A perfect day in Siena

San Domenico Church is one of the best places in Siena to watch the sunset. Photo: Shutterstock

Home to an intricate history, mesmerising architecture and local delicacies that will make your stomach rumble simply at the thought, you’d be foolish to miss Siena; here’s how to spend a perfect day in the city

9.00am: Piazza del Campo 

All roads lead to Il Campo, the city’s huge main, central square. Here, you’ll find a hub of activity and iconic Sienese sites. Take a seat at one of the many outdoor restaurants (our favourite is Al Mangia) and people watch while sipping your morning cappuccino. From here, you can see the Fonte Gaia, the square’s delicate fountain, which hides a network of secretive tunnels below. 

At the square’s base is the Palazzo Pubblico, the dignified Town Hall with its crenellated façade and waving banners, surmounted by the tall and slender tower. Make time to climb the 500-steps of the Torre del Mangia, while you’re here. You’ll find glorious views over the grand piazza and Siena’s rooftops from the top. 

10.00am: Marvel at the marble cathedral 

The Duomo is Siena’s most controversial monument: seen as a symphony of black-and-white architecture or a tasteless striped tower, depending on your view. It began in 1220 as a round-arched Romanesque church but soon acquired a Gothic façade festooned with pinnacles. A second massive structure was planned in the 14th century. However, construction was halted during the time of the plague and never resumed. The half-finished structures can be seen from the outside. Take a guided tour on a trip to the city with Insight Guides: submit a trip request today and our local experts will teach you all there is to know about the city's in-depth (and often complicated!) history. 

Inside, the cathedral is just as impressive. Oriental abstraction, Byzantine formality, Gothic flight and Romanesque austerity combine in a mishmash of styles to create one of Italy’s most stunning and unique interiors. Look up and you’ll notice a giddy chiaroscuro effect created by the zebra-striped walls reaching up to the starry-blue vaults. 

Aerial view over Siena vshowing the black-and-white striped cathedral. Photo: Shutterstock

11.00am: Explore centuries of history 

Opposite the cathedral on the piazza, Santa Maria della Scala is often described as a city within a city. It began life as a hospital a thousand years ago and continued as one until its reincarnation as a museum in the year 2000. Having hosted a pilgrims’ hostel, poorhouse, orphanage and hospital, the site is rich with history, especially now its walls contain some of the city’s most impressive artworks. You’ll find a sprawling museum complex here (two hours is just enough time for the highlights), home to frescoed churches, an archaeological museum, and major medieval and Renaissance art exhibitions. 

1.00pm: Lunch like a local

Head to Orto de' Pecci for hearty Italian food with few tourists in sight. This restaurant is a hidden highlight in a city packed with pizzerias and pasta-laden menus. Found in one of the centre’s few green spaces, the restaurant is surrounded by greenery and is even home to a donkey. The menu changes with the seasons so you’ll find a fresh, unique offering here. Classics will always remain on the menu, however, including the pici – shoe-lace thick spaghetti, which is a Sienese speciality – with basil-laden tomato sauce or pesto. 

Plenty of outdoor restaurants will ensure you make the most of Siena's often sunny weather. Photo: Shutterstock

2.00pm: Discover the city’s secret Contrada

Siena is home to 17 distinct districts each with its own symbol, colours, flag, church and even rival, with traditions dating back to medieval times. As you tour the city’s streets, you’ll notice each district clearly displays affection for its Contrada, with flags, small signs and lamps scattered around. 

See if you can tick off all 17 icons throughout your day: caterpillar, dragon, eagle, forest, giraffe, goose, owl, panther, porcupine, ram, shell, snail, tortoise, tower, unicorn, wave and wolf. Phew!

Our local experts will guide you through the city, helping you on this treasure hunt! Simply include a guided tour of Siena on your itinerary: talk to a local expert today to get your trip itinerary started. 

3.00pm: Sample a mid-afternoon pick-me-up

Nanini’s is a Sienese institution. Arguably home to the city’s best, richest coffee, pop in late afternoon for a little pick-me-up. Order at the bar over the gaggle of gossiping locals, and simply shot your espresso or take a longer drink to go. Stop by traditional bakery Il Magnifico for sweet, light, melt-in-your-mouth Sienese biscuits known as ricciarelli. Made from almonds and dusted with a sprinkling of sugar to finish, they offer the perfect accompaniment to your afternoon caffeine hit.

4.00pm: Gaze at beautiful gardens

Reenergised, head to see Siena’s outdoor spaces: make your way south to the Orto Botanico, a pretty botanical garden just inside the city walls. Opposite the Orto Tolomei is another little garden with a lovely view over the Tuscan countryside and a sculpture that – although not obvious at first glance – outlines the shape of the city. 

5.00pm: Savour a glass (or two) of the good stuff

Enoteca Italiana stocks some of Italy’s greatest wines. Here you'll find both a wine exhibition and shop, where you can take part in guided wine tastings from a wide range of Tuscany’s finest. This is also the best place to study and savour Sienese wines, from Chianti Classico to Vino Nobile di Montepulciano, Brunello di Montalcino and Vernaccia di San Gimignano. 

Tasting a wide range of Tuscany’s wine is the best way to while away your time in the early evening. Photo: Shutterstock

6.00pm: Watch the sunset behind the Basilica de San Domenico

This huge fortress-like church is a great spot to watch the evening’s sun turn Siena’s rooftops from typical terracotta to fiery shades of orange, brown and red. Inside, the chapel is decorated with frescoes dating back to the early 16th century. But, outside, the view across to the striped black-and-white Duomo is spectacular. 

8.00pm: Dine alongside the city’s contrada

Siena is a city spread out over a number of rolling hills, this means the streets are sloped, steep in places and often awkward. Grotta di Santa Caterina, tucked away on a little backstreet, has tiny rows of small, straight platforms for diners to eat outside on. Aside from this quaint addition, the Italian food and history here is unmissable. The restaurant pays homage to each of the Contrada, with decorated plates and other memorabilia on display.

Tuck into traditional Tuscan cuisine from the menu, often with a modern twist attached. Think wild boar pappardelle or picis porcini. 

10.00pm: Leave room for dessert

To finish, head back to Il Campo for a final tour of the square lit-up at night: it takes on a completely different atmosphere. Once you’ve worked up an appetite (again!), you’ll find to the left of Palazzo Publico, Gelateria Caribia offers a multitude of ice cream flavours. They work to constantly produce new, exciting and unique flavours for visitors to taste, including combinations like Nutella and coffee or luxurious Bellini. Be warned, the portions are generous. 

Ready to take a trip to Siena? 

Let Insight Guides’ local experts create your ideal itinerary from start to finish: submit a trip request today