See Siena in one day, the perfect itinerary

Written By: Travel With Wally

A Town on Three Hills

Qualifying as Italy’s ultimate hill town, Siena sits atop three large hills granting you views of the surrounding Tuscan hills. You can see Siena in one day but you will probably end up wishing for more time. 

Siena once competed with Florence for power and ultimately Siena lost, but it did not lose its medieval feel.  While in Siena you will feel as though you have been transported back in time or to the set of ‘Game of Thrones’.  It is easy to imagine the life of those that lived there hundreds of years ago while wandering the streets or admiring the detailed architecture. 

Siena does have a tumultuous past full of war, famine, and disease.  But it found its luck during WWII as it was one of the few cities to escape any bombings. This is clearly evident when you visit, as it has been able to preserve its historical architecture, art, and medieval appeal. The ancient charm of the city will win you over again and again. During my travels in Italy, it remains one of my favorite cities for its beauty and current peaceful atmosphere. 

One Perfect Day In Siena

To see Siena in one day from Florence or Pisa is very doable and popular.  The train ride from Florence is less than two hours, allowing plenty of time to experience the famous city.  If your itinerary and timeline allow, I recommend spending the night in Siena and enjoying a pleasant sleepy morning venturing through the maze of small streets and alleys before the rest of the city awakens.  Be sure to stop for a cup of coffee and a fresh cornetto at one of the many coffee bars. Even if you can’t fit more than one day, a day trip to Siena is certainly worth considering.

Sites to see and Wandering to do

Piazza Il Campo

This piazza (or square) is one of the most famous in Italy. When coming to see Siena with only one day, make sure to put it on your list. It curves and slopes to resemble half of a giant clamshell.  On warm pleasant days, you can find people basking out in the sun on its gentle slope, but it was a bit too chilly for that when we were there. You can stop to eat at one of the restaurants or cafes lining the upper edge, enjoy a coffee or aperitivo in peace with no cars whizzing by. (Siena was actually the first city to ban cars from its city center (other than cabs and local residents) in 1966. I love that!)  You could even bring a picnic to enjoy while gazing at the beautiful and historical buildings surrounding you.  

Twice a summer the square hosts the Palio di Siena, a famous horse race where ten of the seventeen neighborhoods compete.  Each neighborhood has a unique mascot (wolf, unicorn, porcupine, etc.) and you will see their flags flying proudly during the event.  Keep your eye out while wandering the streets for the neighborhood plaques on the street corners. I had fun thinking about which one I would want to live in based on the mascot.  

City Hall

The pearl of the square is City Hall, located at the bottom of the piazza.  It is easy to spot with a 330ft tower, built around 1340.  At the bottom of the tower is an open chapel where the Palio contestants are blessed before their race, but historically it was built in 1348 as a thank you to God for ending the black plague.

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In the middle of the square, you will spot a unique fountain named ‘Fountain of Joy’.  It is a replica of the original fountain (found in Santa Maria della Scala), but it is beautiful and the engravings on the back panels show lady justice holding her scales and overseeing the free distribution of water.  The fountain was built to show the joy of the republic supplying free water to its citizens. 

The square is central to most of the sites you would want to see, which is great when you only have one day to see Siena. We decided we wanted to see the famed Duomo.

Duomo Complex (Duomo, Museo dell’Opera, Crypt, Baptistry) 

 ~2 hours

After visiting the charming Il Campo, we followed the street signs to the Duomo.  From most directions, the Duomo is hidden by surrounding buildings, so it is unveiled as you enter the complex. Now, just stop and stare for a while.  This is the most breathtaking Cathedral I have seen next to Florence.  The Sienese did not spare a penny for the production of this gothic beauty. It is adorned with statues, frescoes, and a beautiful round glass window.  After rewarding your eyes and soul with the exterior, go ahead and buy your ticket to enter. If you do only one thing with your one day to see Siena, going inside is a MUST.  

