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ISSIMO’s Travel Guide to Siena

December 11, 2025

ISSIMO’s Travel Guide to Siena

Come with us to one of Tuscany’s most beautiful cities

Tuscany has no shortage of stunning destinations. From the ochre-tinted Val D’Orcia to culturally rich Florence, beautiful Pienza – the perfect Renaissance city – and the wine-soaked Chianti valley, anywhere you go in the central Italian region is a haven of art, history and natural splendour. 

Among these countless gems, one in particular is very close to our hearts: Siena. Known for its medieval history, the Palio horse race, and its historic centre – a UNESCO World Heritage site – this Tuscan town captures the heart and soul of Italy at its most evocative. Its winding alleys, striking Gothic Duomo, and the shell-shaped Piazza del Campo create an atmosphere that feels both intimate and grand, lived-in yet timeless, proudly Sienese in every detail.

And as of 2027, Siena will become even more entwined with the Pellicano universe thanks to La Suvera, our next great Tuscan chapter – a storied estate reborn and ready to welcome a new generation of travellers.

If you’re keen to make sense of Siena’s narrow lanes, its rich traditions, and all the beauty this extraordinary town has to offer, we’ve put together a guide to help you explore it like an insider. Ready to dive in? 

SEE

Begin your exploration of Siena in the most natural place: Piazza del Campo. The city’s beating heart – and one of Italy’s most iconic squares – began taking shape in the 12th century. Its distinctive shell form, divided into nine segments in honour of the Nine Lords who governed Siena in the late 1200s, naturally draws you in, inviting you to linger, wander, and imagine the thunder of hooves during the Palio.

Next, make your way to the Duomo, a Gothic masterpiece striped in black and white marble and home to works by Michelangelo, Bernini, and Pisano. Inside, be sure to step into the Piccolomini Library, a jewel box of Renaissance frescoes bursting with colour and narrative. Think you’re done being awe-struck? Not quite.

Just a few steps away rises the Facciatone, the striking unfinished façade of Siena’s ambitious “new” cathedral. Climb the narrow, 131-step staircase to the Panorama del Facciatone, where the city unfurls beneath you — a sea of terracotta rooftops, medieval towers, and rolling Tuscan hills beyond. It’s one of the most breathtaking views in Siena, and absolutely unmissable.

Santa Maria della Scala, another must, is also right here. One of Europe’s oldest hospitals turned cultural hub, it features frescoed halls, chapels, and archaeological treasures that reveal Siena’s deep-rooted spirit of community.

EAT

There are lots of great restaurants in Siena – and, as it goes, also a few tourist traps, so beware! – but we have our favourites to share. Osteria Le Logge, a refined but deeply Sienese kitchen, is one of them. Expect seasonal Tuscan staples with quite a few creative touches, exceptional wines, and an atmosphere that blends history with contemporary charm at this former drogheria (grocery store), complete with its original entrance counter and antique glass-fronted cabinets. 

La Sosta di Violante is classic Siena on a plate: pici al ragù, pollo al mattone and homemade desserts, served in welcoming, informal settings Simple, satisfying, and always lively. 

For the best coffee in town – plus irresistible cantucci for the road, make a beeline for Torrefazione Fiorella, while Siena’s most tantalising pastries are found at Pasticceria Nannini Conca D’Oro, an institution in the city. 

Craving a little aperitivo? Try Gastronomia Morbidi Cocktail Bar, which doubles (triples?) up as a bistrot and gourmet deli shop, or, if you’re into vino, Bottiglieria Salefino, slightly removed from the city centre. It’s stocked with excellent bottles from small producers, as well as a good selection of natural wines. 

And because Siena rewards those who snack well: make space for a panino at Gino Cacino di Angelo. Locals swear by it for good reason: these are exceptional sandwiches – generous, inventive, and packed with the kind of flavour that makes you reconsider everything you thought you knew about a simple sandwich.

PLAY

For a bit of a trill, climb Torre del Mangia, the slender brick tower dominating Piazza del Campo for a sweeping 360° view of Siena’s rooftops and the rolling Tuscan countryside. Go early: the climb is steep, but the payoff is unforgettable.

Afterwards, consider exploring the contrade, aka Siena’s neighbourhoods. Tiny worlds unto themselves, each one has its own emblem, colours and fiercely loyal spirit. Wander through them and you’ll quickly feel the city’s heartbeat. 

Last but not least, visit their museums. Even if you’re not in town for the summer races, they offer a beautifully intimate look at Siena’s soul: banners, costumes, relics and stories that bring centuries of tradition to life.

FUN FACTS

A City Beneath the City

Siena sits atop a hidden web of medieval tunnels, the bottini, once used to channel water into fountains across town. Today, they’re one of its most fascinating secrets.

Title

A Horse Can Win Without Its Rider

At the legendary Palio di Siena, jockeys often fall off mid-race… but the horse keeps going. And yes, a riderless horse can still claim victory. Siena loves the drama.

Title

Gothic by Design

Siena deliberately preserved its unique Gothic architecture as a bold statement against rival Florence. The result? One of Italy’s most breathtakingly coherent medieval cities.

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