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51 Siena Half-day Tours

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You can reserve your spot today and pay when you're ready.Learn more

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
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  • Free Cancellation
From  
US$79.05 
From  
US$79.05 
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  • 5 hours
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  • Free Cancellation

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
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  • Free Cancellation
From  
US$47.43 
From  
US$47.43 
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  • 5 hours
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  • Free Cancellation

Off Road 4WD wine tour 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
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  • Free Cancellation
From  
US$271.04 
Price varies by group size
From  
US$271.04 
Price varies by group size
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  • 5 hours
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  • Free Cancellation

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Hot Air Balloon Flight Over Tuscany from SienaHalf-day Tours

Hot Air Balloon Flight Over Tuscany from Siena

star-4.5
There’s only one way to see Tuscany: from above. And the best way to do that is via hot air balloon. This 1-hour hot air balloon flight from Siena takes you above Tuscany to get a breathtaking view of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) as you get a commanding view of the countryside and surrounding ancient villages and towns. Upon landing, enjoy a nice glass of sparkling wine to celebrate the amazing trip through the Tuscan heavens.
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  • 3 hours
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  • Free Cancellation
From  
US$282.33 
Price varies by group size
From  
US$282.33 
Price varies by group size
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  • 3 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouseWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse

star-4
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
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  • Free Cancellation
From  
US$242.81 
Price varies by group size
From  
US$242.81 
Price varies by group size
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  • 4 hours
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  • Free Cancellation

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
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  • Free Cancellation
From  
US$79.05 
From  
US$79.05 
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  • 5 hours
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  • Free Cancellation

Wine tour with a SommelierDay Trips

Wine tour with a Sommelier

Take an in-depth tour of the Tuscan wine regions with a certified expert. Your private guide on this journey is a sommelier who is very familiar with the wines and wineries of the area. Spend the day touring two or three wineries, with samplings at each. A delicious Italian lunch at an organic farm is also included. No need to worry about a designated driver, as pickup and drop-off can be included.
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  • 5 hours
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  • Free Cancellation
From  
US$265.39 
Price varies by group size
From  
US$265.39 
Price varies by group size
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  • 5 hours
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  • Free Cancellation

Off-Road Tuscan Wine Tour from Castellina Dining Experiences

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Off-Road Tuscan Wine Tour from Castellina

star-5
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
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  • Free Cancellation
From  
US$257.49 
US$271.04
US$13.55 savings
Price varies by group size
From  
US$257.49 
US$271.04
US$13.55 savings
Price varies by group size
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  • 4 hours
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  • Free Cancellation

Private Tour: Secret Siena Walking TourHalf-day Tours

Private Tour: Secret Siena Walking Tour

star-5
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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  • 3 hours
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  • Free Cancellation
From  
US$237.16 
per group
From  
US$237.16 
per group
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  • 3 hours
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  • Free Cancellation

Educational Wine Tour & Tasting in SienaWine Tasting & Winery Tours

Educational Wine Tour & Tasting in Siena

star-5
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
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  • Free Cancellation
From  
US$73.41 
From  
US$73.41 
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  • 3 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from FlorenceWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse from Florence

star-5
Get ankle deep in Tuscan tradition on a half-day grape stomping tour from Florence.  Private transportation will take you from your hotel to a winery in the Chianti hills. There, you’ll explore the history and modern practices of winemaking. After tromping on the locally grown grapes, replenish your strength with a homemade lunch and wine tasting, before returning to your accommodation.
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  • 3 hours
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  • Free Cancellation
From  
US$282.33 
Price varies by group size
From  
US$282.33 
Price varies by group size
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  • 3 hours
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  • Free Cancellation

Montalcino and Montepulciano Wine Tour from SienaDay Trips

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
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  • Free Cancellation
From  
US$463.03 
Price varies by group size
From  
US$463.03 
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  • 6 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from SienaWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse from Siena

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
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  • Free Cancellation
From  
US$287.98 
Price varies by group size
From  
US$287.98 
Price varies by group size
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  • 4 hours
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  • Free Cancellation

