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55 Siena Cultural Tours

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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Chianti Wine Tasting and San Gimignano Day Trip from SienaDay Trips

Chianti Wine Tasting and San Gimignano Day Trip from Siena

star-4.5
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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  • 5 hours
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  • Free Cancellation
From  
US$47.07 
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US$47.07 
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  • 5 hours
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  • Free Cancellation

Off-Road Tuscan Wine Tour from ChiantiWine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Chianti

Go off-road in a vintage SUV on this Chianti Valley tour from Greve. With a small group of just eight people or fewer, travel through the famous wine-producing region to learn the vintners' secrets. Stop at three cellars for 15 tastings of different varietals as well as local products (olive oil, honey) and a traditional Italian lunch.
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  • 4 hours
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  • Free Cancellation
From  
US$313.81 
Price varies by group size
From  
US$313.81 
Price varies by group size
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  • 4 hours
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  • Free Cancellation

Small Group Tour of SienaCultural Tours

Small Group Tour of Siena

Siena is one of Tuscany’s most picturesque towns, known for its UNESCO-listed center and medieval monuments. This small-group walking tour takes in all the highlights and limited numbers mean extra attention from your guide. Stroll around the grand Piazza del Campo, where the Palio horse race takes place; admire landmarks such as Siena Cathedral; and explore the atmospheric Contrade neighborhood.
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  • 2 hours
  • Free Cancellation
From  
US$72.85 
From  
US$72.85 
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  • 2 hours
  • Free Cancellation

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Grape stomping in Tuscan farmhouseWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse

star-4
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
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  • Free Cancellation
From  
US$240.96 
Price varies by group size
From  
US$240.96 
Price varies by group size
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  • 4 hours
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  • Free Cancellation

Best of Siena Guided Walking Tour Luxury Tours

Best of Siena Guided Walking Tour

star-4.5
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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  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$21.29 
From  
US$21.29 
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  • 1 hour 30 minutes
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  • Free Cancellation

San Gimignano, Chianti, and Montalcino Day Trip from SienaCultural Tours

San Gimignano, Chianti, and Montalcino Day Trip from Siena

star-4.5
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
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  • Free Cancellation
From  
US$112.07 
From  
US$112.07 
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  • 11 hours
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  • Free Cancellation

Siena: City walking tour with Duomo- Skip the lineCultural Tours

Siena: City walking tour with Duomo- Skip the line

star-4.5
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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  • 1 hour 30 minutes to 2 hours
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  • Free Cancellation
From  
US$22.41 
From  
US$22.41 
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  • 1 hour 30 minutes to 2 hours
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  • Free Cancellation

Skip the Line: Siena Duomo and City Walking TourLuxury Tours

Skip the Line: Siena Duomo and City Walking Tour

star-4.5
Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. 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
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  • Free Cancellation
From  
US$33.62 
From  
US$33.62 
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  • 2 hours
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  • Free Cancellation

Off-Road Tuscan Wine Tour from Castellina Dining Experiences

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Off-Road Tuscan Wine Tour from Castellina

star-5
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
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  • Free Cancellation
From  
US$255.53 
US$268.98
US$13.45 savings
Price varies by group size
From  
US$255.53 
US$268.98
US$13.45 savings
Price varies by group size
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  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Tour: Secret Siena Walking TourHalf-day Tours

Private Tour: Secret Siena Walking Tour

star-5
Discover the medieval streets of Siena with a personal guide at your side, and find hidden-away corners far from the tourist crowds. Create a personalized itinerary on this private 3-hour tour, departing from Piazza del Campo in the morning or afternoon. Walk past major monuments as you explore on foot.
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  • 3 hours
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  • Free Cancellation
From  
US$235.36 
per group
From  
US$235.36 
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  • 3 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from FlorenceWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse from Florence

star-5
Get ankle deep in Tuscan tradition on a half-day grape stomping tour from Florence.  Private transportation will take you from your hotel to a winery in the Chianti hills. There, you’ll explore the history and modern practices of winemaking. After tromping on the locally grown grapes, replenish your strength with a homemade lunch and wine tasting, before returning to your accommodation.
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  • 3 hours
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  • Free Cancellation
From  
US$280.19 
Price varies by group size
From  
US$280.19 
Price varies by group size
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  • 3 hours
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  • Free Cancellation

Montalcino and Montepulciano Wine Tour from SienaDay Trips

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
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  • Free Cancellation
From  
US$459.51 
Price varies by group size
From  
US$459.51 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from SienaWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse from Siena

