Discover Tuscany: Siena in One Day

Famed as one of the most beautiful cities in Tuscany, discover Siena’s main sights with me in one day…

Tip: This article is now available as a mobile app on iTunes and GooglePlay. Go to GPSmyCity to download the app for GPS-assisted travel directions to the attractions featured in this article.


Bathed in olive groves and Chianti vineyards to the north and the Brunello wine region to the south, picturesque Siena is a great base to discover Tuscany’s hidden secrets.

Siena’s surrounding three hills ensure steep alleyways and cascading steps down to splendid monuments, expansive piazzas and intimate arches, which make for exceptional images that are timeless…

You may have heard of Siena’s famous historic horse race the Palio, which dates back to the 14th-century and still occurs in July and August?

Bareback riders dress in their district city colours and race around Piazza del Campo with thousands of spectators cheering on – sadly, it’s December so miss this popular event.

Siena’s legend of the she-wolf

Wandering Siena’s medieval cobbled alleyways, it’s not long until you stumble upon Siena’s symbol – young twins being suckled by a she-wolf – in the form of a stone monument, sculpture, or art piece.

Siena’s legend on how it was founded is less than salubrious. The she-wolf was foster-mother to twin-brothers’ Romulus (Rome’s founder) and Remus.

The sons of Remus (Senius and Aschius) fled to the hills and founded Siena, following their father’s murder by his brother Romulus.

What to see

So much to see and so very little time…

Siena is believed to be first settled in 900–400 BC by the Etruscans. A must-see is Siena’s UNESCO World Heritage elegant Historic Centre, which dates back to the 12th and 15th centuries – a feast for the eyes.

What better way to explore when travelling than to not have anything planned or be time-constricted…just meander the cobbled paths and it’s not long until you’re confronted by yet another wonderful monument, medieval building, art piece, and spectacular site.

Porta Camollia

Enclosed by medieval walls, the commanding Porta Camollia graces the northern side of the wall but is not the original gate built in the 13th century as the original was destroyed during Siena’s siege in 1555.

Over the centuries, this gate that leads towards Florence was often the most defended. The original gate, built during the 13th century was razed during the 1555 siege of Siena.

Centuries of turmoil between Florence and Siena required the gate to be re-built.

Still visible in the western gate along Viale Vittorio Emanuele II are frescos dating back to 1585-89 by Siena’s painter Alessandro Casolani.

Fortezza Medicea

Following Siena’s defeat to Florence in 1554, the imposing fort was built 1561 and 1563.

The vistas from the fort are stunning.

Take a passeggiata (stroll) around the 1.5-kilometre-perimeter and park space to gauge its enormity before heading back to the historic centre.
Every corner opens a new chapter in history or a unique ancient panorama.

Piazza del Campo, Palazzo Pubblico, Torre del Mangia

The heart of Siena, Piazza del Campo’s shell-shaped design exudes finesse and is a popular meeting point also regarded as one of Europe’s greatest medieval squares’.

Built in 1338-1348, Torre del Mangia’s 102-metre structure dwarfs surrounding architecture – why not climb the tower’s 400-steps if you’re feeling energetic?

The Palazzo Publico (town hall) was constructed between 1297-1308 and almost every large room in the palace is home to frescoes.

Il Duomo – La Cattedrale dell’Assunta

A display of striking Italian Gothic architecture with a magnificent marble façade, the grand Duomo was built in the mid-12th century and the art piece of the Piazza del Duomo.

Statues by Michelangelo and frescoes by Italian artist Pinturicchio awaits the traveller inside…

Basilica of San Domenico

Soaring ceilings create a sparse but spacious presence in this basilica, built in 1226-1265 and also expanded during the 14th-century.

The basilica experienced damage during several fires between 1443 to 1531, then from military occupation from 1548 to 1552.

Partly unveiled frescoes and paintings adorn the impressive basilica as does a fresco representing Saint Catherine by another of Siena’s painters Andrea Vanni.

