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54 results | All Siena Tours

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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
32
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
  • Taking safety measures
From
$119.38
From
$119.38
Taking safety measures

Small-Group San Gimignano and Volterra Day Trip from Siena

Small-Group San Gimignano and Volterra Day Trip from Siena

star-5
49
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
  • Taking safety measures
From
$167.14
From
$167.14
Taking safety measures

Private Tour: Siena Walking Tour

Private Tour: Siena Walking Tour

star-5
33
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
  • Taking safety measures
From
$155.20
per group
From
$155.20
per group
Taking safety measures

Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour

star-4.5
230
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
  • Taking safety measures
From
$35.82
From
$35.82
Taking safety measures

Chianti and Castle Tour from Siena

Chianti and Castle Tour from Siena

star-4.5
48
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
  • Taking safety measures
From
$83.57
From
$83.57
Taking safety measures

Half-Day Brunello di Montalcino Wine Tour from Siena

Half-Day Brunello di Montalcino Wine Tour from Siena

star-4
15
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
  • Taking safety measures
From
$83.57
From
$83.57
Taking safety measures

Best of Siena Guided Walking Tour

Best of Siena Guided Walking Tour

star-4
15
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
  • Free Cancellation
  • Taking safety measures
From
$22.68
From
$22.68
Taking safety measures

Chianti Wine Tasting and San Gimignano Day Trip from Siena

Chianti Wine Tasting and San Gimignano Day Trip from Siena

star-4.5
203
Soak up the local vino and small-town charm of San Gimignano on this wine tasting trip from Siena. Explore San Gimignano first at your leisure, spotting landmarks such as the Collegiata and Pizza del Duomo while strolling the medieval streets. Afterward, travel deeper into the Tuscan hills, and enjoy an intimate winery tour. Sip and swirl Chianti blends with an inside look at the winemaking process.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$50.14
From
$50.14
Taking safety measures

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

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

star-5
325
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
  • Taking safety measures
From
$179.08
From
$179.08
Taking safety measures

Siena Vespa Tour Including Lunch at a Chianti Winery

Siena Vespa Tour Including Lunch at a Chianti Winery

star-5
58
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
  • Taking safety measures
From
$154.01
From
$154.01
Taking safety measures

Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena

star-5
55
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
  • Taking safety measures
From
$121.50
From
$121.50
Taking safety measures

Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

star-5
24
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
  • Taking safety measures
From
$53.72
From
$53.72
Taking safety measures

Chianti Classico Organic Wine Tour

Chianti Classico Organic Wine Tour

star-5
68
Oenophiles will appreciate this tour through Tuscany, which is known for its outstanding Chianti wine. Visit a working vineyard to learn about and sample Chianti Classico, Chianti Riserva and Super Tuscan wines. Take a break to explore a nearby Medieval village, then visit a second farmhouse-style winery to sample more wines and local olive oils.
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  • 7 to 8 hours
  • Free Cancellation
From
$523.33
Price varies by group size
From
$523.33
Price varies by group size

Small-Group Chianti Wine-Tasting and Castles Trip from Siena
Likely to Sell OutLikely to Sell Out

Small-Group Chianti Wine-Tasting and Castles Trip from Siena

star-5
37
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
  • Taking safety measures
From
$179.08
From
$179.08
Taking safety measures

Full-Day Winery Tour in Montepulciano with Tasting and Lunch

Full-Day Winery Tour in Montepulciano with Tasting and Lunch

star-5
38
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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  • 8 hours
  • Free Cancellation
From
$237.57
Price varies by group size
From
$237.57
Price varies by group size

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

star-5
33
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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  • 8 hours
  • Free Cancellation
From
$242.76
Price varies by group size
From
$242.76
Price varies by group size

Small-Group Chianti and San Gimignano Sunset Trip from Siena
Likely to Sell OutLikely to Sell Out

