Top Siena Tours, Sightseeing & Cruises
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170 results | All Siena Tours
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Siena Vespa Tour Including Lunch at a Chianti Winery
52
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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From
$156.23
From
$156.23

Small-Group Montepulciano and Pienza Day Trip from Siena
78
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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From
$169.55
From
$169.55
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Skip the Line: Siena Duomo and City Walking Tour
218
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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From
$36.33
From
$36.33
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Small-Group San Gimignano and Volterra Day Trip from Siena
48
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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From
$169.55
From
$169.55
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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San Gimignano, Chianti, and Montalcino Day Trip from Siena
30
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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From
$121.11
From
$121.11
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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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
$42.32
per group
From
$42.32
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
$174.20
per group
From
$174.20
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
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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
$278.55
Price varies by group size
From
$278.55
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

Chianti and Castle Tour from Siena
43
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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From
$84.78
From
$84.78
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Small-Group Chianti and San Gimignano Sunset Trip from Siena
23
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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From
$181.66
From
$181.66
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
$254.33
per group
From
$254.33
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

Best of Siena Guided Walking Tour
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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From
$23.01
From
$23.01
Face masks required for travelers in public areas
Face masks required for guides in public areas
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Siena Historic City Walking Tour with Cathedral Option
41
Discover the treasures of one of the most beautiful cities in the world with a monolingual local guide and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. With a small group you will explore the best that Siena has to offer. Your guide will accompany you along the ancient streets of Siena through the most beautiful sites such as: Piazza del Campo, Palazzo Pubblico, Palazzo Tolomei, Palazzo Salimbeni, the ancient via Banchi di Sopra, the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, the Baptistery and the Cathedral. You will visit also the inside of the Cathedral (ticket not included), if you choose the Cathedral option, where you will admire the works of art of important Italian artists, such as Michelangelo, Donatello and Bernini.
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From
$24.22
From
$24.22
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
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Chianti Wine Tasting and San Gimignano Day Trip from Siena
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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From
$50.87
From
$50.87
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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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
$326.99
Price varies by group size
From
$326.99
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

Off-Road Tuscan Wine Tour from Castellina
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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From
$308.82
Price varies by group size
From
$308.82
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

Small-Group Chianti Wine-Tasting and Castles Trip from Siena
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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From
$169.55
From
$169.55
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

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
22
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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From
$181.66
From
$181.66
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

From Siena: Pienza and Montepulciano Wine Tour
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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From
$66.61
From
$66.61
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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
$290.66
Price varies by group size
From
$290.66
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

Full-Day Winery Tour in Montepulciano with Tasting and Lunch
34
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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From
$241.00
Price varies by group size
From
$241.00
Price varies by group size

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch
26
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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From
$246.26
Price varies by group size
From
$246.26
Price varies by group size

Wine Tour with Wine Tasting in Siena
27
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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From
$87.10
From
$87.10

Dinner in the Vineyards from Siena
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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From
$90.83
From
$90.83
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
- Fonte Gaia (Gaia Fountain)
- National Art Gallery of Siena (Pinacoteca Nazionale Siena)
- Mangia Tower (Torre del Mangia)
- Baptistery of San Giovanni (Battistero di San Giovanni)
- Siena Cathedral Museum (Museo dell’Opera Metropolitana)
- Piccolomini Library (Libreria Piccolomini)
- Siena Historic Center (Siena Centro Storico)
- Santa Maria della Scala
- Montalcino Fortress (Fortezza di Montalcino)
- Palio of Siena (Palio di 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