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

star-4.5
80
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
$161.12
From
$161.12

Tuscan Hills Horseback Riding Tour from Siena

Tuscan Hills Horseback Riding Tour from Siena

star-4
31
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
$80.56
From
$80.56

Siena Sightseeing Walking Tour with Food Tastings for Small Groups or Private

Siena Sightseeing Walking Tour with Food Tastings for Small Groups or Private

Come and discover Siena and its incomparable historic centre with our morning walk that aims at showing you the main attractions but also discovering some hidden gems. You can understand this wonderful medieval city in many ways and taste some of its best local products.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$69.05
Price varies by group size
From
$69.05
Price varies by group size

Montalcino Castle and Vineyards tour with tasting

Montalcino Castle and Vineyards tour with tasting

star-4
12
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
$31.63
From
$31.63

Walking Tour of Siena with food & Chianti wine

Walking Tour of Siena with food & Chianti wine

star-5
10
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
$51.79
From
$51.79

Private Tour: Secret Siena Walking Tour

Private Tour: Secret Siena Walking Tour

star-5
26
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
$241.68
per group
From
$241.68
per group

Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena

star-5
59
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
$117.12
From
$117.12

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

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

star-5
331
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
$172.63
From
$172.63

Full-Day Winery Tour in Montepulciano with Tasting and Lunch

Full-Day Winery Tour in Montepulciano with Tasting and Lunch

star-5
39
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
$229.02
Price varies by group size
From
$229.02
Price varies by group size

Chianti and Castle Tour from Siena

Chianti and Castle Tour from Siena

star-4.5
54
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
$80.56
From
$80.56

Vespa Tour in Chianti with Lunch from Florence

Vespa Tour in Chianti with Lunch from Florence

star-4.5
35
Explore the beautiful Tuscan countryside in Italian style on an authentic Vespa scooter! Zip along hillside roads past historic villas, medieval villages, olive groves and vineyards. Stop at a local farm and winery for a fresh Tuscan lunch and tasting of Chianti wines. Drive your own Vespa, or ride with an experienced guide if you prefer.
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  • 6 hours
  • Free Cancellation
From
$57.54
From
$57.54

San Gimignano, Chianti, and Montalcino Day Trip from Siena

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
From
$115.09
From
$115.09

Skip the Line: Siena Duomo and City Walking Tour
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Skip the Line: Siena Duomo and City Walking Tour

star-4.5
237
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
$34.53
From
$34.53

Siena Vespa Tour Including Lunch at a Chianti Winery

Siena Vespa Tour Including Lunch at a Chianti Winery

star-5
60
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
$148.46
From
$148.46

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

star-5
38
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
$234.02
Price varies by group size
From
$234.02
Price varies by group size

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

star-4
16
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
$80.56
From
$80.56

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
From
$161.12
From
$161.12

Hot Air Balloon Flight Over Tuscany from Siena

Hot Air Balloon Flight Over Tuscany from Siena

star-4.5
37
There’s only one way to see Tuscany: from above. And the best way to do that is via hot air balloon. This 1-hour hot air balloon flight from Siena takes you above Tuscany to get a breathtaking view of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) as you get a commanding view of the countryside and surrounding ancient villages and towns. Upon landing, enjoy a nice glass of sparkling wine to celebrate the amazing trip through the Tuscan heavens.
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  • 3 hours
  • Free Cancellation
From
$333.75
Price varies by group size
From
$333.75
Price varies by group size

Wine Tour with Wine Tasting in Siena

Wine Tour with Wine Tasting in Siena

star-5
44
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
$82.77
From
$82.77

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
27
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
$172.63
From
$172.63

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

star-4.5
166
The magnificent Duomo of Siena is one of the highlights of Siena’s UNESCO-listed historic center, but its popularity means that you could spend a long time queuing outside. This skip-the-line ticket ensures priority entrance and offers access to the Cathedral, the Piccolomini Library, the Baptistery of San Giovanni, the museum, and the Crypt.
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  • 1 to 2 hours
  • Free Cancellation
From
$22.21
From
$22.21

Best of Siena Guided Walking Tour

Best of Siena Guided Walking Tour

star-4
16
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
From
$21.87
From
$21.87

Dinner in the Vineyards from Siena

Dinner in the Vineyards from Siena

star-5
5
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
$103.58
From
$103.58

Tuscan Cooking Class in Siena
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Tuscan Cooking Class in Siena

star-4.5
42
Get an authentic taste of northern Italy on this 4-hour cooking class in Siena. Led by a local chef, learn how to craft a delicious spread of Tuscan favorites, including bruschetta, crostini and pici, thick, hand-rolled pasta originating in Siena. Afterward, enjoy the fruits of your labor as you savor your creations with your group and a glass of vino. Group size is reserved to 15 to keep this experience as intimate as possible.
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  • 4 hours
  • Free Cancellation
From
$113.94
From
$113.94

