Arguably the most beautiful city in Tuscany, Siena has sensational food and one of the world’s most eccentric festivals.
What is Siena all about?
It’s hard to rein in the giddiness walking through Siena’s winding hilltop streets. The walls climb high, the decoration leaps out from all angles and every shop seems to be selling things you want to snaffle or scoff.
Long Florence’s Tuscan power rival, Siena does things subtly differently to its northern competition. For a start, the architecture and the art tend to the Gothic rather than the Renaissance. And there’s an element of hyperlocalisation, too, with the 17 contrade (city wards) all determined to add their own character. This generally means decking the streets in their own flags, and painting the streetlamps in their own colours – but it turns into fierce partisanship and street parties when the Palio horse race comes round twice a year.
At other times, though, it’s best to let go of the reins and whole-heartedly embrace that giddiness. Siena is both staggeringly beautiful and packed with treasures worth nosying into.
A walk through Siena’s highlights
The city’s heart is Piazza del Campo, the weirdly sloping main square, with mismatched but pretty buildings around it and the gigantic red brick Palazzo Pubblico hogging the limelight. It was built for Republic of Siena’s government in the 13th century, and is now home to the Museo Civico. The humungous frescos and paintings inside are unusual in that most were commissioned by the city authorities rather than the church. Hence, a wider range of topics and types of people featured than usually featured elsewhere in Tuscany.
This also applies to the Pilgrim’s Hall – the highlight of the Complesso Museale Santa Maria della Scala, which was a former hospital. The fresco cycles depicting the building and work of the hospital are tremendously vivid, and there’s not a Madonna and child in sight.
The neighbouring cathedral has more predictable artistic themes in its crypt and baptistry, but the cathedral itself is an astonishing piece of lightly Gothic architecture. The columns of black and white marble inside will make you feel like you’re walking through a field of giant zebra legs.
The incredible Palio festival
The biggest days of the year in Siena are July 2 and August 16, when the world’s craziest horse race takes place. Bareback jockeys representing the contrade hurtle around Piazza del Campo at frankly dangerous speeds, as thousands of people cram into the middle to watch. But it’s more than a race – it’s a city-wide fiesta full of pageantry and tradition.
Siena tours and experiences
Tour and experience options in Siena include skip-the-line Duomo and city walking tours, Tuscan cooking classes and wine-tasting in a medieval cave.
Siena restaurant picks
Ristorante San Desiderio is closed to Piazza del Campo, but feels well-hidden down a side street. It does a marvellously tender sliced beef steak with rosemary sauce and roasted potatoes, served up in an exposed brick dining room with inexplicable pictures of horses all over the walls.
Ristorante Grotta Santa Caterina da Bagoga goes all in on Tuscan ingredients – cream! Truffles! Cheeses! Beef stews! – with outdoor tables on a hugely atmospheric back street. The set menus are pretty good value.
Shopping in Siena
The main thoroughfare, Via Banchi di Sopra is absolutely crammed with shops, most of which specialise in something a little different. Salmoiraghi & Vigano does sunglasses, for example, while Franchi does leather bags and Imperial has a strong line in wild, colourful women’s jackets. There are also approximately ten zillion food shops selling hunger-inducing meats, breads, pastas and cheeses.
Elsewhere, Siena does a nice line in ceramics shops. Martini Marisa (anticasiena.it) has been handmaking everything from painted tiles to milk jugs since 1979 – and they can custom-make to order, then ship worldwide.
Unlike Florence, where locals have long moved out of the centre, Siena’s heart is a living, breathing place. And that’s why there are so many great food shops – they’re not just relying on tourist trade. The Consorzio Agrario Siena at Via Giuseppe Pianigiani, 9 is a mouthwatering example of somewhere you can bump into the Sienese stocking up on top drawer, locally grown groceries, while accumulating a mighty fine picnic yourself.
Siena accommodation recommendations
The five star Grand Hotel Continental, a converted 17th century palace, is in a brilliant position in the heart of the city. The classic doubles go for four poster beds and possibly overly floral old school elegance.
Pensione Palazzo Ravizza is an absolute charmer, with a little bookshop downstairs, and a lounge with a piano and an old-fashioned record player upstairs. But the real star is the fantastic, fountain-centred garden with a terrace overlooking the Tuscan hills.
For a good all-rounder, the NH Siena has undergone a recent renovation and is about ten minutes’ walk from Piazza del Campo. Go for the upper floors for better views.
There are strict rules about bringing cars into the heart of the city, and authorisation has to be applied for in advance. If coming by car (and it’s best not to), then sort this out with your hotel before arrival.
Disclosure: This story contains affiliate links. If you book through them, I get a small commission.
