You may think of it as that ‘other’ city in Tuscany – the one that’s not Florence. You may plan to visit ‘if’ you have time, once you’ve trod through the museums of Florence, traipsed through the ruins of Rome and plied the canals of Venice by gondola. But a weekend, or even longer, in Siena – the city in Tuscany that isn’t Florence – reveals a compact, manageable city with a glorious medieval centre, winding narrow streets and alleys, and a fascinating history. In Siena, more so than in bigger, bolder Florence, it’s much easier to scratch beneath the surface of brick, marble and wood beam, and discover the heart of one of Italy’s most beautiful and interesting small cities.

Once divided by a bitter, bloody rivalry, Siena and Florence are today separated by only 43 odd miles, and a few centuries. While Florence won the war and wore the crown of the Italian Renaissance, Siena saw its fortunes peak earlier, in the 1200s to 1300s, when it was a centre of banking, trade, learning and the arts. After the Black Plague decimated the population of the Republic of Siena in 1348, the clocks seem to have almost stopped here, to the point that were a Sienese of the 14th century transported to modern Siena, he would still recognize its piazzas, streets and churches and, very likely, be able to find his way home. That’s how little has changed in Tuscany’s ‘second city’, and that’s what enchants first-time and returning visitors.

Duomo of Siena.

Day One: Major sights and a saint’s head

Start a solid day of sightseeing with a proper Italian coffee at Caffè Fiorella (, which brews what is widely regarded as the city’s best espresso. If you need a second breakfast, which Italians typically take around 10am, grab one of their flaky, filled cornetti, or croissants, and wash it down with the contents of your tiny cup.

You’re just one block off Piazza del Campo, most often just referred to as Campo, Siena’s shell-shaped main square. While it’s wise to resist the urge to dine in one of the overpriced restaurants set right on Campo, we’d allow for an overpriced drink or gelato here, if only just to sit and gaze at daily life go past in one of Europe’s grandest public living rooms.

At the bottom of the slanted piazza, you’ll find the imposing Palazzo Pubblico and Torre del Mangia, both worth a visit ( The palazzo has functioned as Siena’s town hall since the 1200s, and its civic museum houses a fresco cycle you may recognize from art history class: Ambrogio Lorenzetti’s Allegory and Effects of Good and Bad Government. Fascinating not just for their look at medieval city and country life, the frescoes represent an important moment in medieval history – the recognition that a responsible, well-functioning government was essential for a healthy, peaceful, productive populace.

Those with hearty lungs and knees should make the climb to the top of the Torre del Mangia, to be rewarded with spectacular views of the Sienese countryside, as well as a bird’s eye view of the layout of the ‘centro storico’, or historic centre.

Museo Civico.

Take your leave of the Campo for now and wind your way up to blocky, gothic Basilica Cateriniana San Domenico (, famous as a veneration site for Saint Catherine of Siena, a nun and mystic of the Dominican Order. Though most of St. Catherine is buried in Rome, where she died in 1380, the possessive Sienese sought to bring at least part of their favourite daughter back to the city of her birth, and smuggled her severed head out of Rome a few years after her death. The mummified head now has its own altar in San Domenico.

Now that you’re away from touristy Campo, find a rustic tavern or ‘enogastronimia’ – a fancy word for a place that sells wine and charcuterie to eat in or to go – and settle in for an easy lunch of local cheeses, cured meats and bread. We like Toscana Golosa ( – which translates as ‘the greedy Tuscan’ – but there are a number of good, reasonably priced places to eat in this area.

Spend the afternoon on a scavenger hunt of sorts, by counting how many ‘contrade’ you pass through. Contrade are Siena’s ancient wards, and ten of the city’s 17 contrade send a horse and rider to the famous Palio bareback horse race on the Campo. Each ward has its own symbol, most frequently an animal, and a fun way to see which contrade you’re in is to look for the fanciful street lamps depicting that ward’s colours, flag and symbol.

Make your first dinner in Siena a special one, by reserving in advance at La Taverna di San Giuseppe (, a very highly rated restaurant that lives up to its hype. You will spend a lot of money to dine here, so go for the full monty of antipasto, pasta course (primo piatto), meat course (secondo) and dessert (dolce), and enjoy a meal and experience you’ll be talking about for years to come.

Santa Maria Della Scala.

Day Two: The Duomo and medieval medicine

Reserve in advance for a timed entry to the Duomo of Siena (, with its stunning rose marble façade and structure of stripes of green and white striped marble. A combined ticket, called an OPA SI Pass, allows access to all parts of the cathedral interior, including the crypt and baptistery. The cathedral itself is dizzyingly beautiful, a riot of marble, mosaic and sculpture. Amazingly intricate inlaid marble floors once told the stories of the Bible to an illiterate public. Though most are covered up to protect them, at least a few are always on display.

After a few hours exploring every nook and cranny of the Duomo, head across the piazza, OPA SI Pass in hand, to Santa Maria della Scala (, one of Europe’s first hospitals, likely built for pilgrims passing through Siena on their way to Rome. Now a museum, the former hospital contains fascinating displays on the history of early medicine, as well as archaeological collections, religious relics and a 14th-century fresco cycle of the life of the Virgin Mary.

Before your Siena sojourn winds down, be sure to sample ‘ricciarelli’, soft almond cookies dusted in powdered sugar. Try them freshly made at Il Magnifico (, a few blocks off Campo.

Piazza Del Campo.

Need to know

British Airways offers non-stop flights (a little more than 2 hours) from London airports to either Pisa (PSA) or Florence (FLR), both with easy train connections to Siena. Both EasyJet and Ryanair fly into Pisa from a number of UK cities.

Siena is easily reachable by train from anywhere in Italy. The train station is about two kilometres downhill from Siena’s centre, so not really walkable for anyone with luggage. Frequent buses connect the station to the ‘centro’, or you can take a taxi directly to your hotel. If you have a car, ask your hotel in advance where you can park it for the duration of your stay in pedestrian-only Siena.

For a budget stay, Hotel Antica Torre ( offers comfortable rooms in a converted 16th-century tower. Hotel Palazzo Ravizza ( is less than ten minutes’ walk from Piazza del Campo and has a garden with wonderful countryside views. For a splurge, the palatial Grand Hotel Continental ( is Siena’s only five-star property and is rich with every imaginable Old World luxury.


Last edited: 6 January 2020

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