Flags fly proudly along timeworn alleys in Piano Dei Mantellini. Maybe this particular flag denotes one of the 17 contrade (areas) of the city – does anyone know?

Siena’s narrow paved streets are both steep and intriguing…

Street Scenes

Abound with photo opportunities around Siena’s streets, you don’t need to walk far before something unusual catches your eye…

The Blue Hour paints a colourful backdrop against the medieval city.

Shop windows are graced with traditional Christmas trimmings…

The chilly late afternoon mist blankets part of the city to create an eerie panorama.

Stroll along Piazza di Postierla until you gaze across to the centre of the piazza. A carved stone column stands high with the Sienese she-wolf flanked by the two sons of Remus (Achius and Senius).

A bronze eagle represents the Baptismal Fountain of the Aquila Contrada.

Getting there

From Pisa Centrale train station, it’s almost a two-hour train journey on Trenitalia to Siena (€10.80 one-way).

You change at Empoli and with only around 5 minutes between the connecting train, it’s a close call.

Today, both the train there and return train are late but still manage the connection each time.

Where to eat

Tuscany is heaven for a foodaholic, but then again what part of Italy isn’t?

Siena isn’t any different offering local delights in fabulous restaurants, Osterias, cafes, and snack places at every budget.

Il Vinaio di Bobbe e Davide

On Via Camollia 167, Il Vinaio di Bobbe e Davide offers a gorgeous internal building with great eclectic art and photos gracing its walls.

Rowdy and loud whilst serving local Tuscan food and with local wines. The Antipasto (€10) includes delicious salami, hard cheeses, Prosciutto, accompanied with freshly-baked bread – cover charge (€1.50pp) and half-litre of wine (€5.50).

Dinner doesn’t start until around 7:30 pm, which is early for Italy.

Owners are super friendly and joke around a lot – very welcoming.

Bar Perù

Along via Vittorio Emanuele 9, Bar Perù serves delicious savouries (€2.50+) in the pleasant outdoor seating amongst tall shading trees.

Bar Gli Archi

For great cheap coffee (€1+) and scrumptious pastries (€1+), check out Bar Gli Archi on via Montanini 154.

La Costrarella

La Costrarella on via di Citta 33, is a gelateria although not in the winter – pastries and savouries are served and dinner starts later in the evening.

Today we try the deliciously warming Vin Brulè (mulled wine – €3) to escape the bitter cold.

Leaving Siena

After an incredible but long day exploring Siena but still not seeing everything, sadly it’s time to leave the misty gate and take the return train to Pisa for a little rest.

Visit Nilla’s Photography for more global images. More posts on Italy.

Siena, Tuscany, Italy, Europe


62 thoughts on “Discover Tuscany: Siena in One Day

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  1. Hi! I’ve been following your web site for a while now and finally got the courage to go ahead and give you a shout out from Humble Texas! Just wanted to say keep up the great job!


  2. Great again. Sienna is very pretty. Only stayed a day when we were in Florence. Too short. The flag would be form one of the contradas. Which one I dunno.
    We have indeed crossed path several times. 🙂 On different Time continuums. Or Continua.
    Buona sera amica mia.

    Liked by 1 person

    1. Thanks for your comment – much appreciated and yes, one day in Siena is definitely too short.
      I’m a bit late responding as have been in the mountains without internet the last couple of days – bliss!
      Ha, ha how many languages do you speak?

      Liked by 1 person

    2. Have to go back to Sienna. 🙂
      No worry about time. One responds when one can. Those are relaxed exchanges. No business deadlines. 😉
      Haha. I am trilingual French, English, Spanish. I can speak Portuguese practically fluent. Spelling and grammar not that good. I can “masticate” enough Italian to get around. A bit of German, a bit of Dutch, and a little Swahili from my African days. 😉
      Needless to say, I love languages.

