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How to Spend 3 Days in Siena

How to Spend 3 Days in Siena

Siena is more than just a postcard-perfect medieval hilltown. The UNESCO-listed gem is also the ideal base for exploring Chianti, the Val d’Orcia, and the Crete Senesi—a quintessential Tuscan landscapes dotted with tiny villages and rolling vineyards. Here are a few ways to take in Siena and the surrounding countryside in three days. 

Day 1: Explore the Town

Delve into the rich culture and history of this time-capsule town by devoting the day to exploring Siena’s delights, large and small. Begin your visit with skip-the-line access to the soaring Gothic Siena Duomo. Early morning tickets leave you time to linger in the magnificent church and savor works by Donatello, Michelangelo, and Bernini (and help you avoid the tour-bus crowds that flock to the complex later in the day). 

Afterwards, get to know the medieval center of the city with a walking or Segway tour that touches on its architectural treasures, such as the Piazza del Campo, Palazzo Pubblico, Mangia Tower (Torre del Mangia), and Basilica of San Domenico. Some tours also provide insight into the town’s famous Palio festival with a stroll through thecontrade districts, and most pause in the Piazza del Mercato for photo ops from the scenic overlook and a chance to explore the quiet artisan-lined back streets. 

Day 2: Outside the Walls

Located just outside Siena’s imposing medieval city walls, the undulating Crete Senesi region offers some of the most striking views in Tuscany. Admire this landscape from the air on a hot-air balloon flight or from the ground with a guided hike through the hills. Foodies can combine countryside and cuisine by joining a truffle hunt or a cooking class, and wine lovers can visit the local wineries on a tuk-tuk, all-terrain vehicle, or e-bike winery tour. 

True oenophiles may want to head a bit further afield to sample prestigious Chianti or Brunello di Montalcino wines where they are produced. Opt for a day trip that provides transportation, and you can imbibe with peace of mind. Most wine-tasting tours include stops at a winery or two for tastings as well as free time in the scenic hill towns like Radda, Castellina, or Montalcino and an informal Tuscan lunch.

Day 3: Adventures Across the Border

After exploring the city and its surroundings, take advantage of Siena’s strategic location in the center of Tuscany, and take a day trip to the furthest reaches of the region—or even across the border into Umbria, Liguria, or Emilia-Romagna. Unforgettable Tuscan destinations include the hill towns of San Gimignano, Volterra, and Montepulciano and the scenic streets of Pienza. 

You can also make a break for the Ligurian coast with a guided tour of the fishing villages of Porto Venere and the Cinque Terre and or double-down on art and culture by taking in the frescoed museums and churches of Cortona and Assisi, located on the border between Tuscany and Umbria. Alternatively, you can rev your engines with a guided tour of the Ferrari Museum near Modena and enjoy tastings of local balsamic vinegar and Parmigiano-Reggiano cheese. Then head back to Siena for one last night enjoying the city’s enotecas and wine bars.

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12 Tours and Activities | All Siena Tours

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Hot Air Balloon Flight Over Tuscany from Siena

Hot Air Balloon Flight Over Tuscany from Siena

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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
  • Free Cancellation
  • Taking safety measures
From
$338.10
Price varies by group size
From
$338.10
Price varies by group size
Taking safety measures

Half-Day Brunello di Montalcino Wine Tour from Siena

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
$86.38
From
$86.38
Taking safety measures

Small-Group Montepulciano and Pienza Day Trip from Siena

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
$172.77
From
$172.77
Taking safety measures

Small-Group San Gimignano and Volterra Day Trip from Siena

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
$172.77
From
$172.77
Taking safety measures

Exciting ATV tour in the Tuscan countryside

Exciting ATV tour in the Tuscan countryside

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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
$148.09
From
$148.09

Private Tour: Guided Hike in Tuscany with Transport from Siena

Private Tour: Guided Hike in Tuscany with Transport from Siena

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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
$296.17
Price varies by group size
From
$296.17
Price varies by group size

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

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The magnificent Duomo of Siena is one of the highlights of Siena’s UNESCO-listed historic center, but its popularity means that you could spend a long time queuing outside. This skip-the-line ticket ensures priority entrance and offers access to the Cathedral, the Piccolomini Library, the Baptistery of San Giovanni, the museum, and the Crypt.
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  • 1 to 2 hours
  • Free Cancellation
From
$14.81
From
$14.81

Small Group E-Bike Tour from Siena with Wine Tasting and Lunch

Small Group E-Bike Tour from Siena with Wine Tasting and Lunch

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Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena and travel by van into the Chianti hills, where you’ll receive your bike and helmet and will get familiar with the gear. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local winery, where you can enjoy a traditional meal and generous wine tasting.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$185.11
From
$185.11
Taking safety measures

Half-day Private Walking Tour of Siena

Half-day Private Walking Tour of Siena

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Siena is one of Tuscany’s most picturesque medieval towns and this private 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
  • Free Cancellation
From
$316.96
per group
From
$316.96
per group

Private Tuscany Tuk Tuk Tour Including Lunch and Wine Tasting

Private Tuscany Tuk Tuk Tour Including Lunch and Wine Tasting

Explore the Tuscan countryside from a perspective rare to visitors on an Ape Calessino, a classic Italian buggy used in small villages across the country. In addition to navigating for you, your guide ensures the best views and plenty of photo opportunities along the way. Lunch and three wine tastings are provided to round out the authentic Italian experience.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$321.81
Price varies by group size
From
$321.81
Price varies by group size
Taking safety measures

Siena countryside: cooking class in an exclusive estate

Siena countryside: cooking class in an exclusive estate

Discover Tuscany through its culinary heritage during this hands-on cooking class. Head to an elegant villa in the countryside outside of Siena, and get ready to cook: you’ll be making a complete, multi-course meal of traditional Tuscan dishes, based on what’s in season. With just a small group for company, you’ll receive personal guidance and cooking tips from the chefs. Finish the class by sitting down to the meal you’ve just prepared, served with several glasses of locally made wine.
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  • 3 hours
  • Free Cancellation
From
$238.59
From
$238.59

Siena Segway Tour

Siena Segway Tour

star-3
Mix medieval times with the 21st century on this small-group or private 3-hour tour of Siena via Segway. Gliding around town on two wheels, follow your guide while learning about the history of the town and each place you visit. See this Tuscan town’s main attractions from a Segway, including Piazza del Campo, Piazza del Duomo and Basilica of San Domenico. Get a killer view from the imposing Fortezza Medicea. Opt to take the tour in the morning, afternoon or in the evening to better suit your time in Siena. The number of participants on this small-group tour is limited to just eight, so you’re sure to get plenty of personalized attention from the guide.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$183.85
Price varies by group size
From
$183.85
Price varies by group size
Taking safety measures