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.
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  • 4 hours
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  • Free Cancellation
From  
US$285.79 
Price varies by group size
From  
US$285.79 
Price varies by group size
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  • 4 hours
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  • Free Cancellation

Montalcino and Montepulciano Private Tour Day Trips

Montalcino and Montepulciano Private Tour

star-5
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
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  • Free Cancellation
From  
US$425.88 
Price varies by group size
From  
US$425.88 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Private Tour in Val d'OrciaDay Trips

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
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  • Free Cancellation
From  
US$448.30 
Price varies by group size
From  
US$448.30 
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  • 6 hours
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  • Free Cancellation

Half-day Private Walking Tour of SienaHalf-day Tours

Half-day Private Walking Tour of Siena

star-5
Siena is one of Tuscany’s most picturesque medieval towns and this private 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
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  • Free Cancellation
From  
US$280.19 
per group
From  
US$280.19 
per group
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  • 3 hours
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  • Free Cancellation

Luxury Montalcino wine tourDay Trips

Luxury Montalcino wine tour

Discover the fine wines of Montalcino, a small town nestled in the hills of Tuscany. After pick-up from the doorstep of your Florence accommodation, your private driver transports you to a vineyard that uses music to age their natural wines. Continue on to Castel Giocondo for a second tasting, followed by a 3-course lunch prepared by Michelin-rated chef Massimo Rossi. Enjoy the meal against a backdrop of the Tuscan countryside.
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  • 6 hours
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  • Free Cancellation
From  
US$616.41 
Price varies by group size
From  
US$616.41 
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  • 6 hours
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  • Free Cancellation

Luxury Maremma wine tourDay Trips

Luxury Maremma wine tour

Get to know the off-the-beaten-path wine region of Maremma, in coastal Tuscany, during this private tour. Round-trip private transportation is convenient and means that you can taste as much wine as you wish. Visit two wineries, both known for their modern architecture, to taste samples and learn about wine production. You'll also enjoy a 3-course lunch and wine pairing.
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  • 6 hours
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  • Free Cancellation
From  
US$638.83 
Price varies by group size
From  
US$638.83 
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  • 6 hours
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  • Free Cancellation

Private Montalcino and Montepulciano Tour from SienaDay Trips

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
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  • Free Cancellation
From  
US$425.88 
Price varies by group size
From  
US$425.88 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Private Siena Traditions TourHalf-day 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
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  • Free Cancellation
From  
US$123.28 
Price varies by group size
From  
US$123.28 
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  • 3 hours
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  • Free Cancellation

A Taste of Rome Private Food Tour: 5 TastingsPrivate Sightseeing Tours

A Taste of Rome Private Food Tour: 5 Tastings

star-5
Discover the flavors of Rome on a 2-hour food tour that highlights the best snacks in the city. Learn about the culinary scene in Rome as your guide takes you to small local eateries for samples of savory and sweet dishes such as pizza, gelato, and cannoli. You’ll also hear live commentary about historical and cultural highlights along the way.
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  • 2 hours
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  • Free Cancellation
From  
US$71.73 
Price varies by group size
From  
US$71.73 
Price varies by group size
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Guided walking tour of Siena Cultural Tours

Guided walking tour of Siena

star-4
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
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  • Free Cancellation
From  
US$16.81 
From  
US$16.81 
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  • 1 hour
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  • Free Cancellation

Kid tour in SienaCultural Tours

Kid tour in Siena

star-4
Explore Siena in a fun and kid-friendly way on this tour created for families with children. As you make your way through the city, your guide will engage young travelers with lively storytelling and riddles to uncover Siena’s secrets. Visitors of all ages will come away with deeper knowledge of local history, art, and traditions. This tour ends with a special surprise gift.
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  • 2 hours
  • Free Cancellation
From  
US$173.72 
per group
From  
US$173.72 
per group
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  • 2 hours
  • Free Cancellation

Siena - Chianti & San Gimignano: Private tour from FlorenceFull-day Tours

Siena - Chianti & San Gimignano: Private tour from Florence

star-5
A day will be dedicated to deepening the roots of traditions, accompanied by an endless enchanted Tuscan scenery, all with a stress-free purpose; private; fully guided tour, a tour to discover many original Italian beauties: history; the art; nature and wine
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  • 8 hours
  • Free Cancellation
From  
US$728.49 
per group
From  
US$728.49 
per group
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  • 8 hours
  • Free Cancellation


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