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Top Siena Private Sightseeing Tours

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101 Siena Private Sightseeing Tours

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

Brunello di Montalcino wine experience with a sommelier from Siena

Brunello di Montalcino wine experience with a sommelier from Siena

star-5
One of the best wine region of the world with a local driving-guide and wine connoisseur, born and raise in the area.Private tour in two boutique wineries , driving through the most scenic road of Val d'Orcia with chance to stop for the best Tuscan countryside pictures.
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  • 5 to 6 hours
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  • Free Cancellation
From  
US$169.64 
From  
US$169.64 
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  • 5 to 6 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse

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$243.15 
From  
US$243.15 
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  • 4 hours
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  • Free Cancellation

Montalcino and Montepulciano Wine Tour from Siena

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$463.69 
From  
US$463.69 
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  • 6 hours
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  • Free Cancellation

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Private Tour: Siena Walking Tour

Private Tour: Siena Walking Tour

star-5
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$158.33 
From  
US$158.33 
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  • 2 hours
  • Free Cancellation

Wine tour with a Sommelier

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
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  • Free Cancellation
From  
US$265.77 
From  
US$265.77 
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  • 5 hours
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  • Free Cancellation

Half-Day Private Chianti Wine Tasting Tour from Siena

Half-Day Private Chianti Wine Tasting Tour from Siena

star-4.5
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
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  • Free Cancellation
From  
US$135.71 
From  
US$135.71 
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  • 5 hours
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  • Free Cancellation

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

star-5
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
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  • Free Cancellation
From  
US$258.99 
From  
US$258.99 
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  • 1 to 8 hours
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  • Free Cancellation

Private Tour: Secret Siena Walking Tour

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$237.50 
From  
US$237.50 
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  • 3 hours
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  • Free Cancellation

Siena Monteriggioni and San Gimignano Fullday from Florence WineTasting Included

Siena Monteriggioni and San Gimignano Fullday from Florence WineTasting Included

star-5
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
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  • Free Cancellation
From  
US$622.02 
From  
US$622.02 
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  • 10 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from Florence

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$282.74 
From  
US$282.74 
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  • 3 hours
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  • Free Cancellation

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Siena

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Siena

star-5
Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury Mercedes vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.
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  • 8 hours
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  • Free Cancellation
From  
US$248.81 
From  
US$248.81 
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  • 8 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from Siena

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$288.39 
From  
US$288.39 
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  • 4 hours
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  • Free Cancellation

Private Pienza and Montepulciano Half-Day Trip from Siena

Private Pienza and Montepulciano Half-Day Trip from Siena

star-5
Discover the beauty of the Tuscan Val d'Orcia region on a day trip to Pienza and Montepulciano with your own private driver. After leaving Siena, you'll travel through the village of Buonconvento and then into the idyll of gentle hills and stone hamlets that typify the Tuscan landscape. Spend time in Pienza, exploring its artisan shops and trying its famous pecorino cheese, then continue to medieval Montepulciano for a winery visit and tasting.
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  • 6 hours
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  • Free Cancellation
From  
US$271.43 
From  
US$271.43 
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  • 6 hours
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  • Free Cancellation

Montalcino and Montepulciano Private Tour

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$429.76 
From  
US$429.76 
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  • 6 hours
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  • Free Cancellation

Tuscany Tour in English from Florence

Tuscany Tour in English from Florence

star-5
Experience Tuscany during this full-day, private, guided tour that includes lunch and a wine tasting (select option at booking). Visit this storied region with up to eight people and enjoy free time to explore four separate stops including Pisa and Monteriggioni. Wander in Tuscan villages, explore history, see medieval architecture and share your photos using the vehicle’s free, onboard WiFi.
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  • 10 to 11 hours
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  • Free Cancellation
From  
US$995.23 
From  
US$995.23 
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  • 10 to 11 hours
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  • Free Cancellation

Private VESPA Tour in Tuscany

Private VESPA Tour in Tuscany

star-5
Experience the Tuscan countryside from a perspective rare to visitors on a private Vespa tour with round–trip transport from your Siena hotel. In addition to navigating for you, your guide ensures the best views and stops for photo opportunities along the way. The day includes a Tuscan–style lunch and complimentary wine tasting with vineyard views.
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  • 6 hours
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  • Free Cancellation
From  
US$339.28 
From  
US$339.28 
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  • 6 hours
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  • Free Cancellation

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

star-5
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
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  • Free Cancellation
From  
US$248.81 
From  
US$248.81 
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  • 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Bike tour and wine tasting from Siena

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
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  • Free Cancellation
From  
US$237.50 
From  
US$237.50 
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  • 6 hours
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  • Free Cancellation

Siena Monteriggioni and San Gimignano Fullday from Rome WineTasting Included

Siena Monteriggioni and San Gimignano Fullday from Rome WineTasting Included

Explore the picturesque towns of Pisa and San Gimignano on this all-day tour from Rome. After a convenient hotel pickup, travel by private minivan with an informative English-speaking driver to the Tuscan countryside. Customize your own itinerary to include sites like the city’s iconic leaning tower, Piazza dei Miracoli, and the walled medieval hill town of San Gimignano. Then, enjoy a wine tasting included in the tour price. 
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  • 12 hours
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  • Free Cancellation
From  
US$667.26 
From  
US$667.26 
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  • 12 hours
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  • Free Cancellation

Private Tour in Val d'Orcia

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$452.38 
From  
US$452.38 
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  • 6 hours
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  • Free Cancellation

Truffle Hunting Private Experience in Siena

Truffle Hunting Private Experience in Siena

star-5
Discover the art of truffle hunting firsthand on a private 2-hour tour in the morning or evening. Benefit from the expertise of your local guide and his dogs as you learn about the secrets of finding truffles, training the dogs, and culinary uses for the celebrated mushrooms. Finish the tour by tasting truffle products in central Sienna, or opt to stay for a meal (own expense) that features the fresh truffles.
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  • 2 hours
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  • Free Cancellation
From  
US$124.40 
From  
US$124.40 
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  • 2 hours
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  • Free Cancellation

Private Tour: Montalcino Wine Tasting Experience

Private Tour: Montalcino Wine Tasting Experience

star-5
Sip some of Italy's best vino with a private full-day wine tour in Montalcino from Cortona. Visit two wineries to taste the famous Brunello wines produced in this part of Tuscany. Learn what makes Brunello so special from sommeliers and wine experts. Sample a selection of Tuscan meats and cheeses with the wine. Have lunch in a winery and visit either Montalcino or the Sant'Antimo Abbey before the end of the tour.
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  • 8 hours
  • Free Cancellation
From  
US$282.74 
From  
US$282.74 
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  • 8 hours
  • Free Cancellation

Half-day Private Walking Tour of Siena

Half-day Private Walking Tour of Siena

star-5
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
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  • Free Cancellation
From  
US$282.74 
From  
US$282.74 
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  • 3 hours
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  • Free Cancellation

Bike tour with wine tasting

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
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  • Free Cancellation
From  
US$226.19 
From  
US$226.19 
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  • 6 hours
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  • Free Cancellation


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