The ticket office is located in a corner in front of the Duomo.  You have several options to choose from including: 

• Entrance to The cathedral and library: €5 
• All Inclusive “Opa Si” Pass (includes cathedral, Piccolomini library, crypt, baptistry, and Museo dell’Opera): Prices vary from €8-€15 depending on the time of year.  Check for current prices here.
• The Gate of Heaven all inclusive pass (allows for you to climb to the top of the cathedral and all other sites included with the Opa Si pass): €20 

*All pass options and prices are available here  

*Prices are for adults, prices for seniors and children can vary in cost (usually less)

Entering the Cathedral

We opted for the Opa Si pass.  It is good for 3 days after purchase which allowed us plenty of time to visit all sections of the complex (even when you only have one day to see Siena, this is a great deal.)  I am sure venturing to the top of the cathedral would be magnificent, but with our pass, we were instead able to climb to the top of the unfinished facade of the new cathedral.  This allowed for stunning views of Siena and the surrounding Tuscan countryside.  

Because of Wally, Andrew and I had to take turns entering the cathedral and other sites.  Understandably, dogs are not allowed in historic monuments. 

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Duomo & Piccolomini Library

When you enter, you are greeted by towering pillars patterned with black and white marble stripes. Everywhere your eyes venture is dripping with magnificent artistry.  From the floors to the ceiling there are paintings, sculptures, frescoes, and mosaics.  Your eyes will feast on pieces done by famous artistic masters such as Nicola Pisano, Michelangelo, Donatello, and Bernini.

From here you can easily enter the Piccolomini library. Whatever you do, don’t pass up this opportunity.  Wall-to-ceiling frescoes cover the entirety of the room along with ancient texts.  Looking up you will see the vaulted ceiling also covered in intricate artistry.

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Museo dell’Opera

If you spend one day in Siena, I recommend you take advantage of your Opa pass and enter this museum.  It is full of art and artifacts from the cathedral, but my favorite part was climbing the steep and narrow stairs to the top of the unfinished facade for the new cathedral.  From here you can enjoy 360-degree views of Siena and the rolling Tuscan hills. 

Other than hosting a top-notch view, the museum is very interesting to wind through.  It won’t cost you much time as it is not very large, but it is worth a quick visit.  

Crypt

The crypt is exactly what I imagined a crypt to be like: dark and windowless.  It originally was a 12th century church but it was later filled in with dirt to support the weight of the cathedral towering above it.  In the 1990s it was excavated and had metal supports installed so guests can experience a once-forgotten part of history. 

Baptistery

We did not go to the baptistery on this trip, but it is on my to-do-list for our next visit.  The exterior is rich with adornments similar to its partner, the cathedral.  The interior is filled with art by early Renaissance stars, who, together, created a new font in the 1420s. This is truly a gem not to be missed and I am greatly looking forward to returning to see its treasures.

Get Lost

It may be a strange concept, but ultimately our favorite activity while in Siena was exploring the nooks and crannies and then wondering where in the city we had ended up.  Slowly wandering down the narrow lanes while gazing at picturesque window boxes and colorful scooters makes one feel that true Italian charm.  

As we were strolling along in the evening we came to an opening between the stone buildings and were greeted by a view across the valley between our current hill and the next.  Atop the neighboring hill sat the Basilica of San Domenico, a huge brick church with rays of light hitting it through the clouds.  We made our way to the peaceful plateau of the hill where it sits and gazed inside its quiet gothic interior.

Inside you can find a bust of St. Catherine along with one of her thumbs (carefully encased), her flagellation whip, and her skull covered by a clay mask.  

Around the back of the church sits the sanctuary and grounds of St. Catherine.  Pilgrims have regularly visited here since 1464 to pay homage to the Saint who convinced the Pope to return from France to Rome.  You are able to enter her home, which has been greatly embellished by artists and architects over time. But we decided to enjoy the surrounding grounds. 

This was by far Wally’s favorite part of the trip.  There is a large green area that has sweeping views of the countryside, olive trees, and a small dog park.  Wally enjoyed the grass, the smells, and meeting some fellow canine friends.  Even with only one day to see Siena, making time for Wally was important to us.

Relax

Food & Drinks

After spending one day in Siena exploring and discovering the city, you are probably pretty hungry.  There are many small restaurants and pizzerias around the historic city center to choose from, but if you have one in mind, I highly recommend making a reservation prior to arrival.  

Siena is famous for its pici, a pasta that resembles a thick spaghetti noodle.  A favorite way to enjoy this noodle is in Cacio e Pepe, a delightfully creamy and peppery dish.  This is a favorite of both Andrew and me.  Make sure to enjoy it with a delightful glass of wine or prosecco local to the region. 