      Liked by 1 person

    3. Portuguese grammar and spelling us very archaic. I think it dates back to the 16th century and has not been modernized.
      The easiest? Depends on your native tongue. And whatever other language you speak. With Italian you could start reading French. Vocabulary is similar, more than Spanish. e.g Finestre, fenêtre. Sera, soir/soirée. Buon, bon, etc. It is often easier to read, because you have time to stay on one word and strip it of the “local” clothes. See the radical. If you’ve done Latin at school, it helps, because you have to understand what the radical of a word is.
      Au revoir. = A rriveder (ci) (A vous revoir)

      Liked by 1 person

    4. My native tongue is English and never learned Latin at school although my sisters did (I think). I never studied Italian, just spoke a mixed dialect when I was growing up, then didn’t speak it much for 30 years. 😉

      Studied French for 6 years in high school, but have forgotten too much. Thanks for the language lesson, you should teach languages!

      Liked by 1 person

    5. Probably even better that you learned Italian “at home” or a dialect. Makes it easier to pick up words.
      Français? Très bien. Il faut le pratiquer. For your next trip across the Alps.
      Au revoir Cara.

      Liked by 1 person

    6. Maybe but as my mother was from the north, father from the south, and relatives from all over, I ended up with a ‘misto’ of many dialects thrown in with Italian, so I’m confusing to many.
      Oui monsieur and yes, I defo need practice, although driving through France in Reg (motorhome) French was coming back to me. 😉
      Buona notte

      Liked by 1 person

    7. Yes, I’m understood, which is the most important issue. Although, a lot of the times friends or locals will correct me – my grammar or pronunciation makes them laugh! 😉
      Thank you – I’ll try and have some good dreams.

      Liked by 1 person

    8. LOL. It’s all right. That’s the way it is in any country. I’m sure if I when to the Land of OZ, some terms or expressions would fly way above my head.
      Hope you had good dreams.

      Liked by 1 person

    9. A good point and I’m sure we have enough colloquialisms to sink a battle ship! 😉
      No, had a yucky dream as reading Stephen King’s The Stand at the moment – probably not a great book to read before bedtime.

      Liked by 1 person

    10. Lucky I checked my Trash folder as this comment was in it – no idea why.
      Yes, it’s a riveting book and totally believable, especially with today’s global mindset, but you’re right, not really a bedtime read. 😉

      Liked by 1 person

  3. I am delighted to have found your blog. My husband and I walked from Lucca to Rome this past summer (Via Francigena). We absolutely loved Sienna — and I learned even more about it from reading this piece. I greatly look forward to reading more of your posts.

    Liked by 1 person

    1. This past July, my husband spent 24 days (actually 22 days + 2 full rest days) walking 400 km from Lucca to Rome. We took a slow, relaxed pace and saw incredible villages and scenery along the way. I posted each day on my blog. If interested, you can check it out on my site by searching Via Francigena or Camino. This was our 4th Camino walk. Our last one was 700 km.

      Liked by 1 person

  4. Alas, I was only able to experience Sienna for a couple of hours. Long enough to hang out in the famous square and discover the Italian version of pizza, and enough to wish we had more time there. Nicely photographed and described.

    Liked by 1 person

    1. Wow, a couple of hours is pretty short. I found one day was much too short.
      At least you got a taste of Siena – it’s definitely worth revisiting.
      Thanks for sharing your experience and the great feedback.

      Liked by 1 person

    1. Siena is a beautiful city and you’re right, one day isn’t enough time to see everything – think you could comfortably easily spend one week in Siena.
      For some strange reason I had to salvage your comment from my spam folder…


  5. As always, beautiful photographs telling the story of the place you’ve captured. Not around on your blog as I used to be, still wishing you’re thriving, dear Nilla. Sending a big hug. XxX

    Liked by 1 person

    1. My pleasure!
      It could be that I turned of the comments, for some articles I have done that yes. Slowly getting accustomed to a new normal, in general I am doing just fine 😉
      Are you still living in Italy?

      Liked by 1 person

    1. Indeed it is Francis and you’re probably right, some of these gorgeous cities and towns aren’t as busy as long ago.
      I hope that you get to visit Siena one day, although there’s so much more of Tuscany to explore yet…

      Liked by 1 person

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