Top Siena Historical Tours
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74 results | All Siena Tours
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Siena Vespa Tour Including Lunch at a Chianti Winery
52
See the hills of Tuscany in true Italian style with this action-packed day trip on a Vespa scooter from Siena. Set off on your scooter through the Tuscan countryside, your guide leading the way, as you and other scooter-riding participants make your way to a Chianti winery for lunch. Tour the vineyards and cellars, sample some wine and indulge in an antipasto lunch before heading back to Siena.
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From
$156.97
From
$156.97

Chianti Wine Tasting and San Gimignano Day Trip from Siena
203
Soak up the local vino and small-town charm of San Gimignano on this wine tasting trip from Siena. Explore San Gimignano first at your leisure, spotting landmarks such as the Collegiata and Pizza del Duomo while strolling the medieval streets. Afterward, travel deeper into the Tuscan hills, and enjoy an intimate winery tour. Sip and swirl Chianti blends with an inside look at the winemaking process.
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From
$51.11
From
$51.11
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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Small-Group Montepulciano and Pienza Day Trip from Siena
78
Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.
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From
$170.36
From
$170.36
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Chianti and Castle Tour from Siena
43
Take the stress out of planning a day in Tuscany on this half-day small-group tour of the Chianti wine region from Siena, including transport. Enjoy an air-conditioned ride over to two popular wineries to taste wines and oils locals love. Plus spend some free time in Monteriggioni, and catch a glimpse of the town’s well-known medieval castle.
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From
$85.18
From
$85.18
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Small-Group San Gimignano and Volterra Day Trip from Siena
48
Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide.
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From
$170.36
From
$170.36
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Siena Top 10 Pula Tour
16
Our Polaguides will allow you to discover the most hidden places, but no less fascinating than Siena and instant photography will allow you to appreciate the beauty 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 personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.
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From
$42.52
per group
From
$42.52
per group

San Gimignano, Chianti, and Montalcino Day Trip from Siena
30
Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.
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From
$121.69
From
$121.69
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
22
See Tuscany in classic Italian style by exploring the rustic region via a vintage Fiat 500, the classic, beloved and diminutive Italian automobile. Get picked up at your hotel in Siena and then ride to the stunning hilltop town of Monteriggioni, cruising through the rolling hills of Chianti along the way. Stop at a local vineyard and sample some delicious Italian wines with a hearty lunch of local fare. Follow the guide in a caravan. The number of participants on this small-group tour is limited to just ten, so you’re sure to get plenty of personalized attention from the guide.
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From
$182.53
From
$182.53
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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From Siena: Pienza and Montepulciano Wine Tour
34
Taste your way through Tuscany with this full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano and Montalcino.
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From
$66.93
From
$66.93
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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Small-Group Chianti and San Gimignano Sunset Trip from Siena
23
Sip world-class wine and watch the sunset on this day trip to Chianti and San Gimignano from Siena. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills. Group size is reserved for eight people to keep the experience as intimate as possible.
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From
$182.53
From
$182.53
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Half-Day Brunello di Montalcino Wine Tour from Siena
13
Spend an afternoon in the wine town of Montalcino, tasting the prestigious Brunello di Montalcino and learning about wine production. This tour from Siena that tasting of local wine paired with salami and cured meat. Admire views of the Tuscan countryside from the pretty hill town and discover the region’s generations-old winemaking traditions.
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From
$85.18
From
$85.18
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Best of Siena Guided Walking Tour
15
Maximize time in Siena with a guided walking tour through the medieval city streets. See local landmarks including Piazza del Campo and the Siena Cathedral while hearing stories about the city’s history and architecture from a local guide. Explore a local district, called a Contrada, and learn about Siena’s famous Palio horse races.
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From
$23.12
From
$23.12
Face masks required for travelers in public areas
Face masks required for guides in public areas
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Siena Historic City Walking Tour with Cathedral Option
41
Discover the treasures of one of the most beautiful cities in the world with a monolingual local guide and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. With a small group you will explore the best that Siena has to offer. Your guide will accompany you along the ancient streets of Siena through the most beautiful sites such as: Piazza del Campo, Palazzo Pubblico, Palazzo Tolomei, Palazzo Salimbeni, the ancient via Banchi di Sopra, the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, the Baptistery and the Cathedral. You will visit also the inside of the Cathedral (ticket not included), if you choose the Cathedral option, where you will admire the works of art of important Italian artists, such as Michelangelo, Donatello and Bernini.
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From
$24.34
From
$24.34
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
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Guided walking tour of Siena
13
Siena is a treasure trove of historical, artistic, religious and cultural riches all to be discovered.
The best way to do it is on foot, admiring the changes to the town over the centuries and enjoying the spectacular scenery and curious particulars. With an authorized guide you will be able to appreciate the major tourist attractions like Piazza del Campo, the true heart of the town, the Palazzo Comunale (Town Hall), the Cathedral and the majestic Basilica of San Domenico. There will also be no lack of references to the great noble families, such as the Piccolomini, Tolomei and Salimbeni, and their palazzos, to the great tradition of the Siena Palio, but also to the stories of pilgrimage and saintliness that distinguish the town. The walk continues with a visit to the Cathedral that preserves the treasures of artists like Nicola Pisano, Duccio di Buoninsegna, Donatello and Gianlorenzo Bernini, besides its marvelous marble floor, which is a unique example in the history of art.
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From
$24.34
From
$24.34
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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E-Bike Tour in Val d'Orcia
9
Pedal through rolling hills and medieval villages in the scenic Val d’Orcia on an e-bike tour that includes lunch and an on-farm cheese tasting. With a guide to select the safest and most scenic bike routes through the UNESCO-listed agricultural region, you can focus on the experience. Provided e-bikes mean this tour can be as challenging—or as relaxed—as you want.
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From
$267.71
Price varies by group size
From
$267.71
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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PolaTour The 17 Fountains of the Contradas of Siena
6
Our Polaguides will allow you to discover the most hidden places, but no less fascinating than Siena and its districts and instant photography will allow you to appreciate the beauties of each district 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 personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.
…More
From
$40.01
per group
From
$40.01
per group