In Conclusion

Andrew and I both fell in love with Siena and are looking forward to returning and spending even more time exploring.  When you find yourself on a day trip to Siena, I highly suggest you put the Duomo at the top of your list.  It really was the highlight of our trip.  There are many other sites to see and depending on your interests you can pick what you would like to do.  Some activities can be combined for a cheaper experience.  Just make sure to check the hours and if they are requiring reservations.  I have listed some of these sites and experiences below.  I am highly confident that you will enjoy your time in the beautiful city.  

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Other Sites to See (Pick and choose your day)

City Hall, Civic Museum, and City Tower

City Hall & Civic Museum

  City hall is still in use today for the Sienese government, but the top floor now houses the area’s civic museum.  Visiting will allow you to set foot in the place where the government separated from the church and became a secular society.  This then took hold throughout Tuscany followed by the rest of Europe.

In the museum, you will find some of the oldest frescoes in Siena depicting both the good and negative parts of governance.  The stories depicted in the ancient frescoes show the proud and humble depiction of Siena’s past.  

Cost: €10 & €15 combo ticket with City Tower & €20 to add Santa Maria Della Scala

Hours: Monday-Sunday 10:00-19:00 (ticket office closes at 18:15)

* hours may be shorter in the winter months

*Additional information can be found here

City Tower

Oh, how I wish I would have climbed the nearly 400 steps to the top of the tower.  We had decided to forgo this expense as we had been lucky enough to see the views of Tuscany from the Museum dell’Opera.  We are budget travelers, and although we had the time, we decided to take advantage of the time to explore the streets.  But I recommend that you take the opportunity as it is said to have some of Italy’s best views.

Cost: €10 & €15 combo ticket with Civic museum & €20 to add Santa Maria Della Scala

Hours: Monday-Sunday 10:00-19:00 (ticket office closes at 18:15)

* hours may be shorter in the winter months

* Additional information can be found here

Santa Maria Della Scala

Located directly across from the grand duomo, sits this large yet inconspicuous museum.  It once was the site of a hospital, orphanage, and sanctuary for pilgrims, but today guests are able to enjoy a host of art and artifacts.  It is even home to what is said to be a drop of blood from Jesus, a nail from the cross, and a piece of the virgin’s robe.  

It is also here that you will find the original statues from the ‘Fountain of Joy’, along with many intricate frescoes. 

Cost: €9 & €14 combo ticket with Civic museum & €20 to add the City Tower

Hours: Monday-Sunday 10:00-19:00 (ticket office closes at 18:15)

* hours may be shorter in the winter months.  

* Additional information can be found here 

Basilica di San Domenico & Sanctuary of St. Catherine

You will find the description of this giant hilltop church in our Wandering section. 

Cost: Free

Hours: Daily 7-18:30

Find out more here  

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How to get there (Via the Train)

 We are train goers! 

-some trips require transfers, but you can book direct with little to no price difference.

* Florence (Santa Maria Novella Station): 1.5-1.75 hrs, ~€9.50 

* Pisa Centrale: ~1.75hrs, ~€10.90

* You can buy your tickets directly from the station at the kiosks or ticket counter.  You can also pre-book them online on Trenitalia’s website or phone application (available in English).  You can also use the phone application “trainline”, which is what we like to use.

*It is also possible to take an express bus from Florence or a Taxi. Driving is not recommended due to a lack of parking, but it is possible.  

Station to Historic Center

Walking: leave the station and cross the small piazza into the shopping center.  Take the escalator up to the second floor and then proceed to the next escalator/stairs.  There are several sets of escalators that will take you to the top of the hill.  When you have reached the top, turn left and continue about .2 (5min walk) mile where you will see the wall of the old town (Porta Camollia). Enter and then you will follow Via Camollia (turns into Via dei Montanini) into the center. It takes a total of about 20 minutes to walk. 

Bus: Buy a ticket at the train station’s newsstand, cross the piazza into the mall.  Take the first escalator on the right down to the bus stop.  All buses go to the edge of the action, they either stop at Piazza Sale or Piazza Gramisci.  We recommend that you double-check with the driver that the bus is going to the center.  Ask “centro?”. 

Taxi: The taxis are available just outside the train station and cost about €8