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Top Siena Luxury & Special Occasions

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65 Siena Luxury & Special Occasions

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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

Montepulciano Wine Tour ( 3 wineries and lunch )Wine Tasting & Winery Tours

Montepulciano Wine Tour ( 3 wineries and lunch )

star-4.5
Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.
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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

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

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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

Skip the Line: Siena Duomo and City Walking TourWalking Tours

Skip the Line: Siena Duomo and City Walking Tour

star-4.5
Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. 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
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  • Free Cancellation
From  
US$34
From  
US$34
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  • 2 hours
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  • 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

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

Off-Road Tuscan Wine Tour from CastellinaWine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Castellina

star-5
Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at three wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop. The tour starts and ends in the village of Castellina in Chianti.
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  • 4 hours
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  • Free Cancellation
From  
US$271
From  
US$271
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  • 4 hours
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  • Free Cancellation

Best of Siena Guided Walking TourCultural Tours

Best of Siena Guided Walking Tour

star-4.5
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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  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$22
From  
US$22
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  • 1 hour 30 minutes
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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

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

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
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  • 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

Heart of Chianti Classico - 3 Wineries and Lunch - Chianti Wine TourWine Tasting & Winery Tours

Heart of Chianti Classico - 3 Wineries and Lunch - Chianti Wine Tour

star-4
Discover the heart of the Chianti region—Chianti Classico—on this day tour from Siena or Florence. Traveling by Mercedes minivan limited to eight people, you'll get to know one of Italy's most famous wine regions as you visit three wineries, partake in tastings of more than 15 wines, and fill up on an included lunch.
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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

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
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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

Half-day Private Walking Tour of SienaPrivate Sightseeing Tours

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
From  
US$282
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  • 3 hours
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  • Free Cancellation

Bike tour with wine tastingBike & 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
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  • Free Cancellation
From  
US$226
From  
US$226
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  • 6 hours
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  • Free Cancellation

Luxury Montalcino wine tourWine Tasting & Winery Tours

Luxury Montalcino wine tour

Discover the fine wines of Montalcino, a small town nestled in the hills of Tuscany. After pick-up from the doorstep of your Florence accommodation, your private driver transports you to a vineyard that uses music to age their natural wines. Continue on to Castel Giocondo for a second tasting, followed by a 3-course lunch prepared by Michelin-rated chef Massimo Rossi. Enjoy the meal against a backdrop of the Tuscan countryside.
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  • 6 hours
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  • Free Cancellation
From  
US$620
From  
US$620
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  • 6 hours
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  • Free Cancellation

Siena and Florence Private Tour from LivornoPorts of Call Tours

Siena and Florence Private Tour from Livorno

star-5
When your cruise ship docks in Livorno, benefit from a private full-day tour of Siena and Florence that covers the top attractions efficiently. Drive across Tuscany to see the Duomo in Siena, the Duomo in Florence (Cattedrale di Santa Maria del Fiore), and take a walk across the Ponte Vecchio bridge. Stop into the Mercato del Porcellino to browse their Italian leather goods, before returning to Livorno.
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  • 9 hours
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  • Free Cancellation
From  
US$991
From  
US$991
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  • 9 hours
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  • Free Cancellation


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