Wanderlust readers voted Siena their favourite European city in last year’s Travel Awards and it’s not hard to see why. Daisy Cropper explains how to stay on budget in one of Europe’s most magical cities
Mythical stories surround the founding of Siena – according to the town’s legends the city was first settled by Senius, nephew of Romulus, whom Rome is named after. On a more official note, Siena’s origins date back to the first century AD and there is evidence of this ancient history all over the city.
Walk along the main street, Via Dei Montanini which leads to Banci Di Sopra and eventually connecting to the Piazza del Campo. Here you’ll discover Roman evidence in the building’s structures, materials and even in inscriptions. Look out for dappled red bricks – where small crimson stones are mixed with cement – this is a Roman construction technique used centuries ago.
Small square-shaped holes can also be seen on many of the city's buildings – known as buche pontaie – this is where medieval workers would have fixed wooden poles to hold scaffolding during construction.
Each of Siena’s 17 districts has its own symbol, colours, flag, church, and even a rival, forming traditions which date back to medieval times. These clans are known as Contrada and make up the foundations of the city’s unique, community-led and relaxed way of life.
Each district is adorned with adoration for its Contrada. Streets are lined with flags, small signs, lamps and more. See if you can discover all 17 symbols on a self-guided walk of the city.
Tick them off as you find them: caterpillar, dragon, eagle, forest, giraffe, goose, owl, panther, porcupine, ram, shell, snail, tortoise, tower, unicorn, wave and wolf.
If you're lucky, in the evening you may be treated to the sight of small parades or flag-waving crowds and hear drums beating. The Contrada often practise for their annual parades at the Palio (see number 9 below).
Siena’s past has been colourful to say the least. Fighting battles against Florence and armies from further afield (including the English) has left the city scarred and rebuilt time and time again. Different rulers had different styles, which are reflected in Siena's varied cityscape.
Across the city you'll see square-shaped Guelphic merlons or battlements. Although, beady-eyed visitors will be able to spot the well-hidden Ghibelline battlements – shaped like a swallow's tail – tucked away amid the red-roofed houses. This curved design was a favourite of Florentine rulers.
It's easy to spot the imposters at the top of the Torre del Mangia (entrance in the Palazzo Pubblico) – although there's a steep entry fee (€8-13) and over 400 steps to navigate.
Siena is surrounded by ancient walls, which once kept the residents safe from approaching armies. More or less, you can walk around the entire city just by following these periphery walls. Now and then a private garden, medieval convent or houses will block your way but you will easily slip through a narrow street and find yourself following the ancient walk ways once again.
The entire walk takes around three hours and you will see real city life on the streets away from the hordes of tourists.
There are so many art-filled galleries, museums and fascinating buildings to explore in Siena you'll soon wear your feet out. For a free museum head for the Archivio di Stato – home to the city's detailed and lengthy archives.
Bundles of centuries-old documents live here with unread details of the city's long-lost way of life. Take a look at the chief exhibits – the Tavolette – intricately painted wooden panels, which act as covers for the civic records and accounts.
Beginning with religious themes and slowly moving onto scenes from everyday life they provide an insight into six centuries of the city's history.
Well you can’t actually bathe in this fountain but that’s what residents would have done here centuries ago. Located below the San Domenico church the Fontebranda acted as a bathroom for thousands of city dwellers. Locals claim they’d still drink the water here so it’s a refreshing stop on a city tour.
Built in 1193 the fountain proved to be an important meeting point for city dwellers – made up from three basins: one for washing, another for extracting water and one for animals – sit back and imagine what city life was like centuries ago.
The fountain also marks a major point on the city's complex network of underground tunnels, which once supplied the entire city with water. The bottini worms its way beneath the city for a staggering 25km – all of which were dug by hand using rudimentary tools hundreds of years ago.
Tucked away around the bustling city are rare pockets of greenery – bushy olive trees and soft green grass make for the perfect place to escape the crowds of summer tourists.
For a place with a difference make for Piazza del Mercato – just behind the Museo Civico and main Piazza del Campo. You'll see the greenery of Orto dei Pecci from here. Head around the tortoise-shell market place – which used to host livestock sales – and towards a track to the left.
Centuries ago, this was the walk condemned criminals would have made towards their place of execution. Down the tiny track, through the greenery and onto their death. Pretty grim.
On a brighter note, since the 16th century the land has been cultivated with kitchen gardens and open to the public. Scour the greenery for medieval medicinal herbs and keep an ear out for the resident dwarf donkey.
The track also leads to All'Orto dei Pecci – a restaurant serving simple, local Italian food. Push the boat out and stop for lunch: fresh tomatoes used on the bruschetta are grown in the back-garden and the super-thick spaghetti (known as pici) may look worm-like, but is a wholesome Sienese speciality.
This impressive Gothic structure stands tall on one of the city's hill tops. Dominican monks first founded their monastery in 1125, with construction on the church beginning in 1226. As well as free entry to the church, there is also a treasury of art work and frescos to explore, and tip-top views of Siena outside.
In addition to the powerful fresco of St Catherine, which is the only portrait of the Patron Saint painted while she was alive, there is also the Relic of St Catherine's head displayed in the side chapel of the church.
Head for the church in the early evening – sunsets aren't viewable from here but cast a bewitching orange glow across the city's rooftops and cathedral. The crowds tend to disperse around this time too.
An annual event which is sure to get your heart racing – il palio is celebrated twice a year on 2 July and 16 August. Dubbed Italy's most spectacular festival, it is essentially a bareback horse race, where riders circle the main Piazza del Campo three frantic times.
There are 17 competitors – one for each of the city's Contrada – and the race has unique importance to each and every one of them.
Top viewing spots around the square can charge up to €300. Join in with the locals and witness the race from the ground in a huddle in the Piazza for free.
Local tour guide Rita Ceccarelli says the atmosphere is electric and you literally move with the crowd. Rivalries between Contradas break out during the race – members of porcupine and wolf clans do not speak to each other in the race's build up.
Via Giovanni Dupre is the local's favourite entrance to the Piazza on race day. Travellers fearful of big crowds or small places should steer clear of the packed out event – the crowds are BIG.
Italy, and in particular Tuscany, is world-famous for its wine. Where better to explore the intricacies of this region's specialty than in an exhibition housing more than 1,600 bottles?
Entocea Italiana is home to wines from across the country and visitors can explore the wide range on offer, and try a glass or two (for a fee).
For wine-lovers this exhibition reflects both big businesses and tiny vine-yards, painting a balanced view of the country's complex wine industry. Housed inside the bastions of the 16th century Medici Fortress, with grand arches and elaborate features, it makes for an interesting setting too.
Entocea Italiana is on the Fortezza di Santa Barbara – close to the city's main bus station.