The swallows fill the skies above Siena at daybreak. From their rooftop nests, these aerial acrobats dart and swoop through the air, tracing elegant arcs against the backdrop of the city’s medieval buildings and the Tuscan hills beyond.
But they are more than just seasonal visitors; they are a living connection to Siena’s storied past. They have been part of the landscape for centuries, their annual return marking the passage of time as much as the ringing of the Basilica of San Domenico’s bells.
Siena has barely changed since its 14th-century glory days, when it was Florence’s fiercest rival. Florence won the political and economic battle, but Siena still holds its own when it comes to visitors’ hearts.
Narrow streets radiate from Italy’s most magnificent square, Piazza del Campo, draping themselves across the three hills on which the city is built. At its centre sits Tuscany’s most dazzling cathedral and tallest tower, Torre del Mangia.
Siena is an easy day trip from Florence, but it deserves more than a rushed visit. This is a city to take slowly, not one to tick off a list.
Here are my favourite things to do in Siena.
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1. Stroll around the setting for Il Palio
Siena has been divided into administrative wards (contrade) since the 13th century, each represented by a mascot and a set of colours. They continue to play an active role in the city, their territories marked by colourful banners, wall plaques and lamps.
Contrada pride reaches its peak during Italy’s most spectacular festival, the historic Palio horse race, or Il Palio, held in Piazza del Campo on July 2 and August 16 each year. Ten riders representing these contrade compete fiercely in a 90-second race, a spectacle reflecting centuries of rivalries.
The shell-shaped, red-brick square Piazza del Campo is one of Italy’s most recognisable squares. Low buildings cling to its curves, allowing sunlight to flood the square.
Fonte Gaia is a 19th-century copy of the original fountain by Jacopo della Quercia. Fed by underground viaducts, it was once Siena’s main source of drinking water. Two small fountains still supply thirsty visitors today.
2. Step into history at Palazzo Pubblico
Il Campo slopes gently to the Gothic Palazzo Pubblico on its southeast side. Built between 1297 and 1310, it was the seat of the Council of Nine, nine elected officials who kept the peace, ran the economy and administered justice during Siena’s medieval heyday.
Inside, Ambrogio Lorenzetti’s frescoes, Allegory of Good and Bad Government, show the Council’s vision of an ethical, well-run city. The Sala del Mappamondo and Sala della Pace are wallpapered with further frescoes by Lorenzetti and Simone Martini, connecting Siena’s artistic and political history.
You can buy a joint ticket covering Palazzo Pubblico, Torre del Mangia and Santa Maria della Scala from the ticket office on the day of your visit (not available online). Tickets for the palace alone are also available. Palazzo Pubblico is open daily from 10 am until 6 pom or 7 pm depending on season (check here).
3. Scale Siena’s medieval skyscraper
Soaring over the city’s brick buildings like a giant exclamation mark, Torre del Mangia was designed to rival the height of the cathedral’s campanile, symbolising the secular power of the Republic of Siena. Its name is taken from its first bell-ringer, Giovanni di Balduccio, nicknamed “Mangiaguadagni” (profit eater) due to his reputed fondness for food and spending.
Your reward for climbing to the top of Torre del Mangia is an unbeatable view over Il Campo and Siena’s red rooftops. But make no mistake; this is a challenging trudge up narrow, winding staircases (I skipped it).
Torre del Mangia does not offer online booking. Visitor numbers are limited, and your best bet is to secure an entry slot at the ticket office at the start of your day in Siena.
4. See the Duomo, Siena’s spiritual masterpiece
If Siena’s civic pride is manifested in Palazzo Publico and Torre del Mangia, the Duomo is its spiritual one. Dazzling inside and out, Siena Cathedral is a confection of striped columns, inlaid marble floors and side chapels stuffed with artwork.
There’s a hexagonal pulpit by Pisano and sculptures chiselled by Michelangelo, Donatello and Bernini.
The Piccolomini Library, with its vibrant frescoes by Pinturicchio, depicts the life of Pope Pius II and is a masterpiece of the early Renaissance.
I upgraded to include the Gate of Heaven (Porta del Cielo), a walk through the cathedral’s vaults and along the terrace around the dome. It was rushed, and netting above the cathedral floor blocked much of the view. I wouldn’t bother again.
5. See the cathedral’s treasures at Opera del Duomo
Siena Cathedral Museum (Opera del Duomo) is home to some of Italy’s artistic masterpieces.
Sala Duccio houses Maestà by Duccio di Buoninsegna (1260 – 1319). Duccio was the Sienese artistic rockstar of his time, and he painted this extraordinary panel for the Duomo’s high altar.
