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76 results | All Siena Tours

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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
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
$119.26
From
$119.26
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
$83.48
From
$83.48
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
$166.96
From
$166.96
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
$83.48
From
$83.48
Taking safety measures

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
  • Taking safety measures
From
$166.96
From
$166.96
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
$35.78
From
$35.78
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
$153.84
From
$153.84
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
$178.89
From
$178.89
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
$50.09
From
$50.09
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
$155.04
per group
From
$155.04
per group
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
$22.66
From
$22.66
Taking safety measures

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

star-4.5
154
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
$23.02
From
$23.02

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
25
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
  • Taking safety measures
From
$178.89
From
$178.89
Taking safety measures

Guided walking tour of Siena

Guided walking tour of Siena

star-4
13
Siena is a treasure trove of historical, artistic, religious and cultural riches all to be discovered. The best way to do it is on foot, admiring the changes to the town over the centuries and enjoying the spectacular scenery and curious particulars. With an authorized guide you will be able to appreciate the major tourist attractions like Piazza del Campo, the true heart of the town, the Palazzo Comunale (Town Hall), the Cathedral and the majestic Basilica of San Domenico. There will also be no lack of references to the great noble families, such as the Piccolomini, Tolomei and Salimbeni, and their palazzos, to the great tradition of the Siena Palio, but also to the stories of pilgrimage and saintliness that distinguish the town. The walk continues with a visit to the Cathedral that preserves the treasures of artists like Nicola Pisano, Duccio di Buoninsegna, Donatello and Gianlorenzo Bernini, besides its marvelous marble floor, which is a unique example in the history of art.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$23.85
From
$23.85
Taking safety measures

From Siena: Pienza and Montepulciano Wine Tour
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From Siena: Pienza and Montepulciano Wine Tour

star-4.5
34
Taste your way through Tuscany with this full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano and Montalcino.
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  • 9 hours
  • Free Cancellation
  • Taking safety measures
From
$83.48
From
$83.48
Taking safety measures

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
$242.50
Price varies by group size
From
$242.50
Price varies by group size

Small-Group Chianti and San Gimignano Sunset Trip from Siena
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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
$178.89
From
$178.89
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
$237.32
Price varies by group size
From
$237.32
Price varies by group size

Small Group E-Bike Tour from Siena with Wine Tasting and Lunch
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Small Group E-Bike Tour from Siena with Wine Tasting and Lunch

star-5
6
Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena and travel by van into the Chianti hills, where you’ll receive your bike and helmet and will get familiar with the gear. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local winery, where you can enjoy a traditional meal and generous wine tasting.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$178.89
From
$178.89
Taking safety measures

Dinner in the Vineyards from Siena

Dinner in the Vineyards from Siena

star-5
4
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
  • Taking safety measures
From
$89.44
From
$89.44
Taking safety measures

Small-Group Chianti Wine-Tasting and Castles Trip from Siena
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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
$178.89
From
$178.89
Taking safety measures

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! After van transport from Florence, 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
  • Taking safety measures
From
$153.84
From
$153.84
Taking safety measures

Chianti and San Gimignano - 3 Wineries and Lunch

Chianti and San Gimignano - 3 Wineries and Lunch

star-5
21
When visiting Florence, spend a delicious day winery hopping in the renowned Chianti wine region. Visit three of the best estates for tastings of Chianti Classico and other top varietals, plus a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of Tuscany’s best-preserved medieval towns.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$237.32
Price varies by group size
From
$237.32
Price varies by group size
Taking safety measures

500 Vintage Tour: Chianti Roads Experience with Lunch from Florence

500 Vintage Tour: Chianti Roads Experience with Lunch from Florence

star-4.5
16
For a classic Italian experience, cruise through Tuscany’s famous Chianti wine region in a restored vintage Fiat 500! Take the wheel on this self-drive, tag-along adventure from Florence, and feel the freedom of the open road as you wind through a landscape of medieval villas, olive groves and rolling vineyards. Midday, stop at a local winery for an authentic Tuscan lunch and a chance to taste the region’s famous bounty.
More
  • 5 to 6 hours
  • Free Cancellation
  • Taking safety measures
From
$178.89
From
$178.89
Taking safety measures

Filters

What people are saying about Day Trips 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
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
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
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
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
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
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
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
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
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
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
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
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
From Siena: Pienza and Montepulciano Wine Tour
"This area of Tuscany is really beautiful, we've had wonderful wine tasting time with Mario the first vineyard in Montalcino and his cat."..."
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
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
Small Group E-Bike Tour from Siena with Wine Tasting and Lunch
"Dominco was an awesome tour guide. We experienced travel issues getting to the tour on time and he was very accommodating. He made sure that everyone was comfortable on the bikes before leaving for the tour. He set a good pace and stopped to check on the riders along the way. Safety was first. The scenic landscape you ride through was amazing. The one site-seeing stop along the bike ride was at the Certosa di Pontignano Monastery. This was a great stop. We also stopped along the way for scenic views. After the bike ride, we went to Museo and Vina Enoteca Eventi Cucina for lunch and wine tasting. The food was great and Andre, our host, was amazing. The food was sourced locally. After eating lunch, we also stopped at another vineyard for another wine tasting."..."
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
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
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
Chianti and San Gimignano - 3 Wineries and Lunch
"We went with my girlfriend to visit the 3 wineries with Niccolò, he was on time to pick us up at our hotel and drived perfectly. On the way he told us numerous stories about Tuscany. The 3 wineries were different from each other, from the small family winery to the third which is more like a deluxe one, where we had a fantastic lunch. We highly recommend the experience!"..."
star-5
500 Vintage Tour: Chianti Roads Experience with Lunch from Florence
"Excellent tour with Stephano and Dimitri. Thet were really great fun and with their excitement and fun you would never guess they did the tour every day. Lorenzo at the vineyard was so passionate and lovely and the "light lunch" was a fantastic three courses. Delicious!"..."

Frequently Asked Questions