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Top Siena Outdoor Activities

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30 Tours and Activities

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Wine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Castellina

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  
US$ 179.70
From  
US$ 179.70
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  • 4 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Educational Wine Tour & Tasting in Siena

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  
US$ 73.00
From  
US$ 73.00
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  • 3 hours
  • Free Cancellation

Horseback Riding

Tuscan Hills Horseback Riding Tour from Siena

Giddy up! Traverse the hills of Tuscany via a unique mode of transportation with this 2.3-hour 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. Follow the Via Francigena, an ancient pilgrimage route, and 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  
US$ 78.62
From  
US$ 78.62
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  • 2 hours 30 minutes
  • Free Cancellation

City Tours

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
From  
US$ 146.01
From  
US$ 146.01
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  • 6 hours
  • Free Cancellation

Day Trips

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

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  
US$ 95.47
From  
US$ 95.47
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  • 8 hours
  • Free Cancellation

Hiking & Camping

Tuscany Hiking Tour from Siena Including Wine Tasting

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route, about 5 miles (8 km), takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the village of Monteriggioni, one of the most gorgeous hill towns you’ll ever step foot in, you’ll be rewarded with a wine tasting. At the end, head back to Siena via train.
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  • 4 hours
  • Free Cancellation
From  
US$ 50.54
From  
US$ 50.54
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  • 4 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Truffle Hunting in Siena

Discover the art of truffle hunting firsthand on a private 2-hour tour in the morning or evening. Benefit from the expertise of your local guide and his dogs as you learn about the secrets of finding truffles, training the dogs, and culinary uses for the celebrated mushrooms. Finish the tour by tasting truffle products in central Sienna, or opt to stay for a meal (own expense) that features the fresh truffles.
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  • 2 hours
  • Free Cancellation
From  
US$ 73.00
From  
US$ 73.00
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  • 2 hours
  • Free Cancellation

Wine Tasting & Winery Tours

NEW TO VIATOR

Wine and Horses

Among the experiences that can be booked, this that we propose has the particularity of combining a horseback excursion with the tasting of poetry, which this nature, unique in the world, gives to the wines of this land, appreciated all over the world for their high quality, everything, in a naturalistic setting of rare beauty.
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  • 1 day
  • Free Cancellation
From  
US$ 247.09
From  
US$ 247.09
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  • 1 day
  • Free Cancellation

Day Trips

Bike tour and wine tasting from San Gimignano

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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  • 6 hours
  • Free Cancellation
From  
US$ 151.62
From  
US$ 151.62
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  • 6 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Exciting ATV tour in the Tuscan countryside

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  
US$ 123.54
From  
US$ 123.54
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  • 2 hours
  • Free Cancellation

Hiking & Camping

Private Tour: Guided Hike in Tuscany with Transport from Siena

Drench yourself in the fabled Tuscan countryside with 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’ll 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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  • 7 hours
  • Free Cancellation
From  
US$ 116.80
From  
US$ 116.80
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  • 7 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Truffle Hunting with Wine Tasting in Tuscan farmhouse

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
From  
US$ 134.77
From  
US$ 134.77
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  • 4 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Off Road Wine Tour in Chianti Valley from Siena

Explore Chianti’s backroads and beautiful vistas while traveling in a vintage SUV. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste plenty of famous Chianti wine along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a gourmet picnic lunch at a scenic family estate.
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  • 5 hours
  • Free Cancellation
From  
US$ 241.47
From  
US$ 241.47
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  • 5 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Chianti

Go off-road in a vintage SUV on this Chianti Valley tour from Greve. With a small group of just eight people or fewer, travel through the famous wine-producing region to learn the vintners' secrets. Stop at three cellars for 15 tastings of different varietals as well as local products (olive oil, honey) and a traditional Italian lunch.
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  • 4 hours
  • Free Cancellation
From  
US$ 202.16
From  
US$ 202.16
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  • 4 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Off Road 4WD wine tour

This personalized wine tour of Tuscany takes you off-road through the scenic landscapes outside Florence. Set off with your own private party into the Chianti wine region aboard a 4WD vehicle, and indulge in the ultimate wine-and-dine experience. You’ll visit two prominent wineries for seven wine tastings, food pairings, and lunch.
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  • 5 hours
  • Free Cancellation
From  
US$ 140.39
From  
US$ 140.39
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  • 5 hours
  • Free Cancellation

Historical & Heritage Tours

NEW TO VIATOR

PolaTour Top10 Siena

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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  • 60 to 240 minutes
  • Free Cancellation
From  
US$ 33.69
From  
US$ 33.69
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  • 60 to 240 minutes
  • Free Cancellation

