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91 results | All Siena Tours

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Chianti and Castle Tour from Siena

Chianti and Castle Tour from Siena

star-4.5
68
Take the stress out of planning a day in Tuscany on this half-day small-group tour of the Chianti wine region from Siena, including transport. Enjoy an air-conditioned ride over to two popular wineries to taste wines and oils locals love. Plus spend some free time in Monteriggioni, and catch a glimpse of the town’s well-known medieval castle.
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  • 5 hours
  • Free Cancellation
From
$88.63
From
$88.63

Wine Tour with Wine Tasting in Siena

Wine Tour with Wine Tasting in Siena

star-5
73
Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group limited to 12 as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier. Plus, a choice of morning or afternoon departure means you can slot this tour into even the busiest of sightseeing schedules.
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  • 3 hours
  • Free Cancellation
From
$78.20
From
$78.20

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

star-5
393
Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this day trip from Siena. Led by an expert guide, travel to the cellars to learn about the production process and meet the locals behind the delicious red wine. Then, pause at a family-run winery for an authentic Tuscan lunch before exploring the village of Montalcino and the abbey of Sant'Antimo. Stop for additional tastings along the way and conclude with transportation back to Siena. Group size is reserved to eight people for a more intimate experience.
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  • 9 hours
  • Free Cancellation
From
$166.84
From
$166.84

Walking Tour of Siena with food & Chianti wine

Walking Tour of Siena with food & Chianti wine

star-5
24
Take a tour of Siena with a local, and get the lowdown on the city that the guidebooks can’t give. In a small group that’s limited to just ten people, you’ll explore Siena by foot to discover the history behind the UNESCO-listed Piazza del Campo and its nearby monuments, and sample classic food from Tuscany with Chianti wine.
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  • 2 hours
  • Free Cancellation
From
$46.92
From
$46.92

Dinner in the Vineyards from Siena

Dinner in the Vineyards from Siena

star-3.5
14
Spend an enchanted evening at a winery estate in Chianti on this half-day tour from Siena. Travel through the scenic landscape of Tuscany to reach the winery estate, then take a tour of the winery, capped off by wine tasting. Afterward, find your seat at a festively decorated table situated in the vineyards for a barbecue dinner accompanied by wine and music.
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  • 5 hours
  • Free Cancellation
From
$93.85
From
$93.85

Tuscany Hiking Tour from Siena Including Wine Tasting
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Tuscany Hiking Tour from Siena Including Wine Tasting

star-5
36
Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.
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  • 4 hours
  • Free Cancellation
From
$46.92
From
$46.92

San Gimignano, Chianti, and Montalcino Day Trip from Siena
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San Gimignano, Chianti, and Montalcino Day Trip from Siena

star-4.5
46
Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.
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  • 11 hours
  • Free Cancellation
From
$104.27
From
$104.27

Private Tour: Siena Walking Tour
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Private Tour: Siena Walking Tour

star-5
43
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
$145.98
per group
From
$145.98
per group

Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena

star-5
90
Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.
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  • 4 hours
  • Free Cancellation
From
$114.70
From
$114.70

Small-Group San Gimignano and Volterra Day Trip from Siena
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Small-Group San Gimignano and Volterra Day Trip from Siena

star-5
61
Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide. 
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  • 8 hours
  • Free Cancellation
From
$166.84
From
$166.84

Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour

star-4.5
260
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
  • Free Cancellation
From
$36.50
From
$36.50

Small-Group Montepulciano and Pienza Day Trip from Siena
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Small-Group Montepulciano and Pienza Day Trip from Siena

star-5
92
Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.
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  • 8 hours
  • Free Cancellation
From
$166.84
From
$166.84

Tuscan Hills Horseback Riding Tour from Siena

Tuscan Hills Horseback Riding Tour from Siena

star-4
37
Giddy up! Traverse the hills of Tuscany via a unique mode of transportation with this guided horseback tour from Siena. Roam the rolling hills, some clad in grapevines, others blanketed with olive groves, as you and your horse calmly explore the region. Pass through rustic villages, all while learning about the history of the place from your guide. See stunning scenery that you would not have had the chance to encounter.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$78.20
From
$78.20

