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Travel bucket list idea:

Last updated: 27 March, 2024
Expert travel writer: Nicky Swallow

According to many of its citizens, Siena is the most perfect medieval city in the world. A glorious ensemble of red brick buildings and exquisite monuments, it’s famous for its fan-shaped Campo and the twice-yearly Il Palio horse race.

Any visit to the city should begin in the sloping Piazza del Campo, the city’s main square, fringed with cafes that are perfect for a doppio espresso and a spot of people-watching. The square is dominated by the Mangia Tower and the Palazzo Pubblico – and climbing the tower is a great way to start your visit, giving wraparound views of the city and surrounding countryside.

The old town is relatively compact and the best way to explore is simply by strolling through the ancient streets and alleyways.

While you’re there

Art lovers should dip into the Civic Museum (Museo Civico) for its dazzling array of paintings by Lorenzetti, Simone Martini and other Sienese masters. There’s another fabulous collection in the National Art Gallery (Pinacoteca).

The ex-hospital of Santa Maria della Scala is another must-see for its brilliant archaeological museum and frescoed Pilgrim’s Hall. The Gothic, zebra-striped Duomo houses a celebrated polychrome floor; usually covered for protection, it’s normally visible in August and September.

Siena is famous for its sweet delicacies; almondy ricciarelli biscuits, aniseed-flavoured cavallucci and the solid, dried fruit-based panforte. One of the best places to sample them is the Antica Drogheria Manganelli in Via di Citta 71-73.

Recommendations

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Civic Museum of Siena

Siena, Tuscany, Italy

exterior of the The Pubblico Palace in Siena

A must-see for its collection of paintings by Lorenzetti, Simone Martini and other Sienese masters. One of the highlights is Simone Martini’s Maesta fresco (1315); another is Lorenzetti’s fresco cycle The Allegory of Good and The Effects of Bad Government (1338-40).

Adult price: £8

Best for ages 18+

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National Pinacoteca Siena

Siena, Tuscany, Italy

Pinacoteca Nazionale exterior entrance door

A 15th-century palazzo housing more than 1,500 artworks, one of Italy’s foremost collections includes an array of dazzling Sienese fondi d’oro paintings (with gilded backgrounds). Expect works by Guido da Siena, Lorenzetti, Sodoma and Beccafumi.

Adult price: £7

Best for ages 18+

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Santa Maria della Scala

Siena, Tuscany, Italy

Santa Maria della Scala

This ex-hospital building was founded in the 9th century (making it one of Europe’s oldest), and only closed relatively recently; the author Italo Calvino died here in 1985. It houses an excellent archaeological museum and the wonderful ‘Pilgrim’s Hall’ decorated with 15th-century frescoes depicting the history of the hospital.

Adult price: £8

Best for ages 18+

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Siena Cathedral

Siena, Tuscany, Italy

The facade of the Siena Cathedral in the sunlight and the circular window

The magnificent Gothic, zebra-striped Duomo houses a celebrated polychrome floor, often covered for protection but normally visible in August and September. Look out for Nicola Pisano’s superb marble pulpit and the young Michelangelo’s Piccolomini altar.

Best for ages 18+

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Siena Market

Siena, Tuscany, Italy

Siena Market

Siena’s principal market, held each Wednesday morning, is one of the best in Tuscany. Stalls are set up at La Lizza, filling the streets around the Fortezza. Apart from excellent produce (cheeses, charcuterie, olive oil and wines, fruit and vegetables), you’ll find clothing, shoes, bags and household items.

Best for ages 13+

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Osteria Le Logge

Siena, Tuscany, Italy

Osteria Le Logge

Located a minute’s walk from Piazza del Campo and occupying a former grocer’s shop with a retro vibe, Le Logge is a classic osteria. They offer a creative take on regional dishes such as tagliatelle with Tuscan ragu, stuffed rabbit with blueberries, black garlic and fermented carrot and braised beef cheek.

