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Top Siena Day Trips

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We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

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75 Siena Day Trips | All Siena Tours

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Montepulciano Wine Tasting and LunchDay Trips

Montepulciano Wine Tasting and Lunch

star-5
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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  • 1 to 8 hours
  • Free Cancellation
From
$280.48
Price varies by group size
From
$280.48
Price varies by group size

Siena Vespa Tour Including Lunch at a Chianti WineryDay Trips

Siena Vespa Tour Including Lunch at a Chianti Winery

star-5
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
$155.37
From
$155.37

Chianti Wine Tasting and San Gimignano Day Trip from SienaDay Trips

Chianti Wine Tasting and San Gimignano Day Trip from Siena

star-4.5
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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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$50.58
From
$50.58
Taking safety measures

Small-Group Montepulciano and Pienza Day Trip from SienaDay Trips

Small-Group Montepulciano and Pienza Day Trip from Siena

star-4.5
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
  • Taking safety measures
From
$228.84
From
$228.84
Taking safety measures

Chianti and Castle Tour from SienaDay Trips

Chianti and Castle Tour from Siena

star-4.5
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
  • Taking safety measures
From
$84.31
From
$84.31
Taking safety measures

Small-Group San Gimignano and Volterra Day Trip from SienaDay Trips

Small-Group San Gimignano and Volterra Day Trip from Siena

star-5
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
  • Taking safety measures
From
$228.84
From
$228.84
Taking safety measures

San Gimignano, Chianti, and Montalcino Day Trip from SienaDay Trips

San Gimignano, Chianti, and Montalcino Day Trip from Siena

star-4.5
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
  • Taking safety measures
From
$120.44
From
$120.44
Taking safety measures

Half-Day Brunello di Montalcino Wine Tour from SienaDay Trips

Half-Day Brunello di Montalcino Wine Tour from Siena

star-4
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
  • Taking safety measures
From
$84.31
From
$84.31
Taking safety measures

Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery LunchDay Trips

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

star-4.5
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
$180.66
From
$180.66
Taking safety measures

Small-Group Chianti Wine-Tasting and Castles Trip from SienaDay Trips

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

star-5
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
$228.84
From
$228.84
Taking safety measures

From Siena: Pienza and Montepulciano Wine TourDay Trips

From Siena: Pienza and Montepulciano Wine Tour

star-4.5
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
  • Taking safety measures
From
$66.24
From
$66.24
Taking safety measures

Bike Tour and Wine Tasting from San GimignanoDay Trips

Bike Tour and Wine Tasting from San Gimignano

star-5
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
  • Taking safety measures
From
$325.19
Price varies by group size
From
$325.19
Price varies by group size
Taking safety measures

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENADay Trips

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

star-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
From
$272.23
Price varies by group size
From
$272.23
Price varies by group size

Dinner in the Vineyards from SienaDay Trips

Dinner in the Vineyards from Siena

star-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
  • Taking safety measures
From
$90.33
From
$90.33
Taking safety measures

VESPA Tour in TuscanyDay Trips

VESPA Tour in Tuscany

star-5
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
$277.01
Price varies by group size
From
$277.01
Price varies by group size
Taking safety measures

Small-Group Chianti and San Gimignano Sunset Trip from SienaDay Trips

Small-Group Chianti and San Gimignano Sunset Trip from Siena

star-4.5
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
  • Taking safety measures
From
$240.88
From
$240.88
Taking safety measures

Private Tour: Guided Hike in Tuscany with Transport from SienaDay Trips

Private Tour: Guided Hike in Tuscany with Transport from Siena

star-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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  • 7 hours
  • Free Cancellation
From
$289.06
Price varies by group size
From
$289.06
Price varies by group size

E-Bike Tour in Val d'OrciaDay Trips

E-Bike Tour in Val d'Orcia

star-5
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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  • 6 to 7 hours
  • Free Cancellation
From
$264.97
Price varies by group size
From
$264.97
Price varies by group size

Chianti Classico E-Bike TourDay Trips

Chianti Classico E-Bike Tour

star-5
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
$264.97
Price varies by group size
From
$264.97
Price varies by group size

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SienaDay Trips

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Siena

star-5
Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury Mercedes vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.
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  • 8 hours
  • Free Cancellation
From
$272.23
Price varies by group size
From
$272.23
Price varies by group size

Montalcino and Montepulciano Private Tour Day Trips

Montalcino and Montepulciano Private Tour

star-5
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
$457.67
Price varies by group size
From
$457.67
Price varies by group size
Taking safety measures

Bike tour and wine tasting from SienaDay Trips

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
$313.14
Price varies by group size
From
$313.14
Price varies by group size
Taking safety measures

Vespa tour in MaremmaDay Trips

Vespa tour in Maremma

Explore the gorgeous landscape of Maremma while riding a Vespa motorbike on on a half-day tour led by a local guide. Each participant drives a Vespa through this part of southern Tuscany, stopping at landmarks and scenic points along the way. Finish your tour with a Tuscan-style lunch with wine tastings that takes place outdoors overlooking the vineyards.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$481.76
Price varies by group size
From
$481.76
Price varies by group size
Taking safety measures

Brunello di Montalcino wine experience with a sommelier from SienaDay Trips

Brunello di Montalcino wine experience with a sommelier from Siena

star-5
One of the best wine region of the world with a local driving-guide and wine connoisseur, born and raise in the area.Private tour in two boutique wineries , driving through the most scenic road of Val d'Orcia with chance to stop for the best Tuscan countryside pictures.
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  • 5 to 6 hours
  • Free Cancellation
From
$325.19
Price varies by group size
From
$325.19
Price varies by group size

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