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What people are saying about Siena Tours

star-5
Small-Group Montepulciano and Pienza Day Trip from Siena
"Incredible day trip! We couldn’t have had a better guide, the views were phenomenal and the lunch was even better than expected."..."
star-5
Tuscan Hills Horseback Riding Tour from Siena
"We had a great afternoon with our guild riding up and down the hills of Seina. She was fabulous, fun and a great guild. We saw wild life which included sheep. Went through wine and olive fields, walked and ran when we wanted to - Just and great time"..."
star-5
Walking Tour of Siena with food & Chianti wine
"Morad was a fount of knowledge and, since we had been to Siena before, curated our private tour to our interests. We enjoyed it very much!"..."
star-5
Private Tour: Secret Siena Walking Tour
"Claudia is a fantastic tour guide, she is so warm and kind, we learned about so many interesting facts and legends! Thank you Claudia you were amazing, your city is bellisima❤️"..."
star-5
Tuscan Cooking Class in Central Siena
"We had an amazing time during the cooking class. It was easy to follow, but the meal we prepared was unique and delicious. In addition, we learned about the how the dishes we prepared fit into the broader culture of Siena and Tuscany; it was one of our favorite experience during our time in Italy. Highly recommend."..."
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
Full-Day Winery Tour in Montepulciano with Tasting and Lunch
"Fantastic day and we learned so much! Tip notch service and tour. I would recommend this tour to everyone!"..."
star-5
Chianti and Castle Tour from Siena
"Views were beautiful and wines were delicious! The castle was a medieval town and not one massive structure, but it was an enjoyable walk through. Our guide Vicentio was great and the hosts at each vineyard lovely."..."
star-5
Vespa Tour in Chianti with Lunch from Florence
"We had a lovely tourguide named Lucca. We wouldn't have minded a somewhat higher pace than 30km/h. The winetasting and lunch were great!"..."
star-5
San Gimignano, Chianti, and Montalcino Day Trip from Siena
"Our all day tour was cancelled but we were offered a half day wine tasting as an alternative. Duccia was a knowledgeable and enthusiastic guide! We laughed and learned a lot. We visited two very memorable wineries that helped us understand the Brunello wine culture."..."
star-5
Skip the Line: Siena Duomo and City Walking Tour
"Fantastic tour! Our guide was knowledgeable and passionate about this wonderful place (wish I could remember her name!). It was just the right length of tour for our group. Absolutely recommend!"..."
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
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
Half-Day Brunello di Montalcino Wine Tour from Siena
"Tasting the best wines in Tuscany.. our tour guide Carlo was great. He explained in details why the Brunello wines are known for its amazing taste."..."
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
Hot Air Balloon Flight Over Tuscany from Siena
"The balloon flight over the valleys of Tuscany was an exquisite experience of special beauty. The flight was perfectly organised by very professional and friendly guides and provided a quite enchanting overview of Tuscany, sunrise included. Definitely recommended !!!"..."
star-5
Wine Tour with Wine Tasting in Siena
"It was really nice. The wine, the food and the whole event were great. I learnt a lot and appreciated the conversation with the guide. Highly recommend it."..."
star-5
Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
"Alex was a pro. The best guide ever. He explained everything. It wouldn’t be the same without him. The winery owner Andrea showed us nothing but hospitality and kindness. Good food and excellent wine. Worth every euro. Thanks guys."..."
star-5
Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket
"The cathedral was magnificent . The process for skip the line tickets was fine , but would be better if we did not have to redeem voucher . I take many of the Viator tours and most of them voucher is ticket."..."
star-5
Best of Siena Guided Walking Tour
"Traveling by myself, I generally sign up for walking tours in foreign cities. Sylvia was an excellent guide through Siena, including the inside of the Duomo. She is competent, attuned to her specific audience, and entertaining in her presentation and I formal chats."..."
star-5
Dinner in the Vineyards from Siena
"What a wonderful way to experience a boutique winery! The dinner courses were delicious as was the wine (and olive oil and balsamic offerings) We ordered a variety of wines as the price was great and so were the shipping costs, and it arrived home shortly after we did. Our driver/host was so fun and gracious and we loved visiting the walled castle town of Monteriggioni prior to our arrival to the winery. Our tour from Siena joined up with their other tour from Florence so it was a lively evening with fun people."..."
star-5
Tuscan Cooking Class in Siena
"Absolutely amazing Simone was fantastic.. bruschetta, ravioli(stuffed with spinach and ricotta, and mmmmm. Tiramisu..amazing experience in the countryside so friendly and welcoming thank you"..."

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