Recent Searches
Clear
Questions? (888) 651-9785(888) 651-9785

Top Siena Private & Custom Tours

Category
Select Dates
Today
Tomorrow
Filter




Sort: Featured

99 Tours and Activities

Sort by:Featured

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

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.
...  More
  • 4 hours
  • Free Cancellation
From  
US$ 123.51
From  
US$ 123.51
Learn More
  • 4 hours
  • Free Cancellation

Wine Tasting & Winery Tours

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.
...  More
  • 1 to 8 hours
  • Free Cancellation
From  
US$ 202.11
From  
US$ 202.11
Learn More
  • 1 to 8 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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 258.25
From  
US$ 258.25
Learn More
  • 6 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.
...  More
  • 8 hours
From  
US$ 133.61
From  
US$ 133.61
Learn More
  • 8 hours

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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 224.56
From  
US$ 224.56
Learn More
  • 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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 196.49
From  
US$ 196.49
Learn More
  • 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.
...  More
  • 3 hours
  • Free Cancellation
From  
US$ 235.79
From  
US$ 235.79
Learn More
  • 3 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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 145.97
From  
US$ 145.97
Learn More
  • 6 hours
  • Free Cancellation

Vespa, Scooter & Moped Tours

Private VESPA Tour in Tuscany

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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 168.42
From  
US$ 168.42
Learn More
  • 6 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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 291.93
From  
US$ 291.93
Learn More
  • 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.
...  More
  • 3 hours
  • Free Cancellation
From  
US$ 280.70
From  
US$ 280.70
Learn More
  • 3 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.
...  More
  • 2 hours
  • Free Cancellation
From  
US$ 157.19
From  
US$ 157.19
Learn More
  • 2 hours
  • Free Cancellation

Private Sightseeing Tours

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.
...  More
  • Flexible
  • Free Cancellation
From  
US$ 303.16
From  
US$ 303.16
Learn More
  • Flexible
  • Free Cancellation

Historical & Heritage Tours

NEW TO VIATOR

San Galgano and the Tuscan Legend of the Sword in the Rock

A guided tour for all lovers of nature, art and ancient legends!Let yourself be carried away to discover a mystical and unique place in the world, visit the mysterious Abbey of San Galgano and discover the legend of the Templar who, as a sign of renouncing war, cried his sword in the rock.
...  More
  • 2 hours 30 minutes
  • Free Cancellation
From  
US$ 28.07
From  
US$ 28.07
Learn More
  • 2 hours 30 minutes
  • 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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 151.58
From  
US$ 151.58
Learn More
  • 6 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.
...  More
  • 3 hours
  • Free Cancellation
From  
US$ 50.53
From  
US$ 50.53
Learn More
  • 3 hours
  • 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.
...  More
  • 1 to 2 hours
  • Free Cancellation
From  
US$ 11.22
From  
US$ 11.22
Learn More
  • 1 to 2 hours
  • Free Cancellation

Day Trips

NEW TO VIATOR

Vespa tour in Tuscany (Guided)

Follow your vespa mounted professional, experience motorcycle guide, see the countryside, hear the history of the areaWe strongly suggest you should only book this tour if you have some experience of scooter or motorcycle riding. If you do not but have a good aptitude for riding (bikes and road craft) let us know and we should be able to accommodate youThe day's itinerary will be varied according to your needs and desires, we will create a custom route that best meets your wishesPlease specify if you want a scooter for each person or whether you are happy to 'double up'
...  More
  • 6 hours 30 minutes
  • Free Cancellation
From  
US$ 151.58
From  
US$ 151.58
Learn More
  • 6 hours 30 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.
...  More
  • 10 hours
  • Free Cancellation
From  
US$ 213.33
From  
US$ 213.33
Learn More
  • 10 hours
  • Free Cancellation

Private Sightseeing Tours

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

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.
...  More
  • 8 hours
  • Free Cancellation
From  
US$ 247.02
From  
US$ 247.02
Learn More
  • 8 hours
  • Free Cancellation

Half-day Tours

Private Pienza and Montepulciano Half-Day Trip from Siena

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.
...  More
  • 6 hours
  • Free Cancellation
From  
US$ 174.04
From  
US$ 174.04
Learn More
  • 6 hours
  • Free Cancellation

Wine Tasting & Winery Tours

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.
...  More
  • 5 hours
  • Free Cancellation
From  
US$ 134.74
From  
US$ 134.74
Learn More
  • 5 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.
...  More
  • 4 hours
  • Free Cancellation
From  
US$ 73.54
From  
US$ 73.54
Learn More
  • 4 hours
  • Free Cancellation

Historical & Heritage Tours

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. 
...  More
  • 12 hours
  • Free Cancellation
From  
US$ 213.33
From  
US$ 213.33
Learn More
  • 12 hours
  • Free Cancellation


Book online or call
(888) 651-9785
(888) 651-9785