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Top Siena Cultural & Theme Tours

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Day Trips

Chianti Wine Tasting and San Gimignano Day Trip from Siena

Soak up the local vino and small-town charm of San Gimignano with 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, where you’ll enjoy an intimate winery tour. Sip and swirl Chianti blends with an inside look at the wine-making process. Your trip will conclude back in Siena.
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  • 5 hours
  • Free Cancellation
From  
US$ 47.17
From  
US$ 47.17
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  • 5 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Chianti and Castle Tour from Siena

Take the stress out of planning a day in Tuscany with this 5-hour 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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  • 5 hours
  • Free Cancellation
From  
US$ 67.39
From  
US$ 67.39
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  • 5 hours
  • Free Cancellation

Walking Tours

Skip the Line: Siena Duomo and City Walking Tour

Indulge in one of Italy's most beautiful cities. This 2-hour sightseeing tour, led by an expert guide, gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket. 
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  • 2 hours
  • Free Cancellation
From  
US$ 33.69
From  
US$ 33.69
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  • 2 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Castellina

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at three wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop. The tour starts and ends in the village of Castellina in Chianti.
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  • 4 hours
  • Free Cancellation
From  
US$ 179.70
From  
US$ 179.70
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  • 4 hours
  • Free Cancellation

Day Trips

San Gimignano, Chianti, and Montalcino Day Trip from Siena

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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  • 11 hours
  • Free Cancellation
From  
US$ 112.31
From  
US$ 112.31
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  • 11 hours
  • Free Cancellation

Cultural Tours

Montalcino and Montepulciano Wine Tour from Siena

Explore the Val d'Orcia Region of Tuscany on a private, full-day tour. Stop in Montepulciano to soak up the history of the medieval town and visit a winery where you taste the region’s wines. Sit down for a traditional Tuscan lunch before continuing on to Pienza, a fifteenth-century village filled with antique shops and known to be the birthplace of Pecorino cheese. Finally stop in Montalcino and tastethe sought after Brunello di Montalcino wines while you admire the vineyards and olive groves.
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  • 6 hours
  • Free Cancellation
From  
US$ 258.32
From  
US$ 258.32
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  • 6 hours
  • Free Cancellation

Day Trips

Small-Group San Gimignano and Volterra Day Trip from Siena

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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  • 8 hours
  • Free Cancellation
From  
US$ 157.24
From  
US$ 157.24
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  • 8 hours
  • Free Cancellation

Cultural Tours

Grape stomping in Tuscan farmhouse

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills.  Explore a local vinyard with your private guide and discover the wine making process. In addition to living out your Italian dreams of crushing grapes with your bare feet, you’ll also enjoy a wine tasting, along with a homemade lunch.
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  • 4 hours
  • Free Cancellation
From  
US$ 123.54
From  
US$ 123.54
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  • 4 hours
  • Free Cancellation

Private Sightseeing Tours

Private Excursion to Siena, San Gimignano and Chianti Landscapes

Explore the Chianti countryside on this full-day private tour of Siena and San Gimignano. Departing from Florence, head first to Siena for a walking tour of the city’s medieval streets. Admire the palaces and Piazza del Campo, followed by time to explore independently. Then travel via the fortified village of Monteriggioni to the town of San Gimignano and discover the medieval architecture and art on your own. Afterward, reunite with your private driver to travel back to Florence.
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  • 8 hours
From  
US$ 133.65
From  
US$ 133.65
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  • 8 hours

Historical & Heritage Tours

Siena Vespa Tour Including Lunch at a Chianti Winery

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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  • 8 hours
  • Free Cancellation
From  
US$ 112.31
From  
US$ 112.31
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  • 8 hours
  • Free Cancellation

Cultural Tours

Private Montalcino and Montepulciano Tour from Siena

Travelling in Val d'Orcia is an unforgettable experience. Your eyes become dazzled by the beauty of the colours of this land, unsurprisingly a UNESCO World Heritage Site. This tour has been created for you to discover the most painted corner of Tuscany, made of enchanted landscapes, tree-lined avenues. Sunrises and sunsets of extraordinary, unique colours in the world are one great addition when wandering the road from Montepulciano to Montalcino through Pienza, considered one of the most amazing routes of Italy.
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  • 6 hours
  • Free Cancellation
From  
US$ 224.62
From  
US$ 224.62
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Private Tour in Val d'Orcia

Discover the natural beauty of Italy's Val d'Orcia on this private tour that introduces you to the postcard-perfect scenery of rolling hills and vineyards. You'll visit the towns of Montepulciano, Pienza, and Montalcino; tour a winery; and enjoy included wine tastings and a Tuscan lunch for a well-rounded experience in this UNESCO World Heritage–listed valley.
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  • 6 hours
  • Free Cancellation
From  
US$ 196.55
From  
US$ 196.55
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  • 6 hours
  • Free Cancellation

Day Trips

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

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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  • 8 hours
  • Free Cancellation
From  
US$ 95.47
From  
US$ 95.47
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  • 8 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Half-Day Brunello di Montalcino Wine Tour from Siena

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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  • 5 hours
  • Free Cancellation
From  
US$ 67.39
From  
US$ 67.39
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  • 5 hours
  • Free Cancellation

