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Top Siena Walking & Biking Tours

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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

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$ 258.27
From  
US$ 258.27
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  • 6 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$ 123.52
From  
US$ 123.52
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  • 4 hours
  • Free Cancellation

City Tours

Best of Siena Guided Walking Tour with Palio Contrada

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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  • 105 to 120 minutes
  • Free Cancellation
From  
US$ 21.34
From  
US$ 21.34
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  • 105 to 120 minutes
  • Free Cancellation

Wine Tasting & Winery Tours

Educational Wine Tour & Tasting in Siena

Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group limited to 12 as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier. Plus, a choice of morning or afternoon departure means you can slot this tour into even the busiest of sightseeing schedules.
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  • 3 hours
  • Free Cancellation
From  
US$ 72.99
From  
US$ 72.99
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  • 3 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$ 224.58
From  
US$ 224.58
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  • 6 hours
  • Free Cancellation

City Tours

Bike tour and wine tasting from Siena

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.
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  • 6 hours
  • Free Cancellation
From  
US$ 145.98
From  
US$ 145.98
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Private Tour: Secret Siena Walking Tour

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
  • Free Cancellation
From  
US$ 235.81
From  
US$ 235.81
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  • 3 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$ 291.96
From  
US$ 291.96
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Private Tour: Siena Walking Tour

Stroll the charming Medieval streets of a Tuscan hill town with this 2-hour private tour of Siena. Learn about Siena's hidden gems from a knowledgeable guide in between visits to its most popular sights.
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  • 2 hours
  • Free Cancellation
From  
US$ 157.21
From  
US$ 157.21
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  • 2 hours
  • Free Cancellation

Day Trips

Bike tour and wine tasting from San Gimignano

Discover the sights and flavors of Tuscany by bike on a private 6-hour tour. Set along gentle roads and trails, the countryside excursion is the perfect way to immerse yourself in the region’s world-famous landscape. Pedal your way to a traditional family farm and wine cellar. There you enjoy a filling meal paired with four different wines. Sample honey and homemade olive oil with bruschettas, cold cuts, and more.
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  • 6 hours
  • Free Cancellation
From  
US$ 151.59
From  
US$ 151.59
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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$ 280.73
From  
US$ 280.73
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  • 3 hours
  • 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$ 50.53
From  
US$ 50.53
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  • 3 hours
  • Free Cancellation

Bike & Mountain Bike Tours

Small Group E-Bike Tour from Siena with Wine Tasting and Lunch

Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena and travel by van into the Chianti hills, where you’ll receive your bike and helmet and will get familiar with the gear. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local winery, where you can enjoy a traditional meal and generous wine tasting.
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  • 8 hours
  • Free Cancellation
From  
US$ 168.44
From  
US$ 168.44
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  • 8 hours
  • 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$ 16.84
From  
US$ 16.84
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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$ 16.84
From  
US$ 16.84
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  • 60 to 90 minutes
  • Free Cancellation

Walking Tours

NEW TO VIATOR

Siena City Game: Family Wars in Medieval Siena

Discover the top attractions & landmarks in Siena in a unique way: by playing a city exploration game on your smartphone. You play a historical role in an ancient political fight. Salimbeni and Tolomei are the two families fighting to gain the power of Siena. But what they don’t know is that another family is out to get them. That family is Terazzini. They choose to stay out of the spotlight and poke the two families to start a war against each other. You are a Terazzini fighting for your family’s cause. Find out secrets about the two families that you can use to harm them. Can you do it?Each riddle you solve will lead you from one place to another, giving you exact directions, so you won’t need a map, a GPS or a guide. When you solve it and guess the answer, the secret story of that place is unlocked.P.S.: After you buy the tour, you will receive an access code that you can to unlock this quest inside the Questo app.
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  • 1 to 2 hours
  • Free Cancellation
From  
US$ 11.22
From  
US$ 11.22
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  • 1 to 2 hours
  • Free Cancellation

Cultural 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
  • Free Cancellation
From  
US$ 202.13
From  
US$ 202.13
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  • 4 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Wine tour with a Sommelier

Take an in-depth tour of the Tuscan wine regions with a certified expert. Your private guide on this journey is a sommelier who is very familiar with the wines and wineries of the area. Spend the day touring two or three wineries, with samplings at each. A delicious Italian lunch at an organic farm is also included. No need to worry about a designated driver, as pickup and drop-off can be included.
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  • 5 hours
  • Free Cancellation
From  
US$ 192.02
From  
US$ 192.02
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  • 5 hours
  • Free Cancellation

Bike & Mountain Bike Tours

Bike tour with wine tasting

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair, includes hotel pickup and drop-off, and finishes with a lunch of Tuscan dishes and wine.
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  • 6 hours
  • Free Cancellation
From  
US$ 145.98
From  
US$ 145.98
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  • 6 hours
  • Free Cancellation

Cultural Tours

A Taste of Rome Private Food Tour: 5 Tastings

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
  • Free Cancellation
From  
US$ 42.67
From  
US$ 42.67
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  • 2 hours
  • Free Cancellation

Street Food Tours

NEW TO VIATOR

Siena Food Tour

After a morning spent exploring the streets of Siena, see to your appetite with a lunchtime Sienese food tour. Enjoy a beautiful antipasto before enjoying a meal in a traditional Tuscan tavern. This culinary tour fits neatly into a long lunch break, making it easy to fit this tour into a full day of sightseeing.
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  • 1 to 2 hours
  • Free Cancellation
From  
US$ 20.21
From  
US$ 20.21
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  • 1 to 2 hours
  • Free Cancellation

Walking Tours

The best of Siena - Private Walking Tour

Enjoy an interesting stroll around the Tuscan jewel of Siena with this 2-hour private walking tour. See the main attractions of the UNESCO-listed city while getting plenty of personal attention from your private guide.
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  • 2 hours
From  
US$ 179.67
From  
US$ 179.67
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  • 2 hours

Private Sightseeing Tours

Expert Led Private Tour of Siena

Nestled in the southern Chianti hills, Siena is, indubitably, one of the most gracious and alluring cities in Italy. The city, best seen from the superior vantage points of the bell tower or the top of the Duomo, is a charming, architecturally harmonized and placid city, filled with glorious Medieval churches, Renaissance palazzos and modern-day preservation efforts. In fact, the entire city center has been put under UNESCO protection, in order to safeguard its unique charm and historic character.During our three hours exploring Siena, we will get a full understanding of the important role Siena has played in many arenas, accompanied by a local expert, who will use her superior insider's viewpoint to foster appreciation for this special corner of the world.From the fan-shaped central piazza, Il Campo, scene of the beloved Palio horse race, to the soaring Duomo, with an elaborate facade by Giovanni Pisano, the walk will pay special attention to Siena's superb artistic heritage.
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  • 3 hours
  • Free Cancellation
From  
US$ 64.00
From  
US$ 64.00
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  • 3 hours
  • Free Cancellation


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(888) 651-9785
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