Small-Group Chianti and San Gimignano Sunset Trip from Siena

star-4.5
24
Sip world-class wine and watch the sunset on this day trip to Chianti and San Gimignano from Siena. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills. Group size is reserved for eight people to keep the experience as intimate as possible. 
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  • 8 to 9 hours
  • Free Cancellation
  • Taking safety measures
From
$179.08
From
$179.08
Taking safety measures

Off-Road Tuscan Wine Tour from Castellina

Off-Road Tuscan Wine Tour from Castellina

star-5
11
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
  • Free Cancellation
  • Taking safety measures
From
$304.43
Price varies by group size
From
$304.43
Price varies by group size
Taking safety measures

Siena: Medieval Legends Exploration Game

Siena: Medieval Legends Exploration Game

star-5
8
Discover the city’s historic city center by solving clues and unlocking stories on your phone. Play the engaging exploration game, reenacting the struggle of one of the most important families in Medieval Siena in their fight to gain power. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. And you can play offline. Ready for an adventure? Highlights include: • Admire the pretty fountain of Fonte Gaia, Piazza del Duomo, Palazzo Tolomei and many other local beauties. • Visit the second-oldest bank in the world. • Enjoy a uniquely crafted story brought to you by our talented writers. • Solve clues to find local stories and hidden gems as you explore. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt.
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  • 1 hour to 1 hour 30 minutes
  • Free Cancellation
From
$5.96
Price varies by group size
From
$5.96
Price varies by group size

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
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
  • Free Cancellation
  • Taking safety measures
From
$269.84
Price varies by group size
From
$269.84
Price varies by group size
Taking safety measures

VESPA Tour in Tuscany

VESPA Tour in Tuscany

star-5
4
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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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$274.58
Price varies by group size
From
$274.58
Price varies by group size
Taking safety measures

Private Tour: Tuscany Hot Air Balloon Flight with Transport from Siena

Private Tour: Tuscany Hot Air Balloon Flight with Transport from Siena

star-5
2
Admire the gorgeous landscapes of Tuscany from above on this 1-hour hot air balloon flight from Siena! This thrilling hot air balloon ride takes you up 2,000 feet (609 meters) over the rolling hills, classic Italian villas, imposing castles and sprawling vineyards and olive groves of the Tuscan countryside. Toast to this unforgettable experience with a glass of sparkling wine upon landing.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$2,289.56
From
$2,289.56
Taking safety measures

Truffle Hunting with Wine Tasting in Chianti

Truffle Hunting with Wine Tasting in Chianti

star-5
2
Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$298.46
Price varies by group size
From
$298.46
Price varies by group size
Taking safety measures

Bike Tour and Wine Tasting from San Gimignano

Bike Tour and Wine Tasting from San Gimignano

star-5
2
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
  • Taking safety measures
From
$322.34
Price varies by group size
From
$322.34
Price varies by group size
Taking safety measures

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What people are saying about Private and Luxury in Siena

