on the Piazza del Duomo, 8. It is Romano-Gothic, completed in 1348, and therefore grand and truly reaching for the heights. In old times, masons and artists from England, France, the Lowlands, and Spain would flock to Italy just to see the marvels of ‘new’ architectural ideas and the Siena Cathedral was one of these inspirations.

To the South, the nave remains unfinished, now serving as both a parking lot and a museum. This should be sad, but I rather see it as a testament to how Siena are proud folk, unwilling to coat a new building as if old just to sell the city.

Indeed, what the Cathedral has to offer is more than enough to establish it as a medieval architecture right up there with the best. The gargoyles and Saints and the mosaic of the Coronation of the Virgin on the façade are just one thing embellishing the immensity of the structure. The interior is another with the mosaic of the She-wolf of Siena on the floor. It is the entirety of the Gothic architecture that I appreciated most; all medieval and pitting medieval architecture in an original light.

I did some math and saw that the Baptistry, the Crypt, and the Duomo are where I spent most time during my day in Siena. The Crypt was sealed way back in the 1300s, and its re-opening in 1999 offered up ancient sculptures! The frescoes on the Baptistry establish Siena’s place right up there with any other medieval great; they are from Donatello, Ghiberti, and Jacopo della Quercia. As for the Duomo of Siena…the heaven-spanning arches peaking the green and white columns reaching up with the flags of old Medieval families gracing the columns are a sight to behold.

⬇️For Siena Cathedral and Piccolomini Library Entry Tickets ⬇️

5. The Piccolomini Library

This famous library within the Cathedral is noted for having no books, with what ‘books’ are there dedicated to the life story of Pope Pius II.

The oddity that is the Piccolomini Library is the frescoes painted around the walls tell more of the knowledge contained within the library than the books and manuscripts ever could. There is the Life of Aeneas Silvius Piccolomini frescoes. There are also many themes around allegorical figures, pastoral themes, Dionysian themes, bacchanalia, and others, most prominent among them Diana and Endymion and the Rape of Proserpina.

I advise taking the time to visit this library during your day in Siena. The idea behind the construction was to mimic French Cathedrals which, at the time, would build houses of knowledge around houses of worship, tying these two centers of enlightenment to each other. What it means to me is that Siena remained at the forefront of the medieval scene for as long as possible even as Florence was pushing her back.

6. Standing underneath the Torre del Mangia

Completed in 1348, the tower was another evolution in thought from both the medieval age and Siena herself. The dominance of her height over all of Siena was a pointed reminder of the secular power of the Council of the Nine right alongside that of the Church in Siena because of the bell tower’s own height of 88 meters. That means that from as early as the mid-1300s, even Italians were beginning to challenge the Church’s authority and this building confirms my theory.

One of the fun things tourists tend to do over one day in Siena is to climb the 300+ steps to the top just so they can capture the entirety of the city on their cameras. Just beyond the city limits are the Tuscan hills and countryside, a viewpoint whose shot was worth the strain on my calves.

Standing at the base, that devilish idea just can’t go away; you have to climb to the top!

The tower was like a quest; easy at first, where the steps are wide and the walls cheering you on. However, the road to heaven is difficult, and sainthood even more so. Towards the top the brick stairway narrows, the walls closing in on you, and you are tempted to go back down. Perhaps you were never meant to ascend too high?

But then, there’s a little window up top whose light passing through beckons you. That feeling of claustrophobia while climbing the stairway washes away, replaced by another. You ask yourself, is that blue the fountain? Are those people?

7. Wandering the Streets of Siena

One day in Siena is incomplete if you do not take the time to stroll her streets. It can feel abandoned, but only in the sense that the cobbled stone below your feet echoes your steps. Early morning just as your bus or ride arrives is best because the streets are emptier, and everyone is taking more time with their coffee.

The interesting part about the streets is the different neighborhoods you cross. The horse races are supported by the competing contrades or streets, and you will find they all have a distinct character different from each other. It will be difficult to tell them apart; the streets can be narrow, and the red of the walls can be even more difficult to tell the city streets apart.

8. Santa Maria della Scala

Believed to have opened in 898 AD, this is one of the oldest hospitals in the world and would have continued to hold this fame had it not closed in the 1900s.

Today though, it retains some of the grace it used to hold as it cared for the old, sick, dying, and orphans. There are frescoes from Domenico di Bartolo, Pietro Lorenzetti, Simone Martini, an altar triptych by Beccafumi, and other altarpieces by Bulgarini.