Siena Historic City Walking Tour with Cathedral Option
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Siena Historic City Walking Tour with Cathedral Option

star-5
116
See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$20.85
From
$20.85

Private Tour: Secret Siena Walking Tour
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Private Tour: Secret Siena Walking Tour

star-5
36
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
$218.97
per group
From
$218.97
per group

Vespa Tour Including Lunch at a Chianti Winery from Siena
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Vespa Tour Including Lunch at a Chianti Winery from Siena

star-4.5
80
See the hills of Tuscany in true Italian style with this action-packed day trip on a Vespa scooter from Siena. Set off on your scooter through the Tuscan countryside, your guide leading the way, as you and other scooter-riding participants make your way to a Chianti winery for lunch. Tour the vineyards and cellars, sample some wine and indulge in an antipasto lunch before heading back to Siena.
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  • 8 hours
  • Free Cancellation
From
$134.51
From
$134.51

Half-Day Brunello di Montalcino Wine Tour from Siena
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Half-Day Brunello di Montalcino Wine Tour from Siena

star-4.5
24
Spend an afternoon in the wine town of Montalcino, tasting the prestigious Brunello di Montalcino and learning about wine production. This tour from Siena that tasting of local wine paired with salami and cured meat. Admire views of the Tuscan countryside from the pretty hill town and discover the region’s generations-old winemaking traditions.
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  • 5 hours
  • Free Cancellation
From
$83.42
From
$83.42

Underground Wine tasting in Medieval Cave Siena

Underground Wine tasting in Medieval Cave Siena

star-5
8
Take your Tuscan wine tasting to the next level with this one-of-a-kind experience set in an authentic medieval aqueduct hidden below the historic city center. Settle in among brick vaults and tunnels dug directly into the stone to sip a selection of the top red, white, and rosé wines from the vineyards of Siena and Chianti, paired with local cheese and bruschetta drizzled with virgin olive oil.
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  • 1 hour 15 minutes
  • Free Cancellation
From
$58.39
From
$58.39

Wine tasting at Bossi Castle

Wine tasting at Bossi Castle

star-5
8
Castello di Bossi produces some of the best wines in the world, making the production house one of the most famous among those working in the sector
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  • 1 hour
  • Free Cancellation
From
$31.28
Price varies by group size
From
$31.28
Price varies by group size

Montalcino Castle and Vineyards tour with tasting

Montalcino Castle and Vineyards tour with tasting

star-3.5
14
Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Exploring in a group no larger than 15, discover 600 years of history, including the chapel, the vineyards, and the cellars. Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.
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  • 1 hour
  • Free Cancellation
From
$36.50
From
$36.50

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

star-4.5
6
Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$58.29
From
$58.29

Montalcino: Brunello Wine Tasting Experience
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Montalcino: Brunello Wine Tasting Experience

star-5
4
Sip Tuscan wine in a medieval castle during a tasting session in Montalcino. Hosted by a professional sommelier, the experience ensures you get the lowdown on the wine as you taste it. Enjoy three varietals including a glass of the prestigious Brunello di Montalcino DOCG, along with local bread or breadsticks and olive oil.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$26.07
From
$26.07

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

star-4.5
31
See Tuscany in classic Italian style by exploring the rustic region via a vintage Fiat 500, the classic, beloved and diminutive Italian automobile. Get picked up at your hotel in Siena and then ride to the stunning hilltop town of Monteriggioni, cruising through the rolling hills of Chianti along the way. Stop at a local vineyard and sample some delicious Italian wines with a hearty lunch of local fare. Follow the guide in a caravan. The number of participants on this small-group tour is limited to just ten, so you’re sure to get plenty of personalized attention from the guide.
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  • 8 hours
  • Free Cancellation
From
$156.41
From
$156.41

Semi Private Chianti Tour from Siena

Semi Private Chianti Tour from Siena

star-5
8
Discover the history of the Chianti region, visit Monteriggioni (a medieval castle and fortress), and stop by a boutique family-owned winery on this tour from Siena. Taste four different Chianti Classico wines paired with delicious Pecorino cheese, bruschetta, salame, and olive oil. Explore the historic cellar and learn about the wine production process.
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  • 3 hours 30 minutes
  • Free Cancellation
From
$72.99
From
$72.99

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