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Top Siena Private Sightseeing Tours

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96 Tours and Activities

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

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  
$293.55
From  
$293.55
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  • 6 hours
  • Free Cancellation

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  
$259.68
From  
$259.68
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  • 6 hours
  • Free Cancellation

Pisa and Lucca PRIVATE TOUR from Siena

Go beyond Siena to discover Pisa and Lucca with your own private guide, and build a customized itinerary around the sights you want to see most. After leaving your hotel or the port, you’ll travel north into Tuscany to check out the landmarks and history of Pisa’s Piazza dei Miracoli. See the Leaning Tower of Pisa and more, then continue to the Etruscan city of Lucca to learn the history behind its beguiling city walls.
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  • Flexible
  • Free Cancellation
From  
$304.84
From  
$304.84
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  • Flexible
  • Free Cancellation

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  
$152.42
From  
$152.42
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  • 6 hours
  • Free Cancellation

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  
$134.35
From  
$134.35
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  • 8 hours

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.
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  • 1 to 8 hours
  • Free Cancellation
From  
$203.22
From  
$203.22
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  • 1 to 8 hours
  • Free Cancellation

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  
$158.06
From  
$158.06
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  • 2 hours
  • Free Cancellation

Pienza Val d'Orcia Montalcino Brunello Wine and Pecorino Cheese PRIVATE TOUR from Siena

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury Mercedes vehicle with a private guide who shares the best of the region.
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  • 8 hours
  • Free Cancellation
From  
$248.39
From  
$248.39
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  • 8 hours
  • Free Cancellation

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  
$282.26
From  
$282.26
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  • 3 hours
  • Free Cancellation

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  
$124.19
From  
$124.19
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  • 4 hours
  • Free Cancellation

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  
$193.06
From  
$193.06
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  • 5 hours
  • Free Cancellation

Private Full-Day Independent Tour to Siena and San Gimignano from Florence

Siena and San Gimignano are two of Tuscany’s most picturesque medieval towns, but visiting on a group tour often means limited time for sightseeing. This private full-day tour from Florence offers plenty of time to explore the UNESCO-listed towns independently, with private transport and an itinerary tailored to your preferences.
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  • 8 hours
  • Free Cancellation
From  
$108.39
From  
$108.39
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  • 8 hours
  • Free Cancellation

NEW TO VIATOR

Siena - Chianti & San Gimignano: Private tour from Florence

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  
$733.87
From  
$733.87
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  • 8 hours
  • Free Cancellation

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  
$237.10
From  
$237.10
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  • 3 hours
  • Free Cancellation

Private Tour: Guided Hike in Tuscany with Transport from Siena

Drench yourself in the fabled Tuscan countryside with this private, day-long hiking tour from Siena. Meet your expert guide in Siena and then drive in a comfortable minivan to the trail where you’ll perambulate through verdant vineyards, rustic villages, and over the classic rolling hills of Tuscany. Stop halfway along the hike to indulge in a classic lunch of Tuscan treats and then travel via minivan to the town of San Gimignano, known as the ‘medieval Manhattan’ for its many gothic towers that form a medieval skyline in the 21st century. 
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  • 7 hours
  • Free Cancellation
From  
$117.42
From  
$117.42
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  • 7 hours
  • Free Cancellation

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  
$146.77
From  
$146.77
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  • 6 hours
  • Free Cancellation

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  
$73.95
From  
$73.95
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  • 4 hours
  • Free Cancellation

Half-Day Private Chianti Wine Tasting Tour from Siena

The Chianti wine region is renowned for producing some of the finest Tuscan wines and this private half-day tasting tour from Siena is the ideal introduction. Explore the historic villages of Radda and Vertine, enjoy wine tasting at a local wine estate, and learn more about Tuscany’s winemaking history from your expert guide.
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  • 5 hours
  • Free Cancellation
From  
$135.48
From  
$135.48
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  • 5 hours
  • Free Cancellation

Private Van: Chianti Wine experience day trip from Siena

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent wines.  • Visit small villages such as Greve, Castellina and Radda in Chianti and ancient castles, hidden among green hills and surrounded by vineyards and olive groves. • This tour is a perfect combination of culinary delights, arts and culture. This private tour can be customized from locations you visit to the starting time of the tour.
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  • 8 hours
  • Free Cancellation
From  
$525.00
From  
$525.00
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  • 8 hours
  • Free Cancellation

NEW TO VIATOR

Vespa tour in Tuscany (Guided)

Follow your vespa mounted professional, experience motorcycle guide, see the countryside, hear the history
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  • 6 hours 30 minutes
  • Free Cancellation
From  
$152.42
From  
$152.42
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  • 6 hours 30 minutes
  • Free Cancellation

Truffle Hunting with Wine Tasting in Tuscan farmhouse

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.
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  • 4 hours
  • Free Cancellation
From  
$135.48
From  
$135.48
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  • 4 hours
  • Free Cancellation

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  
$22.58
From  
$22.58
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  • 2 hours
  • Free Cancellation

SPECIAL OFFER

Siena Mobile Exploration Game: Battle for Duomo

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  
$5.63
$11.28
$5.65 savings
From  
$5.63
$11.28
$5.65 savings
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  • 1 to 2 hours
  • Free Cancellation

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  
$214.51
From  
$214.51
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  • 10 hours
  • Free Cancellation


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(888) 651-9785
(888) 651-9785