Siena Private Sightseeing Tours
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118 results | All Siena Tours

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Private Tour: Secret Siena Walking Tour

Private Tour: Secret Siena Walking Tour

star-5
47
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
$273.75
per group
From
$273.75
per group

Siena 3h Private Tour

Siena 3h Private Tour

star-4.5
130
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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  • 3 hours
  • Free Cancellation
From
$142.35
Price varies by group size
From
$142.35
Price varies by group size

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

star-5
5
Experience the best of Tuscany—cheese and wine, of course!—on this private tour from Siena. You’ll admire fabulous scenery in the Val d’Orcia, learn about cheese making during a tour at an organic dairy farm, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine during a cellar tour at a winery in the hilltop town of Montalcino. With a privately guided tour, enjoy a more personalized experience.
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  • 8 hours
  • Free Cancellation
From
$766.49
per group
From
$766.49
per group

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
26
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
From
$481.80
Price varies by group size
From
$481.80
Price varies by group size

Private Tour: Siena Walking Tour

Private Tour: Siena Walking Tour

star-5
45
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
$164.25
per group
From
$164.25
per group

Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour

star-5
294
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
$38.32
From
$38.32

San Gimignano, Chianti, and Montalcino Day Trip from Siena
Likely to Sell OutLikely to Sell Out

San Gimignano, Chianti, and Montalcino Day Trip from Siena

star-4.5
56
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
$120.45
From
$120.45

Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena

star-5
116
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
$125.92
From
$125.92

Chianti and Castle small group Tour from Siena with Wine Tasting
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Chianti and Castle small group Tour from Siena with Wine Tasting

star-4.5
76
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
$93.07
From
$93.07

Best of Siena Guided Walking Tour

Best of Siena Guided Walking Tour

star-4
17
Maximize time in Siena with a guided walking tour through the medieval city streets. Starting from the Basilica of San Domenico, pass through Piazza del Campo and see the Palazzo Pubblico (Town Hall). Then, head to the Cathedral to admire its architecture and the beautiful polychrome marble. Upgrade your experience to include a guided tour of the cathedral's interior.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$22.99
From
$22.99

Half-Day Brunello di Montalcino Wine Tour from Siena

Half-Day Brunello di Montalcino Wine Tour from Siena

star-4.5
35
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 30 minutes
  • Free Cancellation
From
$98.55
From
$98.55

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
455
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
$175.20
From
$175.20

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
70
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
$175.20
From
$175.20

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

star-4.5
32
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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  • 7 hours 30 minutes
  • Free Cancellation
From
$164.25
From
$164.25

Wine Class - Tuscan Classics

Wine Class - Tuscan Classics

star-5
250
Tuscany is known for its excellent vintages, but the world of Tuscan wine can be overwhelming for a novice. With this informal wine class, you’ll get your bearings and learn to recognize the most important and storied wines of Tuscany. Delve into the history of Tuscany’s wine production, discover the different wine-producing areas and grapes, and sample a number of reds and whites from the region.
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  • 2 hours
  • Free Cancellation
From
$65.70
From
$65.70

Guided Walking tour of Siena

Guided Walking tour of Siena

star-3.5
21
Siena has one of the most intact medieval cityscapes in Italy and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, town hall, and Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.
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  • 2 hours
  • Free Cancellation
From
$43.80
From
$43.80

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

star-5
40
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
$54.75
From
$54.75

Dinner in the Vineyards from Siena

Dinner in the Vineyards from Siena

star-3.5
18
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
$114.97
From
$114.97

Vespa Tour with Lunch&Chianti Winery from Siena
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Vespa Tour with Lunch&Chianti Winery from Siena

star-4.5
86
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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  • 7 hours 30 minutes
  • Free Cancellation
From
$141.25
From
$141.25

Small-Group Chianti Wine-Tasting Trip from Siena

Small-Group Chianti Wine-Tasting Trip from Siena

star-5
44
Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.
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  • 8 hours
  • Free Cancellation
From
$175.20
From
$175.20

Wine Tour with Wine Tasting in Siena

Wine Tour with Wine Tasting in Siena

star-5
103
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
$82.12
From
$82.12

Tuscan Hills Horseback Riding Tour from Siena
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Tuscan Hills Horseback Riding Tour from Siena

star-4
39
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
$82.12
From
$82.12

Monteriggioni, San Gimignano and Chianti - Day Tour from Siena

Monteriggioni, San Gimignano and Chianti - Day Tour from Siena

star-4.5
2
See more of Tuscany with a private guide, and book a day trip to Monteriggioni, San Gimignano, and Chianti for your personal group of family or friends. After a pickup direct from your Siena hotel, you’ll travel by private vehicle into Tuscany to spend free time in the hill towns of Monteriggioni and San Gimignano. Hear tales of Tuscany’s history as you travel, and then return to Siena via Chianti, where a stop can be made for lunch or even a wine tasting (both own expense).
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  • 6 hours
  • Free Cancellation
From
$514.65
per group
From
$514.65
per group

Private Guided Tour of Siena with a Licensed Local Tour Guide

Private Guided Tour of Siena with a Licensed Local Tour Guide

star-5
6
Siena is one of the most intact medieval towns in Italy, rich in art and architecture. Visit its highlights in just a few hours with this walking tour through the old town. Follow your guide to admire the Duomo and Piazza del Campo, marvel at the Churches of St. Dominic and St. Catherine of Siena, and wander through the historic warren of narrow lanes and quiet squares.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$164.25
per group
From
$164.25
per group

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