Adult price: £30

Best for ages 18+

Duration: -

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Pasticceria Nannini

Siena, Tuscany, Italy

Pasticceria Nannini

A historic cafe and pastry shop that’s been around for almost a century. It’s a great place to sample and buy panforte (the dense, flat cake made with nuts, dried fruit, spices and honey) and light, almond-y Ricciarelli biscuits.

Best for ages 4+

Duration: -

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Logistics

Price: Free
Minimum age: Any
Age suitable: 18+
When: All year around

Getting there & doing it

Siena lies around 70km south of Florence, down the toll-free superstrada. Parking is forbidden in the city centre but there are large car parks around the edge. There are good bus and train links; the train station is 1.5km from the city centre, but there is a frequent bus service. The bus station is closer in Piazza San Domenico.

Wandering on foot is the best way to discover the secrets of the Palio; keep your eyes open for the little ceramic plaques with symbols of the 17 contrade (districts) on street corners and buildings.

The main tourist office is in Piazza del Campo; they have details of tours in and around the city plus maps and information brochures.

When to do it

Unless you specifically want to see the Palio, avoid visiting around the two annual race dates, July 2nd and August 16th, when the worst of the crowds jostling along the streets close to Piazza del Campo.

May to September is always extremely crowded. Winter is a wonderful time to visit, but if that’s not possible try and make an early morning start.

Who to go with: organised tours

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Our selection of the best Viator tours of this attraction or activity

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Florence

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence.

Price: €85

Min age: 0

Rating 4.82 / 5 [14143 ratings]

Tour supplied by:

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Florence

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing
There’s more to Tuscany than Florence. Leave the city behind and discover three other enchanting Tuscan destinations on this day trip to Siena, San Gimignano and Pisa. Take a guided tour of beautiful Siena, famous for its bareback horse race and the Gothic Siena Cathedral, and taste typical Tuscan food and wine during a 3-course lunch in a local winery or restaurant surrounded by picture-postcard Tuscan landscapes, where vineyards, rolling hills and olive groves will be your travel companions. Then, enjoy free time to explore San Gimignano, a picturesque medieval village, and Pisa, home to the UNESCO-listed Leaning Tower of Pisa.

Price: €65

Min age: 0

Rating 4.36 / 5 [3144 ratings]

Tour supplied by:

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

Florence

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Discover the timeless allure of Tuscany on an immersive full-day journey! Step into the enchanting past of San Gimignano, often dubbed the "Manhattan of the Middle Ages" for its towering skyline. Traverse its cobblestone streets, steeped in history, and soak in the panoramic views of this captivating Tuscan hill village. Next, delve into the cultural richness of Siena as your expert guide unveils its treasures during a comprehensive tour of the spellbinding old town. Immerse yourself in the traditions and heritage that make Siena an icon of Italy. Explore the quaint Monteriggioni Hamlet (*). Then, prepare your senses for a typical Tuscan lunch, while savoring exquisite wines, each sip telling a tale of the region’s rich viticulture, a perfect finale to your day in Tuscany's heart. Please note that the order of the visits may change (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Price: €67

Min age: 0

Rating 4.19 / 5 [2449 ratings]

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Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Florence

Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

Price: €55

Min age: 0

Rating 4.37 / 5 [1056 ratings]

Tour supplied by:

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Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Florence

Siena and San Gimignano: Small-Group Tour with Lunch from Florence
Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable and relaxed way with more personalized attention of a small group. Depart from Florence, see the highlights of Siena through the eyes of a licensed guide, admire the marvelous Tuscan landscape, taste genuine Tuscan food paired with great wines, and finish your day relaxing in the hill top village of San Gimignano.

Price: €149

Min age: 4

Rating 4.91 / 5 [1011 ratings]

Tour supplied by:

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Destination guides

2

Destination guides including or relevant to this experience

Florence

Tuscany, Italy

Florence

A heady mix of incomparable Renaissance art, gorgeous palazzos, Tuscan cuisine and home-grown haute couture.

Tuscany

Tuscany, Italy

Tuscany

The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.