CSTRents - Siena Segway PT Authorized Tour
2
Mix medieval times with the 21st century on this small-group or private 3-hour tour of Siena via Segway. Gliding around town on two wheels, follow your guide while learning about the history of the town and each place you visit. See this Tuscan town’s main attractions from a Segway, including Piazza del Campo, Piazza del Duomo and Basilica of San Domenico. Get a killer view from the imposing Fortezza Medicea. Opt to take the tour in the morning, afternoon or in the evening to better suit your time in Siena. The number of participants on this small-group tour is limited to just eight, so you’re sure to get plenty of personalized attention from the guide.
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From
$181.29
Price varies by group size
From
$181.29
Price varies by group size
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Gear/equipment sanitized between use
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Siena: Guided tour of Siena INCLUDED Duomo
3
Wonderful Tour of Classic Siena every Saturday and Sunday guaranteed departure at 11.00 am from Piazza Duomo.
Expert local guide will introduce you, in an interesting and pleasant way, to the history of Siena, the Duomo, Piazza del Campo and other monuments of the city. We will talk about the Palio, the districts and visit the lesser known and most peaceful corners of the city. Duomo skip the line included
adult rate 25.00 euros per person
children between 6 and 12 years 10.00 euro per person
children under 6 years free
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From
$30.42
From
$30.42
Face masks required for travelers in public areas
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Private Tour of Siena Cathedral
1
Opt for a personalized experience of Siena’s top attraction on a private tour of Siena Cathedral (Il Duomo). With just your private guide and party, you’ll discover easy-to-miss details in the cathedral’s interior and benefit from commentary integral to understanding the statues of Michelangelo and the art inside the Chapel of St. John the Baptist. Plus, booking in advance means you’ll save hours of waiting in line with a skip-the-line admission ticket.
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From
$182.53
per group
From
$182.53
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
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Private Tour - San Galgano Abbey the Tuscan Legend of the Sword in the Rock
2
A guided tour for all lovers of nature, art and ancient legends!
Let yourself be carried away to discover a mystical and unique place in the world, visit the mysterious Abbey of San Galgano and discover the legend of the Templar who, as a sign of renouncing war, cried his sword in the rock.
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From
$106.09
From
$106.09
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
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Siena 2-hour private tour with an expert guide
1
Benefit from the personalized attention of your private guide on this 2-hour walking tour of Siena. Hear about the history and culture of this city, which is listed as a UNESCO World Heritage Site. You’ll take in landmarks such as the Siena Cathedral, Piazza del Campo, and more as you stroll around the picturesque streets at a pace that is suitable for most people.
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From
$121.69
Price varies by group size
From
$121.69
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More

PolaTour Palio of Siena
Our Polaguides will allow you to discover the most hidden places, but no less fascinating and important for Siena and the Palio, besides instant photography will allow you to appreciate the beauty 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 personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.
…More
From
$40.01
per group
From
$40.01
per group

Siena Running Tour
Siena Running Tour is a new way of visiting the city by exploiting the potential of running and combining fitness and culture. Visitors will have the opportunity to cover a geographical space wider than what you can usually see with a classic visit on foot and enjoy unaspected views. The starting point is the Fortezza Medicea, a traditional Sienese fitness place, from which your guide will give you a wide introduction to the history of the city, taking advantage of the spectacular view of the Cathedral, of the Torre del Mangia, of the ancient hospital of Santa Maria della Scala, in short, of the most important monuments of Siena, as well as, of course, of the fortress itself. Then we will proceed towards the city center, the Market square, ending the tour in Piazza Salimbeni, historical site of the Monte dei Paschi di Siena bank.
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From
$200.04
per group
From
$200.04
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Siena photo tour
Siena photo tour is a new way of seeing Siena through the eyes of a local who will guide you through the city showing you its hidden treasures, panoramas, medieval towers, churches and palaces, alleys that otherwise alone you would never find and green valleys within the city walls. During the explanations you will have all the time you need to take pictures and ask the guide every question and curiosity that passes through your mind. At the end of the tour your eyes will be full of unforgettable images of Siena!
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From
$175.03
per group
From
$175.03
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
- Siena Cathedral Museum (Museo dell’Opera Metropolitana)
- National Art Gallery of Siena (Pinacoteca Nazionale Siena)
- Mangia Tower (Torre del Mangia)
- Siena Historic Center (Siena Centro Storico)
- Baptistery of San Giovanni (Battistero di San Giovanni)
- Santa Maria della Scala
- Fonte Gaia (Gaia Fountain)
- Piccolomini Library (Libreria Piccolomini)
- Montalcino Fortress (Fortezza di Montalcino)
- Palio of Siena (Palio di Siena)
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- Things to do in Chianti
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