Private Pienza and Montepulciano Half-Day Trip from SienaHalf-day Tours

Private Pienza and Montepulciano Half-Day Trip from Siena

star-5
Discover the beauty of the Tuscan Val d'Orcia region on a day trip to Pienza and Montepulciano with your own private driver. After leaving Siena, you'll travel through the village of Buonconvento and then into the idyll of gentle hills and stone hamlets that typify the Tuscan landscape. Spend time in Pienza, exploring its artisan shops and trying its famous pecorino cheese, then continue to medieval Montepulciano for a winery visit and tasting.
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  • 6 hours
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  • Free Cancellation
From  
US$271.04 
Price varies by group size
From  
US$271.04 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

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
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  • Free Cancellation
From  
US$429.15 
Price varies by group size
From  
US$429.15 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Private VESPA Tour in TuscanyDay Trips

Private 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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  • 6 hours
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  • Free Cancellation
From  
US$338.80 
Price varies by group size
From  
US$338.80 
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  • 6 hours
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  • Free Cancellation

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
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  • Free Cancellation
From  
US$237.16 
Price varies by group size
From  
US$237.16 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Private Tour in Val d'OrciaDay Trips

Private Tour in Val d'Orcia

Discover the natural beauty of Italy's Val d'Orcia on this private tour that introduces you to the postcard-perfect scenery of rolling hills and vineyards. You'll visit the towns of Montepulciano, Pienza, and Montalcino; tour a winery; and enjoy included wine tastings and a Tuscan lunch for a well-rounded experience in this UNESCO World Heritage–listed valley.
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  • 6 hours
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  • Free Cancellation
From  
US$451.73 
Price varies by group size
From  
US$451.73 
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  • 6 hours
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  • Free Cancellation

Half-day Private Walking Tour of SienaHalf-day Tours

Half-day Private Walking Tour of Siena

star-5
Siena is one of Tuscany’s most picturesque medieval towns and this private 3-hour 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
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  • Free Cancellation
From  
US$282.33 
per group
From  
US$282.33 
per group
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  • 3 hours
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  • Free Cancellation

Bike tour with wine tastingDay Trips

Bike tour with wine tasting

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair, includes hotel pickup and drop-off, and finishes with a lunch of Tuscan dishes and wine.
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  • 6 hours
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  • Free Cancellation
From  
US$225.87 
Price varies by group size
From  
US$225.87 
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  • 6 hours
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  • Free Cancellation

Luxury Montalcino wine tourDay Trips

Luxury Montalcino wine tour

Discover the fine wines of Montalcino, a small town nestled in the hills of Tuscany. After pick-up from the doorstep of your Florence accommodation, your private driver transports you to a vineyard that uses music to age their natural wines. Continue on to Castel Giocondo for a second tasting, followed by a 3-course lunch prepared by Michelin-rated chef Massimo Rossi. Enjoy the meal against a backdrop of the Tuscan countryside.
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  • 6 hours
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  • Free Cancellation
From  
US$621.14 
Price varies by group size
From  
US$621.14 
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  • 6 hours
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  • Free Cancellation

Luxury Maremma wine tourDay Trips

Luxury Maremma wine tour

Get to know the off-the-beaten-path wine region of Maremma, in coastal Tuscany, during this private tour. Round-trip private transportation is convenient and means that you can taste as much wine as you wish. Visit two wineries, both known for their modern architecture, to taste samples and learn about wine production. You'll also enjoy a 3-course lunch and wine pairing.
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  • 6 hours
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  • Free Cancellation
From  
US$643.72 
Price varies by group size
From  
US$643.72 
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  • 6 hours
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  • Free Cancellation

Private Montalcino and Montepulciano Tour from SienaDay Trips

Private Montalcino and Montepulciano Tour from Siena

Travelling in Val d'Orcia is an unforgettable experience. Your eyes become dazzled by the beauty of the colours of this land, unsurprisingly a UNESCO World Heritage Site. This tour has been created for you to discover the most painted corner of Tuscany, made of enchanted landscapes, tree-lined avenues. Sunrises and sunsets of extraordinary, unique colours in the world are one great addition when wandering the road from Montepulciano to Montalcino through Pienza, considered one of the most amazing routes of Italy.
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  • 6 hours
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  • Free Cancellation
From  
US$429.15 
Price varies by group size
From  
US$429.15 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Truffle Hunting with Wine Tasting in Tuscan farmhouseWine Tasting & Winery Tours

Truffle Hunting with Wine Tasting in Tuscan farmhouse

star-5
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
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  • Free Cancellation
From  
US$259.75 
Price varies by group size
From  
US$259.75 
Price varies by group size
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  • 4 hours
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  • Free Cancellation


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