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Last updated: 29 June, 2023
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.

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 8+

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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 13+

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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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.

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

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

Siena

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket
Single ticket for 3 hours for the wonders of the Cathedral of Siena, Piccolomini Library, Museum, Panoramic Terrace, Baptistery and Crypt. Amazing experience around the Gothic Town most famous of the world. The ticket will be valid for three consecutive days from first entry.

Price: €19

Min age: 12

Rating 4.40 / 5 [247 ratings]

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Full Day: Wine experience in San Gimignano, Siena & Monteriggioni

Florence

Full Day: Wine experience in San Gimignano, Siena & Monteriggioni
Enjoy a full-day tour visiting Tuscan villages and exploring the Chianti wine region! The village of San Gimignano, the Chianti area, and the medieval town of Siena are situated in the heart of Tuscany. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Meet our staff in Florence and start your amazing journey! The first stop will be San Gimignano, a magnificent example of a Medieval urban town where you will have free time to visit the village and its splendid squares and towers. The tour will continue with the visit to the marvelous Monteriggioni medieval fortress. Don’t miss the chance to walk along the medieval wall or on the famous medieval Francigena Road. Here you will spend your free time before starting your ride to Siena. Enjoy a tasting in the Chianti Area, before coming back to Florence.

Price: €35

Min age: 0

Rating 4.44 / 5 [743 ratings]

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Skip the Line: Siena Duomo and City Walking Tour

Siena

Skip the Line: Siena Duomo and City Walking Tour
Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and visit the stunning Siena Duomo (Siena Cathedral) with your fast-track, skip-the-line entrance ticket. As you walk through this incredibly beautiful Tuscan city with your expert guide, you'll feel as though you’ve journeyed back in time.

Price: €35

Min age: 0

Rating 4.75 / 5 [418 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 4.36 / 5 [1009 ratings]

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Hunt for the 10 Treasures of Siena

Siena

Hunt for the 10 Treasures of Siena
If you are looking for a unique and fun activity to involve the whole family in the interactive discovery of the most hidden but no less fascinating places in Siena, you cannot miss our Treasure Hunt! Furthermore, instant photography will allow you to appreciate the beauties of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Find out all the details, solve the puzzles and answer the quizzes to transform your visit to Siena into a unique memory to share with the whole family, young and old, and with friends. N.B. In the days of the Palio (29 June-2 July and 13-16 August) the treasure hunt route is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.

Price: €56

Min age: 0

Rating 4.96 / 5 [26 ratings]

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Wine Class - Tuscan Classics

Siena

Wine Class - Tuscan Classics
Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and fun class to learn about Tuscany's most important, traditional wines led by an English-speaking local expert. Discover the history and legends behind Tuscany's most significant wines and learn to swirl, smell and sip your way through the different types and styles of wine. The tasting of wines is enhanced by a series of different sample foods, and food pairing tips will be discussed, leaving you able to make better choices when choosing from local names in the city's restaurants.

Price: €60

Min age: 18

Rating 4.94 / 5 [258 ratings]

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Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting

Florence

Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting
Your Highlights of Tuscany discovery begins with Pisa. Where we reach Piazza Miracoli, dominated by the Cathedral, the Baptistery and the Leaning Tower. From Pisa, we drive over the countryside up to San Gimignano, where a traditional Tuscan lunch with the tasting of four different wines, will be served in a characteristic Restaurant, located along the famous "Via Francigena". After lunch time, your visit continues to the discovery of a Tuscan medieval pearl, the stunning village of San Gimignano, Unesco world heritage, known for the ancient town planning still intact. Our last stop is Siena, where our local guide will take you on a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world "Monte dei Paschi", the Piazza del Campo where the famous "Palio" horses race takes place twice a year, to the spectacular Cathedral. Please note that the order of the visits may change

Price: €65

Min age: 0

Rating 4.56 / 5 [444 ratings]

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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
Full day Tour in the heart of Tuscany region: San Gimignano - the "Manhattan of the Middle Ages", the most famous and picturesque Tuscan hill village together with the unique experience of Siena and its traditions, thanks to the comprehensive guided tour of the stunning old town. The picturesque Monteriggioni Hamlet and the relaxing stop at a Chianti Winery for a typical Lunch which includes the guided Tasting of 3 different Wines and “vin santo”. Please note that the order of the visits may change (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Price: €67

Min age: 0

Rating 4.16 / 5 [2320 ratings]

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Wine Tour with Wine Tasting in Siena

Siena

Wine Tour with Wine Tasting in Siena
In the hills of the gorgeous Tuscan countryside,  just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine and Life' is a 3-hour tour held in an organic winery. Learn about the different stages of wine making through the seasons and enjoy tastings and a light lunch.

