Siena's Duomo is zebra-striped and a main attraction for visitors (Fred Caws)
Article Words : Daisy Cropper | 28 December

Short break in Siena, Italy

Last year you, Wanderlust readers, voted Siena the best city in Europe. Amid medieval streets, towering houses and chianti wines, Daisy Cropper finds out why

Where? Tuscany, central Italy
Why? Fascinating history, truly mesmerising art, tempting cuisine
When? May/June or Sept/Oct: nice weather, fewer people

Siena is a city at war. A war in which porcupines and wolves are rivals; where snails often reign and unicorns lag behind. Like a fairytale, the city’s history is a riotous affair. In Siena, a unique set of clans – known as contrada – still rules the streets. The city is divided into 17 districts, each decorated with the symbols of their mascots, which fosters tight-knit communities.

In reality, there’s no bloodshed, and the rivalries between contrade come to little more than boisterous banter at Il Palio – Siena’s world-famous horse races. The annual event sees ten stallions (there’s not room for all 17; lots are drawn) charge around the city’s grand Il Campo square three times, on two separate occasions, in a heart-pounding race for the crown.

The Palio sees Siena overrun every July and August. Yet, although often bypassed by tourists in favour of Florence’s frescoes and Pisa’s wobbling, the city is worth visiting every month of the year. It is bursting with beautiful buildings, fascinating art and belly-bulging cuisine. 

Originally established by the Etruscans, and refounded as a Roman colony in the first century BC, it was in the 14th century when it became one of the most prosperous hubs in Italy, often battling nearby Florence for commercial and cultural supremacy. Then the plague hit in 1348: two-thirds of the city’s population was lost.

A period of decline followed – which may have been the saviour of the medieval gem we see today.

Therein lies Siena’s main attraction: its excellent preservation. Plus it trumps other Italian cities with its friendlier feel and smaller size – ten times smaller than Florence, it’s easier to immerse yourself here and experience real Sienese life.

Nestled over seven sharp hills, the centre is a maze of narrow streets where every corner and every crest brings something new, interesting and exciting to discover. And, perfect for burning off all that spaghetti, everything here is done on foot.

The city centre was pedestrianised in 1966: there are no blaring horns or exhaust fumes, which simply increases the city’s charm. It’s a fantastic alternative city break. In the centre you can find your fill of art and culture, but it’s also easy to zoom off into the countryside on an Italian scooter for exploring, hiking and wine-tasting. Which is exactly what I did, camping in the Tuscan wilds, stumbling upon hilltop towns and generally eating my way around the region before returning to Siena for a fine finale.

Wanderlust readers voted Siena their favourite European city in last year’s Travel Awards. After my stay here, it certanly gets my vote.

Siena day by day

Discover ancient art and culinary delights before exploring the Tuscan countryside

Essential info

When to go: In spring and autumn the weather is glorious and crowds smaller. Visit in July-August for Il Palio – but be warned, hotels get booked up months in advance.
Getting there: Fly to Pisa. easyJet and Ryanair both fly to Pisa from a range of UK airports; flight time is 2.5hrs. Take the train from Pisa to Siena, changing at Empoli; journey time is around two hours. Siena’s train station is 2km from the centre; buses leave from the station and take around ten minutes.
Getting around: Vehicles are banned in the city centre – only motorcycles and mopeds are allowed. Pull on comfy shoes and explore the city on foot.
Where to stay: Hotel Alma Domus (doubles from €75) is central, cosy and welcoming; third-floor rooms have impressive views of Siena’s Duomo, the red-roofed cityscape and Tuscan hills.
Where to eat: There is a tempting wealth of restaurants, bars, cafés, gelaterias and pasticcerias to gorge in. See Day 2 (below) for specifics.
Further info: Tuscany & Umbria (Rough Guides, 2012) provides detailed information on the city’s main sites, as well as advice on the nearby countryside. Also try Footprint Focus Siena & Southern Tuscany (Footprint, 2012).
10 things to do for free in Siena; Top 5 Tuscan hill towns; and 7 Sienese recipes for more information and inspiration.

Tickets please!

Various combo tickets are available. A Civic Museum Authorities two-day pass covers the Museo Civico, Santa Maria della Scala and the Palazzo delle Papesse for €11.

Look for...

Siena’s 17 contrade symbols: caterpillar, owl, dragon, eagle, forest, giraffe, goose,  panther, porcupine, ram, shell, snail, tortoise, tower, unicorn, wave, wolf.

