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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
$22.86
From
$22.86
Taking safety measures

Private Tour of Siena Cathedral

Private Tour of Siena Cathedral

star-5
2
Opt for a personalized experience of Siena’s top attraction on a private tour of Siena Cathedral (Il Duomo). With just your private guide and party, you’ll discover easy-to-miss details in the cathedral’s interior and benefit from commentary integral to understanding the statues of Michelangelo and the art inside the Chapel of St. John the Baptist. Plus, booking in advance means you’ll save hours of waiting in line with a skip-the-line admission ticket.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$180.48
per group
From
$180.48
per group
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
36
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
$239.43
Price varies by group size
From
$239.43
Price varies by group size

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
24
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
$180.48
From
$180.48
Taking safety measures

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

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

star-5
35
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
$168.44
From
$168.44
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
$306.81
Price varies by group size
From
$306.81
Price varies by group size
Taking safety measures

Full-Day Chianti Tour by Vespa Scooter

Full-Day Chianti Tour by Vespa Scooter

star-3.5
5
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
  • Taking safety measures
From
$155.21
From
$155.21
Taking safety measures

Cooking Class in Tuscan farmhouse from Siena

Cooking Class in Tuscan farmhouse from Siena

star-5
3
Experience a side of Italy rarely available to visitors when you take a cooking class in the Chianti wine region. During your private session, discover the secrets of Tuscan cuisine, from sauces to tiramisu. After dining on the food you just learned to make, continue on to a vineyard for a complimentary wine tasting and pairing lesson. Round-trip transport from Siena is included for your convenience.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$277.54
Price varies by group size
From
$277.54
Price varies by group size
Taking safety measures

Grape stomping in Tuscan farmhouse

Grape stomping in Tuscan farmhouse

star-4
1
Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills.  Explore a local vinyard with your private guide and discover the wine making process. In addition to living out your Italian dreams of crushing grapes with your bare feet, you’ll also enjoy a wine tasting, along with a homemade lunch.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$258.68
Price varies by group size
From
$258.68
Price varies by group size
Taking safety measures

Horseback Riding tour with lunch and Wine Tasting

Horseback Riding tour with lunch and Wine Tasting

star-5
1
Saddle up to explore the stunning countryside of the Chianti wine region on this private half-day horseback riding tour from Castellina. Suitable for all abilities, you’ll ride through scenic vineyards, olive groves, and medieval villages, and stop along the way for a typical Tuscan lunch and wine and olive oil tastings.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$312.82
Price varies by group size
From
$312.82
Price varies by group size
Taking safety measures

Grape stomping in Tuscan farmhouse from Siena

Grape stomping in Tuscan farmhouse from Siena

star-5
1
Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$318.84
Price varies by group size
From
$318.84
Price varies by group size
Taking safety measures

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

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
$180.48
From
$180.48
Taking safety measures

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
$271.95
Price varies by group size
From
$271.95
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
$276.73
Price varies by group size
From
$276.73
Price varies by group size
Taking safety measures

Tuscany by Electric Bike

Tuscany by Electric Bike

star-2.5
3
Get out of Florence and zip through the Tuscan countryside on an electric bike during this guided tour. See the scenic Chianti region, including olive groves and vineyards, on two wheels without the hassle of navigating. The itinerary includes a stop at a local winery for lunch and a tasting of several wines.
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  • 8 to 9 hours
  • Free Cancellation
  • Taking safety measures
From
$156.41
From
$156.41
Taking safety measures

Montalcino and Montepulciano Wine Tour from Siena

Montalcino and Montepulciano Wine Tour from Siena

Explore the Val d'Orcia Region of Tuscany on a private, full-day tour. Stop in Montepulciano to soak up the history of the medieval town and visit a winery where you taste the region’s wines. Sit down for a traditional Tuscan lunch before continuing on to Pienza, a fifteenth-century village filled with antique shops and known to be the birthplace of Pecorino cheese. Finally stop in Montalcino and tastethe sought after Brunello di Montalcino wines while you admire the vineyards and olive groves.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$457.20
Price varies by group size
From
$457.20
Price varies by group size
Taking safety measures

Montalcino and Montepulciano Private Tour

Montalcino and Montepulciano Private Tour

star-5
1
Explore the beautiful Val d’Orcia just outside of Florence on this private full-day tour. Drive through the rolling countryside to visit the picturesque towns of Montepulciano, Pienza, and Montalcino. Sample wines from local vineyards and sit down to a delicious lunch made with fresh ingredients from the region. Discover the Tuscany that appears in movies and on postcards during this tour and admire the beautiful landscapes.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$457.20
Price varies by group size
From
$457.20
Price varies by group size
Taking safety measures

Bike tour and wine tasting from Siena

Bike tour and wine tasting from Siena

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$312.82
Price varies by group size
From
$312.82
Price varies by group size
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
$300.79
Price varies by group size
From
$300.79
Price varies by group size
Taking safety measures

Private Tour: Montalcino Wine Tasting Experience

Private Tour: Montalcino Wine Tasting Experience

star-5
2
Sip some of Italy's best vino with a private full-day wine tour in Montalcino from Cortona. Visit two wineries to taste the famous Brunello wines produced in this part of Tuscany. Learn what makes Brunello so special from sommeliers and wine experts. Sample a selection of Tuscan meats and cheeses with the wine. Have lunch in a winery and visit either Montalcino or the Sant'Antimo Abbey before the end of the tour.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$329.69
Price varies by group size
From
$329.69
Price varies by group size
Taking safety measures

Exciting ATV tour in the Tuscan countryside

Exciting ATV tour in the Tuscan countryside

star-5
14
Immerse yourself in the Tuscan countryside on a two-hour ATV excursion.  Select a start time that works for you and get a briefing from your private guide.  Test out the ATV until you feel comfortable. Then, enjoy the adrenaline rush as you discover the UNESCO listed Crete Senesi area from Chianti to Val d’Orcia by ATV. Your guide is on hand at all times to offer assistance or answer questions.
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  • 2 hours
  • Free Cancellation
From
$144.38
From
$144.38

Half-day Private Walking Tour of Siena

Half-day Private Walking Tour of Siena

star-5
1
Siena is one of Tuscany’s most picturesque medieval towns and this private walking tour is ideal for first-time visitors or those short on time. Take in the highlights of the UNESCO-listed center, stroll around lively Piazza Del Campo, and admire landmarks such as San Domenico Basilica, Palazzo Tolomei, and Cathedral of Siena.
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  • 3 hours
  • Free Cancellation
From
$309.03
per group
From
$309.03
per group

Horseback Riding Tour with wine tasting from Siena

Horseback Riding Tour with wine tasting from Siena

star-5
1
See the Chianti region’s famous vineyards, olive groves, and medieval villages from an entirely new perspective when you embark on a half-day horseback riding tour. This private tour begins with pickup from your Siena accommodation; travel by car to an area winery, where the adventure begins. Once you’ve become acquainted with your horse, you’ll ride past some of the area’s loveliest scenery. Finish with a traditional Tuscan lunch, plus wine tasting.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$336.89
Price varies by group size
From
$336.89
Price varies by group size
Taking safety measures

Dining experience at a local's home in Siena with show cooking

Dining experience at a local's home in Siena with show cooking

Take a private cooking class with a local chef-instructor at their home during this half-day culinary experience in Siena. Learn to prepare a 4-course Italian meal, then enjoy the lunch or dinner that you helped to make with your host. You’ll also sample a selection of red and white wines from Tuscany.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$102.27
From
$102.27
Taking safety measures

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