Price: €75

Min age: 18

Rating 4.98 / 5 [194 ratings]

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Florence Day Trip: Pisa, San Gimignano, and Siena with Lunch

Florence

Florence Day Trip: Pisa, San Gimignano, and Siena with Lunch
Enjoy this full-day trip to Siena, San Gimignano, and Pisa from Florence. Reach easily our meeting point by taking the T1 tram heading to Villa Costanza. Immerse yourself in the rich tapestry of Tuscany's history as you explore the three most iconic cities of the region. Discover the timeless wonder of the majestic Square of Miracles, where historical architecture and enchanting atmosphere blend into an unforgettable experience. Delight in a delectable lunch and wine tasting experience at a marvellous winery in the heart of Chianti Area. Enjoy Piazza del Campo, renowned for hosting the renowned Palio Horse Race each year. Immerse yourself in the enchanting beauty of San Gimignano, where ancient history blends with the grandeur of medieval towers, offering you an unforgettable journey in Tuscany.

Price: €78

Min age: 0

Rating 4.35 / 5 [705 ratings]

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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: €79

Min age: 0

Rating 4.37 / 5 [3053 ratings]

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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 [13710 ratings]

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Tuscan Cooking Class in Central Siena

Siena

Tuscan Cooking Class in Central Siena
Tuscan Cooking Class. Cooking Class of traditional Tuscan meal from starter to dessert including a fresh home-made pasta at the end of the lesson dinner with all prepared accompanied with Chianti Wine. The maximum number of customers per lesson 15 people. The school has applied all the legal regulations for sanitizing from Coronavirus. The school provides customers with everything necessary established by current safety standards (masks, gels, etc.). Customers actively participate in the preparation of recipes Use of seasonal and local ingredients Vegetarian and gluten-free menus available Customers will learn all the secrets of Italian and Tuscan cuisine and will receive handouts with the prepared recipes Private lessons on request in the morning

Price: €115

Min age: 11

Rating 4.81 / 5 [204 ratings]

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Siena 3h Private Tour

Siena

Siena 3h Private Tour
Discover the treasures of one of the most beautiful cities in the world with a local guide and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. Stroll in the ancient streets and admire the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, Piazza del Campo, Palazzo Pubblico, Palazzo Tolomei, the ancient pilgrims road, the Baptistery and the Cathedral. If you wish you will visit also the inside of the Cathedral, where you will admire the artworks of important Italian artists, such as Michelangelo, Donatello and Bernini. If you are more interested in the Palio tradition, we suggest to visit a Contrada Museum. You will find out why this horse race is so important for the Sienese and admire the prices that they won over the centuries. Customize your tour with your guide!

Price: €130

Min age: 0

Rating 4.74 / 5 [167 ratings]

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena
Enjoy a wine tasting and light lunch in a winery on a full day tour of the Tuscan countryside. Visit San Gimignano a real jewel famous thanks to its stunning towers and discover Orcia Valley with a visit to Montalcino, known all over the world for the production of Brunello di Montalcino.

Price: €140

Min age: 0

Rating 4.60 / 5 [108 ratings]

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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 4.90 / 5 [969 ratings]

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Florence to Tuscany Day Trip with Chianti, Siena & San Gimignano

Florence

Florence to Tuscany Day Trip with Chianti, Siena & San Gimignano
When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and wander the storybook streets of the UNESCO-listed village San Gimignano. Group size is limited to 14 for a more personalized experience.

Price: €176

Min age: 0

Rating 4.71 / 5 [157 ratings]

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Small-Group Chianti Wine-Tasting Trip from Siena

Siena

Small-Group Chianti Wine-Tasting Trip from Siena
Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the region. With your expert guide, visit Castello di Brolio, renowned as the birthplace of Chianti wine. Sample the esteemed Chianti Classico wine, enjoy an authentic Italian lunch at a Tuscan wine estate and tour the cellars to learn about the passion behind this traditional wine directly from the producer. Enjoy some of the region’s best wines directly at the winery. Numbers are limited to eight people on your small-group trip, ensuring you'll receive personalized attention from your guide.

Price: €180

Min age: 0

Rating 4.94 / 5 [55 ratings]

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Hot Air Balloon Flight Over Tuscany from Siena

Siena

Hot Air Balloon Flight Over Tuscany from Siena
Admire the gorgeous landscapes of Tuscany from above on this 1-hour hot air balloon flight from Siena! This thrilling hot air balloon ride takes you up 2,000 feet (609 meters) over the rolling hills, classic Italian villas, imposing castles and sprawling vineyards and olive groves of the Tuscan countryside. Toast to this unforgettable experience with a glass of sparkling wine upon landing. Note: flights are only early in the morning. The exact take -off time will be communicated to you on the basis of the chosen day. He will always be very early in the morning, he will depend on seasonal temperatures.

Price: €310

Min age: 7

Rating 4.68 / 5 [75 ratings]

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Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence

Florence

Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence
Experience a full-day, private tour of the Tuscan gems, Pisa, Siena, and San Gimignano. Let your private driver do all the paperwork and explore Siena, Pisa and San Gimignano at your own pace. With hotel pickup and drop-off from Florence, you will be able to sit back and enjoy the picture postcard Tuscan countryside surrounding you and your travel companions. Make the most out of this private experience with a private and knowledgeable driver at your full disposal. Design with him the itinerary of your dreams!

Price: €474

Min age: 0

Rating 4.81 / 5 [105 ratings]

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Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

Florence

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * With agreements during the reservation we can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lover.

Price: €650

Min age: 0

Rating 4.91 / 5 [231 ratings]

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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.