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Top Siena Private & Custom Tours

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99 Siena Private & Custom Tours

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

Luxury Maremma wine tourWine Tasting & Winery Tours

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$642
From  
US$642
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  • 6 hours
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  • Free Cancellation

Independent Trip to Siena from Florence with Private TransportCultural 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.
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  • 4 hours
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  • Free Cancellation
From  
US$235
From  
US$235
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  • 4 hours
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  • Free Cancellation

Wine tour with a SommelierWine 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
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  • Free Cancellation
From  
US$265
From  
US$265
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  • 5 hours
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  • Free Cancellation

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Private Tour: Siena Walking TourPrivate Sightseeing Tours

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
From  
US$158
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  • 2 hours
  • Free Cancellation

Grape stomping in Tuscan farmhouse from SienaCultural 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$288
From  
US$288
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  • 4 hours
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  • Free Cancellation

Private Excursion to Siena, San Gimignano and Chianti LandscapesPrivate Sightseeing Tours

Private Excursion to Siena, San Gimignano and Chianti Landscapes

star-5
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  
US$469
From  
US$469
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  • 8 hours

Private Walking Tour: Siena and its TreasuresPrivate Sightseeing Tours

Private Walking Tour: Siena and its Treasures

star-5
Siena is one of Tuscany’s most celebrated and in-demand destinations. On this private tour, beat the crowds and enjoy an intimate way of discovering the city. In the company of your guide, you’ll see the shell-shaped Piazza del Campo, admire the distinctive, black-and-white façade of the Duomo, and take in panoramic views from the lofty Facciatone. As you go, learn more about the city’s wealth of history.
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  • 2 hours
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  • Free Cancellation
From  
US$188
From  
US$188
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  • 2 hours
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  • Free Cancellation

Siena City Game: Family Wars in Medieval SienaWalking Tours

Siena City Game: Family Wars in Medieval Siena

Embark on a quest around Siena by solving clues to start a war between the famous Tolomei and Salimbeni families, all with the help of your smartphone. Unlock new stories as you discover on your own the Siena Dome, the historical center, Fonte Gaia, Palazzo Tolomei, and more.+ Discover the second-oldest bank in the world+ Uncover the secrets of the Palazzo Tolomei+ Admire the beautiful fountain at Fonte Gaia+ Take selfies in Piazza del DuomoEach 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. Start and stop whenever you want.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
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  • Free Cancellation
From  
US$12
From  
US$12
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  • 1 to 2 hours
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  • Free Cancellation

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing LunchWine Tasting & Winery Tours

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
From  
US$258
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  • 1 to 8 hours
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  • Free Cancellation

Private Tour: Secret Siena Walking TourPrivate Sightseeing 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$237
From  
US$237
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  • 3 hours
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  • Free Cancellation

Siena Monteriggioni and San Gimignano Fullday from Florence WineTasting IncludedPrivate Sightseeing Tours

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$620
From  
US$620
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  • 10 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouseCultural 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$243
From  
US$243
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  • 4 hours
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  • Free Cancellation

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SienaPrivate Sightseeing Tours

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
From  
US$248
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  • 8 hours
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  • Free Cancellation

Montalcino and Montepulciano Wine Tour from SienaCultural 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
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  • Free Cancellation
From  
US$462
From  
US$462
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  • 6 hours
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  • Free Cancellation

Private Pienza and Montepulciano Half-Day Trip from SienaHalf-day Tours

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
From  
US$271
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  • 6 hours
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  • Free Cancellation

Montalcino and Montepulciano Private TourPrivate Sightseeing Tours

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$428
From  
US$428
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private VESPA Tour in TuscanyVespa, Scooter & Moped Tours

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$338
From  
US$338
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  • 6 hours
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  • Free Cancellation

Siena Monteriggioni and San Gimignano Fullday from Rome WineTasting IncludedHistorical & 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. 
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  • 12 hours
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  • Free Cancellation
From  
US$665
From  
US$665
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  • 12 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENAPrivate Sightseeing Tours

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
From  
US$248
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  • 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Bike tour and wine tasting from SienaCity 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
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  • Free Cancellation
From  
US$237
From  
US$237
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Half-Day Private Chianti Wine Tasting Tour from SienaWine Tasting & Winery Tours

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$136
From  
US$136
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  • 5 hours
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  • Free Cancellation

Private Full-Day Independent Tour to Siena and San Gimignano from FlorenceFull-day Tours

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

star-5
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
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  • Free Cancellation
From  
US$365
From  
US$365
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  • 8 hours
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  • Free Cancellation

Private Tour in Val d'OrciaPrivate 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.
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  • 6 hours
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  • Free Cancellation
From  
US$451
From  
US$451
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Tour: Montalcino Wine Tasting ExperiencePrivate Sightseeing Tours

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
From  
US$282
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  • 8 hours
  • Free Cancellation


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