His circular stained-glass window, created for the cathedral’s east end, is also in the museum.
6. Walk along the Unfinished Façade (Facciatone)
In 1339, Siena’s council planned to expand the cathedral into the largest in Christendom, outdoing Florence’s Santa Maria del Fiore. Work began on a new nave at the southern end, with the 13th-century cathedral set to become its transept, part of the so-called Duomo Nuovo.
Then the Black Death hit Siena hard, scuppering these lofty ambitions. I walked along the viewing platform on what would have been the cathedral’s entrance façade and was treated to the best views in town.
7. Visit Santa Maria della Scala, one of Europe’s oldest hospitals
Founded in the 9th century, Ospedale di Santa Maria della Scala is located directly across from the Siena Cathedral. For centuries, it served as a refuge for pilgrims, a centre for medical care and a hub for charitable activities, reflecting the medieval values of hospitality and communal support.
Today, Santa Maria della Scala is a museum, with exhibitions highlighting the interplay between faith, medicine and community life in Siena. Its vast subterranean tunnels offer a glimpse into the hospital’s operational infrastructure and exhibit the museum’s Etruscan finds.
I’s star attraction is the 14th-century Pilgrims’ Hall (Sala dei Pellegrinaio), a room filled with frescoes illustrating the hospital’s history.
8. See a religious relic at San Domenico
Catherine of Siena, born in 1347, was an Italian mystic, theologian and member of the Dominican Order. She spent her life serving the poor and sick, and campaigning for peace and church reform.
She was canonised in 1461, and you can view her head in the austere Basilica di San Domenico. Mercifully, photography is not allowed.
9. Leave time to get lost in the streets of Siena
As wonderful as these sights are – and they are fabulous – much of the joy of Siena comes from exploring its winding streets and views across the Tuscan countryside. It’s loveliest in the evening, once the day trippers have gone and the city empties out.
All that remains is to pick a favourite restaurant and settle back with an aperitivo. Saluti!
Practical Information
Tickets for Siena Cathedral: A quick explainer
Siena Cathedral is part of the Monument Complex of the Cathedral, which also includes:
You can visit the Cathedral and Piccolomini Library with an individual ticket, which you can buy here. To see any other building of the Duomo Complex, you’ll need the Opa Si Pass, which includes all of the sites. The Gate of Heaven tour is an add-on to the Opa Si Pass (prices and booking on the official website).
Queues at the ticket office can be long, so book ahead (essential if you want the Gate of Heaven).
Getting to Siena
Regional trains connect Siena to Florence and Poggibonsi-San Gimignano (for San Gimignano). Prices are fixed, so there’s no need to book ahead.
Siena’s train station is two kilometres downhill from the historic centre. From the shopping mall opposite the station exit, escalators carry you most of the way up, leaving a 15 to 20 minute walk to the centre.
Buses are often easier. Services from Florence run frequently and stop at Piazza Gramsci or Via Tozzi, close to the historic centre.
My favourite restaurants
Both of these were recommended by my guesthouse hosts, and both delivered.
This historic restaurant serves inexpensive, homely food. There’s no menu as such, but a board with the day’s specials and the staff will guide you through the choices.
Prètto Prosciutteria e Convivio
A friendly spot for platters of local meats and cheeses, and a good choice for a lunchtime sandwich too.
Where to stay
I enjoyed my stay at Antica Residenza Cicogna, a guesthouse in the heart of Siena. It was full of character, and the rate included a superb breakfast. The owners were friendly and helpful, and I loved the shared lounge where you could relax with a hot drink.
If that’s not quite right for you:
B&B Le Logge Luxury Rooms has some of the best room views in Siena. One even has a sauna.
Palazzetto Rosso is a 3-star hotel inside a 13th-century palace in the historic centre, with stellar reviews and panoramic views from its pricier rooms.
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Plan Your Trip to Tuscany
That’s my guide to Siena. I hope it helps you plan your visit; it is a special place.
If you’re exploring more of Tuscany, here are a few guides that might help:
FLORENCE: Plan your solo trip to Florence or discover how to spend three days in Florence. Alternatively, tailor-make your itinerary from my must-see sights in Florence and art guides, including Michelangelo’s artistic masterpieces in Florence and the paintings in the Uffizi Galleries.
Need somewhere to stay? Here’s my Florence accommodation guide.
TUSCANY: Narrow down your road trip choices with these gorgeous towns in Tuscany.
Buon viaggio!
About Bridget
Bridget Coleman has been a passionate traveller for more than 30 years. She has visited 70+ countries, most as a solo traveller.
Articles on this site reflect her first-hand experiences.
To get in touch, email her at hello@theflashpacker.net or follow her on social media.