Private Sightseeing Tours

Vintage Spider tour in Tuscany

The Spider Tour experience is especially designed for those who want to enjoy the treasures of Chianti on a vintage roadster, a car for true connoisseurs. The car is compact, stylish and extremely comfortable, a model still used in many films and television commercials, which in the 60s was at the height of its success.- Private Tour for couples and small groups- Departure from your location on request- Third-part Insurance- Visit of a typical village + Visit to a winery- Typical tuscan lunch + 3 wine tastings- Return to an agreed meeting point- About 6 hours tour- Languages: Italian, English and Spanish 
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  • 6 hours
  • Free Cancellation
From  
US$ 432.40
From  
US$ 432.40
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  • 6 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Exciting Wine Tasting ATV tour in the Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia
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  • 4 hours
  • Free Cancellation
From  
US$ 235.86
From  
US$ 235.86
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  • 4 hours
  • Free Cancellation

Balloon Rides

NEW TO VIATOR

Private Tour: Tuscany Hot Air Balloon Flight with Transport from Siena

Admire the gorgeous landscapes of Tuscany from above on this 1-hour hot air balloon flight from Siena! This thrilling hot air balloon ride takes you up 2,000 feet (609 meters) over the rolling hills, classic Italian villas, imposing castles and sprawling vineyards and olive groves of the Tuscan countryside. Toast to this unforgettable experience with a glass of sparkling wine upon landing.
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  • 2 hours 30 minutes
  • Free Cancellation
From  
US$ 1,965.46
From  
US$ 1,965.46
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  • 2 hours 30 minutes
  • Free Cancellation

Day Trips

NEW TO VIATOR

From Montepulciano to Pienza by E-bike

An extraordinary tour! We will be at the Chiusi train station, easily reachable by car or train from both Rome and Florence. From there we will start towards Montepulciano, called the "pearl of the sixteenth century". Then we will continue towards the ancient Temple of San Biagio, a Tuscan sixteenth-century masterpiece. We will pass by characteristic white roads immersed in the trees and we will arrive at the medieval village of Montichiello whose origins are lost over time. After a brief refreshment we will leave and in front of our eyes really beautiful landscapes will open up. Then we will arrive in Pienza, a small and charming village known as the "ideal" city of the Renaissance. Here we will have a break lunch tasting typical and genuine foods. Then we will return to Montepulciano through vineyards and olive groves. From arrival to departure the group will have a guide available. The tour will be performed on E-bikes with assisted pedaling.
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  • 7 hours 15 minutes
From  
US$ 88.73
From  
US$ 88.73
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  • 7 hours 15 minutes

4WD, ATV & Off-Road Tours

The knights who freed Val d Orcia from Ghino di Tacco robberies (VIP)

PASSIONSMichele is glad to share with you his passion for bike tours, photography, places of history, nature and cooking.WE WARMLY WELCOMEFamilies and individuals, bike riding lovers, nature fans, people interested in legends and appreciators of good Tuscany cooking. This tour suits people trained at middle level in bike riding.minimum booking available: from 2 people
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  • 7 hours
  • Free Cancellation
From  
US$ 125.79
From  
US$ 125.79
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  • 7 hours
  • Free Cancellation

Nature & Wildlife

NEW TO VIATOR

Carriage Rides Maremma

This amazing tour is located inside of "Parco della Maremma" (natural reserve park) where it is possible to make carriage horse-routes. They will lead you to discover the most fascinating places in the Park. Particularly suggestive is at the sunset an ideal moment to meet the animals that inhabit the Reserve like roe deer, wild boars, foxes. Every routes end with a pleasant tasting on the beach to taste the typical products at km 0 of the farm. The carriage route itinerary is suitable from 0 to 100 years and can be organized on timetables, stops and personalized routes. This private tour includes tickets entrance fee, tasting, guide and naturally round trip trasnfer with carriage. Please bring a valid form of ID/ passport, as visitors may be asked for security reasonsPlease bring sun hat; sun bath; sun towel, sun glasses, confortable shoes
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  • 3 hours
  • Free Cancellation
From  
US$ 393.09
From  
US$ 393.09
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  • 3 hours
  • Free Cancellation

Cultural Tours

NEW TO VIATOR

Siena Running Tour

Siena Running Tour is a new way of visiting the city by exploiting the potential of running and combining fitness and culture. Visitors will have the opportunity to cover a geographical space wider than what you can usually see with a classic visit on foot and enjoy unaspected views. The starting point is the Fortezza Medicea, a traditional Sienese fitness place, from which your guide will give you a wide introduction to the history of the city, taking advantage of the spectacular view of the Cathedral, of the Torre del Mangia, of the ancient hospital of Santa Maria della Scala, in short, of the most important monuments of Siena, as well as, of course, of the fortress itself. Then we will proceed towards the city center, the Market square, ending the tour in Piazza Salimbeni, historical site of the Monte dei Paschi di Siena bank.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
US$ 179.70
From  
US$ 179.70
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  • 1 hour 30 minutes
  • Free Cancellation

Wine Tasting & Winery Tours

NEW TO VIATOR

Hike & Taste experience from Siena

A special hike, a walk that will help you enjoy the city of Siena and reach a winery very close to the city center!
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  • 8 hours
  • Free Cancellation
From  
US$ 99.96
From  
US$ 99.96
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  • 8 hours
  • Free Cancellation


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(888) 651-9785
(888) 651-9785