The Fonte Gaia’s sculptures, worn over time, are housed here. As a museum, the Santa Maria della Scala is a complex annex whose architectural and artistic value is immense. There are Etruscan cinerary urns and a Photo Library. The museum also hosts the Pellegrinaio, Cappella del Manto, Sagresia Vecchia, Cappella della Madonna, and the Oratories of the Compagnia di Santa Caterina della Notte, and the Oratories of the Compagnia di Santa Maria sotto le colte.

For me, it is the fact that it is from these old frescoes that so much of history comes down to us that I find fulfilling and fascinating. For example, did you know the names of Mary’s parents? Joachim and Anne! This hospital is one of the few in the world – perhaps the only one – telling the story of the life of Mary in her art.

9. Fortezza Medici

It was only in the mid-1800s that the Medici lost control over Siena. To retain this control, they built the fortress in 1561 on the Piazza Caduti delle Forze Armate. Like a fortress, it dominates its surroundings, making it the perfect place to take in the Tuscan countryside and take home some of that panorama.

10. Palazzo Publico

By now, you are running out of time to complete your tour, but can still squeeze a few more minutes before it turns from one day in Siena into an overnight in Siena.

The Palazzo Publico is a medieval structure that used to house their Council of Nine, the ruling political body in Siena that apparently had qualms about letting the Church have all the say.

It was completed in 1308, flanks the towering Tower of Mangia, and hosts several very interesting frescoes. Most frescoes depict Biblical scenes, allegories, Classical events, etc. These frescoes depict secular lives and works.

The Allegory of Good and Bad Government

Effects of Good Government in the City

Effects of Bad Government in the City

Again, Siena was indeed at the forefront of the change that was transforming Europe following the Black Death. This early in the stage, the Council of Nine was seeking ways to vindicate their grab of authority and like Machiavelli’s The Prince and other secular works of the age, the Sienese were at the front, showing the world a new way of power separate from the Church.

11. The National Picture Gallery

Another museum that hosts artworks from the 12^th – 16^th century over dozens of rooms.

One thing you will notice will be the plagiarism going on here. There are a staggering number of Madonna and Child pieces all over the place alongside other similarly themed works. Lorenzetti’s Annunciation, Duccio’s Madonna of the Franciscans, Freei’s Adoration of the Magi and Bartolo’s Nativity scene. My take is that the influence of the hospital, Santa Maria della Scala, somehow colored and characterized the artists here, drawing their brilliance towards the thee of Mary as a nurturer.

12. Wine in Siena

As you really really have to close your day in Siena, you must have some local DOCG and DOC. Siena is famed for her Vernaccia di San Gimignano, Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano.

Within Siena herself, many shops will sell Suenese reds and Vinsanto. Some of the wine shops I saw along the way are Gino Cacino on the Piazza Mercato, 31, Morbidi on the Via Banchi di Sopra, 75, and Cantina in Piazza on the Via Stalloreggi, 15. There are way more, I am sure. What we did was we picked a street and let the gods of the dice show us what they would.

Set the red aside; the Visanto was the most interesting to me. Amber in color, it is made from local grapes like Malvasia and Sangiovese. Most importantly, it apparently takes up to 3 years for a good Vinsanto to really bring out its flavor and aroma.

Close to and in Siena are some wineries I managed to find out about. Podere La Pace, Podere della Bruciata, Tiberini, and Castello Sonino were the biggest names on the lips of most locals and I wish I planned better to drop by them. Unfortunately, the architecture was what drew me to Siena and my main quest – One day in Siena – became a side quest. I am sorry!

Tips On Having One Day In Siena

1. Schedule a full day if you really want to enjoy Siena’s architecture to the fullest.
2. Skip the Palazzo Pubblico, and central square in favor of the view from the top of the Tower of Mangia, and the Santa Maria della Scala if you only have a few hours. The white and black of the Cathedral from the Tower, and the red of the Tower from the Cathedral might be all you want.
3. The Hotel Minerva, Hotel Santa Caterina, Hotel Duomo, the former monastery now Hotel Certosa Di Maggiano, and the Hotel La Colonna are really good places to stay. They are cheap, either close to the central piazza, or like Hotel Certosa Di Maggiano, continue to immerse you into the Siena ambience.
4. Try a cooking class from within the city or on one of the farmhouses via a private tour.
5. If you plan to spend some time in the hillsides of Siena as well, book an E-bike to move around because the hills are really hilly and will drain you and your timing.
6. Light clothing. Don’t fear the Summer Sun; Siena’s buildings are tall and narrow enough to offer very good shade.