Top Siena Half-day Tours

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Avoid the hassle of organizing transport and winery visits in Tuscany on your own. This small-group experience simplifies a day in Chianti, combining scenic travel with curated tastings at local wineries and time to explore Monteriggioni’s medieval charm. Enjoy a relaxed, well-paced outing that lets you focus on the region’s flavors and landscapes rather than the logistics.

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace: Piazza del Campo, the Duomo, Basilica di San Domenico and much more! You'll get to know the stories and curiosities of Siena! But also you will discover everything about local foods, Italian aperitivo in authentic local restaurants, and much more! What are you waiting for?

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at Palazzo Pubblico, an architectural marvel serving as the seat of governance. Meander through historic streets, passing Palazzo Tolomei and Palazzo Salimbeni, both UNESCO-listed treasures. Continue to the Basilica of San Domenico, housing the relics of Saint Catherine, before a visit to the Sanctuary of St. Catherine of Siena. Admire the Baptistery and opt for a guided tour of the awe-inspiring Siena Cathedral, adorned with masterpieces of Italian artistry.

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 as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier.

Siena has one of the most intact medieval cityscapes in Italy and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, town hall, and Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

Discover the medieval landmarks of Siena and learn about their significance on this private walking tour. During this half-day tour, walk with your guide to highlight attractions around Siena’s historical center, including the Piazza del Campo, Siena Cathedral, and the Basilica di San Domenico. There is a limit of eight travelers on the tour and admission fees to attractions are not included.

Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

Discover the most authentic side of Tuscany through a journey that weaves together landscape, history, and taste. The experience begins among the vineyards, in the heart of Chianti, leading to the small church of San Giorgio a Lapi, dating back to the 12th century, home to three remarkable frescoes by Nasini — a quiet place, suspended in time. The visit then continues in the cellar, where our work takes shape: from vinification to aging, each step reflects a choice, an idea, a story. The experience then opens onto the panoramic terrace overlooking the Crete Senesi, under the shade of an ancient white mulberry tree, with a guided tasting of our wines accompanied by a full Tuscan meal: starter, first course, main course with side dish, and dessert. A moment to be lived slowly, among scents, light, and silence.

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, get familiar with your bike and helmet, and head into the Chianti Hills. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local farm/winery, where you can enjoy a traditional meal and generous wine tasting.

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views 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) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

Skip the dry guidebook and hassle of following a map and discover the medieval streets of Siena with a personal guide at your side who knows how to bring its history to life. Take in the top sights plus find hidden-away corners far from the tourist crowds, learn history and lore that most tourists miss, and create a personalized itinerary that suits your pace and interests.

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.

Siena, a medieval city rich in history and spirituality, is one of the most fascinating destinations for those who wish to have a unique religious and cultural experience. On this tour, accompanied by an experienced Catholic guide, you will discover the heart of the Sienese faith through a visit to Siena Cathedral, one of the most beautiful churches in Italy, and the House of St. Catherine, the place that holds the memories of the city's patron saint.

Join us for a hands-on cooking class and wine-tasting experience on a beautiful Chianti farm. Over 4 hours, you’ll experience Tuscan culinary traditions, starting with a guided lesson from a professional chef. Using fresh, local ingredients, you’ll prepare classic Italian dishes, from homemade pasta to savory sauces. After the cooking session, relax and enjoy a guided wine tasting featuring IGT, Chianti, and Chianti Classico wines. Pair your wines with delicious snacks like bruschetta and salami while learning about the rich winemaking traditions of the Chianti region. Finally, sit down to savor the meal you’ve prepared, complemented by fine Tuscan wines. Tips: Dress comfortably for the kitchen, and arrive 15 minutes early to get settled. Everything you need, including ingredients, dinner, and drinks, is included, so come ready to enjoy a true taste of Tuscany!

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

Spend your day through the picturesque Tuscan landscape on an original Vespa scooter, enjoying peaceful roads that wind through the rolling hills of Chianti. This unique experience allows you to immerse yourself fully in the sights, scents, and sounds of the Tuscan countryside. As you navigate the winding roads, take in panoramic views of vineyards, olive groves, and ancient farmhouses dotting the landscape. Midway through your excursion, make a stop at a renowned winery nestled in the heart of the Chianti region. Here, indulge in a delightful wine tasting experience, savoring the flavors of locally produced wines that have been crafted with passion and expertise. After replenishing your energy, discover hidden gems off the beaten path, uncovering the rich history and culture that define this beloved region.

Explore Chianti’s backroads and beautiful vistas while traveling in a private 4WD on this tour with hotel pickup. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste several Chianti Classico wines along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a traditional Tuscan lunch at a scenic family estate.

Taste your way through the most delicious private food tour of Siena as you immerse yourself in Tuscan culinary culture with a knowledgeable local host. Indulge in six or 10 iconic treats, including pastries, espresso, and savory bites, while exploring favorite local spots and must-see landmarks like Piazza del Campo and Torre del Mangia. Along the way, discover the rich flavors and history that make Siena unforgettable.

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.

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills. Explore a local vineyard with your private guide and discover the winemaking 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.

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

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 a few 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.