Day 1: Medieval marvels

There are plenty of ancient monasteries, cathedrals and even hospitals to visit. Make your first stop the Duomo: Siena’s cathedral is an awe-inspiring example of 13th century Gothic architecture, with an interior equally magnificent (don’t miss the Michelangelo sculptures). The zebra-striped walls will leave your head spinning, as will the meanings behind the centuries-old frescoes.

Stop by the Santa Maria della Scala, previously the city’s hospital, and now a museum housing a wealth of art. It is also home to the fascinating Museo Archeologico, which is full of Roman artefacts.

While roaming Il Campo – Siena’s grand main square – visit the Museo Civico, housed in the Palazzo Pubblico. Here, the intricate works of art include Lorenzetti’s The Allegory of Good and Bad Government – one wall painting depicts peace, faith and hope (Siena); the other fear, sin and evil (Florence, according to our local guide). Climb up the adjacent 87m-high Torre del Mangia for unbeatable views over the city and out to the Tuscan countryside.

Next, grab an afternoon pick-me-up and savour Siena’s best coffee: Nannini (Conca d’Oro, Banchi di Sopra 24) is where locals head for a caffeine kick. Knock back an espresso at the bar or relax with a latte and a pastry (or two).

In the evening, walk through the city’s quieter streets (crowds tend to disperse later in the day) to San Domenico, an imposing 13th-century church and resting place of the head of St Catherine, Italy’s patron saint.

Day 2: Sienese specialities

The Sienese are very proud of their history. You’ll see evidence of this in all aspects of life, even the food. Pop into Il Magnifico bakery for sweet melt-in-your-mouth ricciarellis – a Sienese biscuit with medieval origins, made from almonds, sugar and eggs.

Take a guided tour (ritaceccarelli.it) to learn the city’s darkest secrets. Or follow a self-guided walking trail around the city walls – hotels will have maps; it takes around three hours.

Stop for lunch at Orto de Pecci (Via di Porta Giustizia 39), which serves hearty Italian food with no tourists in sight. The restaurant is set in a tiny green space in the midst of the city – it was once where the condemned were hung; since the 16th century it’s been used as a kitchen garden. Try the pici with tomato sauce or pesto – this thick, wormy spaghetti is a Sienese speciality.

One of the city’s greatest secrets lies beneath its surface. Between the 13th and 15th centuries, medieval engineers hand-carved 25km of narrow tunnels – known locally as the Bottini – to direct and safeguard the city’s water system.

You can see overground evidence of their impressive handiwork at the Fontebranda (down the hill from San Domenico), one of three medieval fountains still standing; locals say its water is still pure enough to drink.

Tours of the underground tunnels can be arranged in spring and autumn. Contact Associazione La Diana (www.ladianasiena.it – in Italian) for more information.

Day 3: Get on your bike!

Take to the Tuscan countryside for a glimpse of the surrounding hills, olive groves and vineyards. Make for the town of Gaiole in Chianti (40mins north by bus; singles around £2) to pick up a Vespa from the tourist office on the main square (from €40 per day; www.tuscanyscooterrental.com).

Drive 30 minutes north-west  through typical Tuscan countryside to Radda in Chianti. Vespas are permitted in the town’s centre, so you can scoot through tiny alleys and backstreets to discover its charm.

Continue westwards along small, traffic-free roads to the hill-top town of San Gimignano, via Castellina in Chianti and Poggibonsi. Cruise past rolling hills, endless vineyards and fields of canary-yellow sunflowers.

Awarded UNESCO World Heritage status for its medieval centre, San Gimignano offers the Tuscany first-timer the perfect introduction. Fourteen striking towers loom over the city (originally there were 72); climb the 54m-high Torres Grossa for panoramic views.

Walk along the city walls and stop at Ristorante La Mangiatoia (Via Mainardi 5) for sweet bruschettas and creamy desserts. Or try the restaurant of Hotel Bel Soggiorno (Via San Giovanni 91) for Tuscan food and views through huge windows to the countryside beyond.

As Wanderlust's Assistant Website Editor you'll find Daisy working on anything and everything across the Wanderlust website, including writing news, producing features, proofing and subbing content, organising competitions, interacting with myWanderlust and more.

When she can peel herself away from the world of the web you'll have a hard job finding her: the self-confessed travel nut has admitted she wants to visit all the countries in the world... And so far, she's only been to 14.

Follow her adventures on Twitter: @daisy_cropper