star-5
San Gimignano, Chianti, and Montalcino Day Trip from Siena
"A really exciting excursion with two wine tastings. Including snack & wonderful insights into the landscape & villages of Tuscany! Really to be recommended! We met exciting people from all over the world at the tastings. Duration (11 hours) was perfect. We were even picked up at the hotel. :)"..."
star-5
Small-Group San Gimignano and Volterra Day Trip from Siena
"Fabulous guide Amber, and small group made this a wonderful tour. Amber was amazing!!!! Highly recommend Tuscan Escapes for all tours in Tuscany."..."
star-5
Private Tour: Siena Walking Tour
"The guide Silvia has broad knowledge of different subjects like architecture, history, local food, people of the city ... and uses it to customize the tour individually to the audience. We have learned a lot about Siena and had a lot of fun. It was a great experience."..."
star-5
Skip the Line: Siena Duomo and City Walking Tour
"Eleanor was excellent - warm, friendly and most welcoming. The tour was brilliant - a great mix of history and local culture. Everything was well explained- we learned loads about the city and were blown away by the stories of the Palio and then the inside of the Duomo . A great overall tour - cdo it tomorrow!"..."
star-5
Chianti and Castle Tour from Siena
"we enjoyed our trip, Francesco guided us very well throught the beautiful landscape of Toscany and the wine was delicious."..."
star-5
Half-Day Brunello di Montalcino Wine Tour from Siena
"We had a GREAT time, learned a lot, ate plenty, and drank PLENTY! Our guide was very knowledgeable about the area and shared that with us. Toured 2 wineries with tastings. Fun afternoon. Highly recommend."..."
star-5
Best of Siena Guided Walking Tour
"Italian guide sharing a lot of her knowledge with obvious pleasure. Detailed information on the town, its history and customs. Definitely worth the price!"..."
star-5
Chianti Wine Tasting and San Gimignano Day Trip from Siena
"Worth experiencing. They covered three main touristic spots near to siena. Wine tasting experience was nice."..."
star-5
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
"It was an amazing day in the Siena countryside. The scenery was fantastic and the three wineries we visited were very good. I had looked forward to this excursion for a long time and it was worth the wait."..."
star-5
Siena Vespa Tour Including Lunch at a Chianti Winery
"It was a wonderful experience riding down the country side. Our guide was very knowledgeable which made the whole tour even better."..."
star-5
Tuscan Cooking Class in Central Siena
"Absolutly gorgeous ! This is the best way to learn about toscan cooking. The teaching is very clear and we learned a lot about the history of each dish. The respect of sanitory conditions was absolutly perfect. I can't wait to cook what I've learned at home ! I deeply recommand this class for all cooking lovers."..."
star-5
Tuscany Hiking Tour from Siena Including Wine Tasting
"The whole experience was fantastic. The hike was incredible and our tour guide, Francesco, was a joy to hike with. The wine tasting was the perfect end to the journey. 10/10 recommend"..."
star-5
Small-Group Chianti Wine-Tasting and Castles Trip from Siena
"Fabulous tour with Daniel, his knowledge and humor were unbelievable. He made our tour so special. Highly recommend Tuscan Escapes for your tours."..."
star-5
Full-Day Winery Tour in Montepulciano with Tasting and Lunch
"We loved this tour! Great wine and great history. City of Montepulcciano was the highlight! We recommend this anyone who likes wine tours and seeing areas outside normal tourist areas!"..."
star-5
Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch
"Amazing! We loved all the wineries and the stop in Pienza!! We were the only two on the tour and it was very engaging!"..."
star-5
Small-Group Chianti and San Gimignano Sunset Trip from Siena
"We loved this tour especially since we were the only two on it. Our guide Elena was wonderful and very knowledgeable. The owners of the winery were great and we loved the wine and food. San Gimignano was beautiful along with the castle. Dinner was out of this world!"..."
star-5
Off-Road Tuscan Wine Tour from Castellina
"This is by far the best tour we took on a 2 week vacation in Italy. Our guide, Gia(?), was very knowledgeable, friendly and welcoming in introducing us to 3 wineries, including a family run winery in which a family style lunch was served. I would definitely recommend this tour."..."
star-5
Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA
"Our driver, Darrio, was excellent. He made time to show us a few extra local places. The lunch at the farm was incredible and possibly the best part."..."
star-5
VESPA Tour in Tuscany
"Such a fun time. Martina and Stefani were the perfect guides. They took us through some beautiful countryside and we visited a couple of small towns that offered great history and fabulous views. I would recommend them to anyone looking for a fun day."..."
star-5
Bike Tour and Wine Tasting from San Gimignano
"This was an incredible day! Our guide, Fillipo, made our day so much fun... he picked us up at the hotel and provided great information on our ride to where we picked up our bikes. The views on the bike ride descending into the valley were spectacular and Fillipo was very encouraging when the "gentle rolling hills" turned out to be a bit steeper than we anticipated. We had a wonderful lunch and wine tastings at a beautiful farm vineyard. Thanks for a great day.."..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
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What are the best Private and Luxury in Siena?
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