Private Sightseeing Tours

Montalcino and Montepulciano Private Tour

Explore the beautiful Val d’Orcia just outside of Florence on this private full-day tour. Drive through the rolling countryside to visit the picturesque towns of Montepulciano, Pienza, and Montalcino. Sample wines from local vineyards and sit down to a delicious lunch made with fresh ingredients from the region. Discover the Tuscany that appears in movies and on postcards during this tour and admire the beautiful landscapes.
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  • 6 hours
  • Free Cancellation
From  
US$ 292.01
From  
US$ 292.01
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Half-day Private Walking Tour of Siena

Siena is one of Tuscany’s most picturesque medieval towns and this private 3-hour walking tour is ideal for first-time visitors or those short on time. Take in the highlights of the UNESCO-listed center, stroll around lively Piazza Del Campo, and admire landmarks such as San Domenico basilica, Palazzo Tolomei, and Cathedral of Siena.
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  • 3 hours
  • Free Cancellation
From  
US$ 280.78
From  
US$ 280.78
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  • 3 hours
  • Free Cancellation

Cultural Tours

Siena Walking Tour

The UNESCO–listed city of Siena ranks among Italy’s must-see destinations, with medieval history, beautiful architecture, and colorful culture. On this walking tour, choose from a range of start times and take in top city attractions including the Piazza del Campo and Chigi Palace. Enjoy a concise introduction to the best of Siena, and navigate easily as your guide brings the city’s history to life. Upgrade your tour to include a visit to Siena Cathedral—the city’s top attraction.
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  • 60 to 90 minutes
  • Free Cancellation
From  
US$ 16.85
From  
US$ 16.85
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  • 60 to 90 minutes
  • Free Cancellation

Cultural Tours

Private Siena Traditions Tour

Delve into Siena’s wealth of history—and learn all about the storied Palio horse race, which takes place in the city twice a year—on this private walking tour. Meet your guide in the morning at your local accommodation or in the city center, and explore Siena’s UNESCO-listed sights. See the Piazza del Campo, where the race is held, and visit one of the 17 contrade (districts) that compete. As you go, your guide will share stories and lore about this centuries-old event.
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  • 3 hours
  • Free Cancellation
From  
US$ 50.54
From  
US$ 50.54
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  • 3 hours
  • Free Cancellation

Cultural Tours

Discover the life of Saint Catherine of Siena

Learn about Saint Catherine of Siena, the patron Saint of Italy and Europe, on a 2-hour tour of her hometown. Visit landmarks such as the birthplace of Saint Catherine in Siena, and sacred sites related to her life. Your guide shows you where she worked, studied, and was buried, and shares commentary about her importance.
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  • 75 to 135 minutes
  • Free Cancellation
From  
US$ 13.48
From  
US$ 13.48
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  • 75 to 135 minutes
  • Free Cancellation

Cultural Tours

NEW TO VIATOR

Guided walking tour of Siena

iena 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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  • 1 hour
  • Free Cancellation
From  
US$ 16.85
From  
US$ 16.85
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  • 1 hour
  • Free Cancellation

Literary, Art & Music Tours

NEW TO VIATOR

Tour guiado de Siena en español

Un agradable paseo de una hora para introducirte en la historia y en las bellezas artísticas de la ciudad, así como en las anécdotas y personajes que han contribuido a hacer de Siena una de las ciudades más célebres de Italia. El tour incluye la posibilidad de terminar con la visita a la Catedral (la entrada no está incluída en el precio).
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  • 60 to 90 minutes
  • Free Cancellation
From  
US$ 16.85
From  
US$ 16.85
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  • 60 to 90 minutes
  • Free Cancellation

Private Sightseeing Tours

Siena Monteriggioni and San Gimignano Fullday from Florence WineTasting Included

Take a delightful detour from Florence to explore other gems of Tuscany on this private, full-day tour. Marvel at the Leaning Tower of Pisa and other architectural highlights of Piazza dei Miracoli, and wander through the cobblestone streets and squares of medieval San Gimignano and Siena, both honored as UNESCO World Heritage sites. Travel through the scenic countryside in a private minivan, and enjoy the flexibility of a fully customizable tour.
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  • 10 hours
  • Free Cancellation
From  
US$ 213.39
From  
US$ 213.39
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  • 10 hours
  • Free Cancellation

Historical & Heritage Tours

Enogastronomic Tour from Siena: Montalcino, Pienza and Montepulciano

Taste your way through Tuscany with this 9-hour 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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  • 9 hours
  • Free Cancellation
From  
US$ 61.77
From  
US$ 61.77
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  • 9 hours
  • Free Cancellation

Cultural Tours

Independent Trip to Siena from Florence with Private Transport

Cast your sightseeing net wider than Florence to experience another Tuscan gem  — Siena — as you wish. This independent 4-hour round-trip whisks you by private vehicle to the UNESCO-listed town, leaving you to stroll and sightsee independently. Explore the medieval lanes, see sights such as Siena Cathedral and Tower of Mangia, shop for souvenirs, and enjoy the Piazza del Campo, home to Siena’s Il Palio horse races. Central Florence hotel pickup and drop-off included.
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  • 4 hours
  • Free Cancellation
From  
US$ 73.56
From  
US$ 73.56
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  • 4 hours
  • Free Cancellation


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