Top Siena Private Sightseeing Tours
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118 results | All Siena Tours
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Bike Tour and Wine Tasting from San Gimignano
1
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.
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From
$329.19
Price varies by group size
From
$329.19
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Siena Top 10 Pula Tour
16
Our Polaguides will allow you to discover the most hidden places, but no less fascinating than Siena and instant photography will allow you to appreciate the beauty of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.
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From
$42.60
per group
From
$42.60
per group

Private Tour: Siena Walking Tour
30
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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From
$175.37
per group
From
$175.37
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

VESPA Tour in Tuscany
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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From
$280.42
Price varies by group size
From
$280.42
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Private Tour: Secret Siena Walking Tour
20
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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From
$256.04
per group
From
$256.04
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA
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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From
$275.58
Price varies by group size
From
$275.58
Price varies by group size

Grape stomping in Tuscan farmhouse from Siena
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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From
$323.10
Price varies by group size
From
$323.10
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Private Tour: Guided Hike in Tuscany with Transport from Siena
5
Drench yourself in the fabled Tuscan countryside on this private, day-long hiking tour from Siena. Meet your expert guide in Siena and then drive in a comfortable minivan to the trail where you perambulate through verdant vineyards, rustic villages, and over the classic rolling hills of Tuscany. Stop halfway along the hike to indulge in a classic lunch of Tuscan treats and then travel via minivan to the town of San Gimignano, known as the ‘medieval Manhattan’ for its many gothic towers that form a medieval skyline in the 21st century.
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From
$292.61
Price varies by group size
From
$292.61
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More

The best of Siena - Private Walking Tour
3
Enjoy an interesting stroll around the Tuscan jewel of Siena with this 2-hour private walking tour. See the main attractions of the UNESCO-listed city while getting plenty of personal attention from your private guide.
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From
$170.69
per group
From
$170.69
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Chianti Classico Organic Wine Tour
67
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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From
$534.46
Price varies by group size
From
$534.46
Price varies by group size

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from Florence
3
This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.
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From
$339.15
Price varies by group size
From
$339.15
Price varies by group size

Grape stomping in Tuscan farmhouse
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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From
$262.13
Price varies by group size
From
$262.13
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

E-Bike Tour in Val d'Orcia
9
Pedal through rolling hills and medieval villages in the scenic Val d’Orcia on an e-bike tour that includes lunch and an on-farm cheese tasting. With a guide to select the safest and most scenic bike routes through the UNESCO-listed agricultural region, you can focus on the experience. Provided e-bikes mean this tour can be as challenging—or as relaxed—as you want.
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From
$268.23
Price varies by group size
From
$268.23
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

PolaTour The 17 Fountains of the Contradas of Siena
6
Our Polaguides will allow you to discover the most hidden places, but no less fascinating than Siena and its districts and instant photography will allow you to appreciate the beauties of each district from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.
…More
From
$40.09
per group
From
$40.09
per group

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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From
$317.00
Price varies by group size
From
$317.00
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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- Unique Experiences
- Baptistery of San Giovanni (Battistero di San Giovanni)
- Piccolomini Library (Libreria Piccolomini)
- Montalcino Fortress (Fortezza di Montalcino)
- Palio of Siena (Palio di Siena)
- Santa Maria della Scala
- Siena Historic Center (Siena Centro Storico)
- Siena Cathedral Museum (Museo dell’Opera Metropolitana)
- Fonte Gaia (Gaia Fountain)
- Mangia Tower (Torre del Mangia)
- National Art Gallery of Siena (Pinacoteca Nazionale Siena)
- Things to do in Tuscany
- Things to do in San Gimignano
- Things to do in Chianti
- Things to do in Florence
- Things to do in Livorno
- Things to do in Pisa
- Things to do in Perugia
- Things to do in Lake Bolsena
- Things to do in Assisi
- Things to do in Bologna
- Things to do in Rome
- Things to do in Genoa
- Things to do in Venice
- Things to do in Umbria
- Things to do in Emilia-Romagna