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How to Spend 2 Days in Siena

How to Spend 2 Days in Siena

Discover one of Tuscany’s best preserved medieval towns in the historic city center of Siena, a UNESCO World Heritage Site. Then, pair those urban piazzas with scenic countryside as you explore the surrounding wine country of Chianti and Val d’Orcia. Here are your best options for spending two days in Siena.

Day 1: Siena, Inside and Out

**Morning:**Begin your day by getting to know the Siena Cathedral (Duomo di Siena) from top to bottom. Beat the crowds by booking skip-the-line tickets so you don’t have to wait to enter the complex and can take your time exploring the Gothic church, crypt, baptistry, museum, and Piccolomini Library. 

**Afternoon:**From Siena’s soaring cathedral, move on to its medieval historic center, centered around the Piazza del Campo. Join a private walking tour to take in all the town highlights in just a few hours, from the imposing Palazzo Pubblico and Torre del Mangia to the cobbled lanes lined with shops.

**Night:**After a day of art and architecture, it’s time to unwind with an evening of food and wine. An informal cooking class or wine tasting workshop offers a hands-on way to learn about—and sample—Tuscany’s regional cuisine and cap off your first day in Siena.

Day 2: Wine, Crafts, and Views

**Morning:**You’ve seen the sights in town, now head for the hills. Join a wine-tasting day trip to Montalcino or San Gimignano, or travel by Vespa scooter or vintage Fiat 500 to the wineries just outside Siena. Outdoor enthusiasts can join a hiking or e-bike wine tour with tastings and lunch.

**Afternoon:**Siena is famous for its prestigious wine, traditional crafts, and fairytale scenery. You’ve crossed wine off the list, so devote the afternoon to learning the history of majolica production with a ceramics workshop, or join a guided photography tour to capture choice shots of the town and its views.

**Night:**Make your final evening memorable by watching the sun set over the medieval old town and rolling countryside beyond. Head to the panoramic Piazza del Mercato with a night tour, or climb to the top of the Torre del Mangia for sweeping views across the Sienese hills.

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9 Tours and Activities | All Siena Tours

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

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Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this day trip from Siena. Led by an expert guide, travel to the cellars to learn about the production process and meet the locals behind the delicious red wine. Then, pause at a family-run winery for an authentic Tuscan lunch before exploring the village of Montalcino and the abbey of Sant'Antimo. Stop for additional tastings along the way and conclude with transportation back to Siena. Group size is reserved to eight people for a more intimate experience.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$172.77
From
$172.77
Taking safety measures

Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena

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Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.
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  • 4 hours
  • Free Cancellation
From
$125.59
From
$125.59

Chianti Wine Tasting and San Gimignano Day Trip from Siena

Chianti Wine Tasting and San Gimignano Day Trip from Siena

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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
$51.83
From
$51.83
Taking safety measures

Siena Vespa Tour Including Lunch at a Chianti Winery

Siena Vespa Tour Including Lunch at a Chianti Winery

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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
$159.19
From
$159.19

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

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
$185.11
From
$185.11
Taking safety measures

Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

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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 takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$55.53
From
$55.53
Taking safety measures

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

Private Tour: Siena Walking Tour

Private Tour: Siena Walking Tour

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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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$177.50
per group
From
$177.50
per group
Taking safety measures