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100 results | All Siena Tours

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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
$165.24
From
$165.24

Siena Vespa Tour Including Lunch at a Chianti Winery
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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
$152.26
From
$152.26

Chianti and Castle Tour from Siena

Chianti and Castle Tour from Siena

star-4.5
50
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
$82.62
From
$82.62

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
$165.24
From
$165.24

Wine Tour with Wine Tasting in Siena

Wine Tour with Wine Tasting in Siena

star-5
40
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
$84.89
From
$84.89

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
38
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
$177.05
From
$177.05

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
$234.88
Price varies by group size
From
$234.88
Price varies by group size

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
$342.29
Price varies by group size
From
$342.29
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
36
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
$240.01
Price varies by group size
From
$240.01
Price varies by group size

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
$152.26
From
$152.26

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
From
$82.62
From
$82.62

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
From
$118.03
From
$118.03

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
$177.05
From
$177.05

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
From
$177.05
From
$177.05

Private Tour: Secret Siena Walking Tour

Private Tour: Secret Siena Walking Tour

star-5
24
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
$247.87
per group
From
$247.87
per group

Chianti and San Gimignano - 3 Wineries and Lunch

Chianti and San Gimignano - 3 Wineries and Lunch

star-5
23
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
From
$234.88
Price varies by group size
From
$234.88
Price varies by group size

500 Vintage Tour: Chianti Roads Experience with Lunch from Florence

500 Vintage Tour: Chianti Roads Experience with Lunch from Florence

star-4.5
17
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.
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  • 5 to 6 hours
  • Free Cancellation
From
$177.05
From
$177.05

Half-Day Brunello di Montalcino Wine Tour from Siena

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
$82.62
From
$82.62

Off-Road Tuscan Wine Tour from Castellina
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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
From
$300.98
Price varies by group size
From
$300.98
Price varies by group size

Chianti Classico E-Bike Tour

Chianti Classico E-Bike Tour

star-5
9
Get an extra boost from your electric bike on a half-day bike tour of the Chianti region. Follow your guide through a picturesque landscape of gentle hills with vineyards, olive groves, and small villages, stopping at a 12th-century castle and a winery. Your tour includes a wine tasting, bottled water, and use of all necessary equipment.
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  • 6 to 7 hours
  • Free Cancellation
From
$259.67
Price varies by group size
From
$259.67
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
7
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
From
$266.79
Price varies by group size
From
$266.79
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
From
$177.05
From
$177.05

Full-Day Chianti Tour by Vespa Scooter
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Full-Day Chianti Tour by Vespa Scooter

star-3.5
6
Hop on a scooter to explore the rolling landscapes of Chianti on this 7.5-hour Vespa tour from San Gimignano. Settle on a Vespa and ride around vine-coated hills, cypress groves and old villages, soaking in the views of this famous wine producing region. Your tour includes a wine tasting and lunch, plus the option to ride as a passenger with an escort driver or to upgrade to drive your Vespa.
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  • 7 hours 30 minutes
  • Free Cancellation
From
$152.26
From
$152.26

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
$106.23
From
$106.23

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