Top Siena Holidays

When you’re in the Tuscan city of Siena, don’t miss the chance to discover its famous wines and enjoy some local food, too. This small-group wine tour visits a winery near Siena’s historical center, and gives the lowdown on the winery’s organic production methods. After visiting the vineyard, you’ll savor a meal made with local produce along with samples of five organic wine varietals. Numbers are limited to 12 per group.

Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.

Learn how to make pasta and tiramisu in a popular Siena restaurant. Enjoy a glass of Prosecco upon arrival, and a glass of wine with your meal.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

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.

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.

Sip Tuscan wine in a medieval castle during a tasting session in Montalcino. Hosted by a professional sommelier, the experience ensures you get the lowdown on the wine as you taste it. Enjoy three varietals including a glass of the prestigious Brunello di Montalcino DOCG, along with local bread or breadsticks and olive oil.

Explore the fascinating world of Tuscan sparkling wines with us! Book our unique experience now and discover what makes our business so special. During the guided tasting, you will be immersed in the art and science of sparkling wine production. Our wine educators will guide you through an exclusive selection of three Tuscan sparkling wines, each produced with a different production method: the classic method, the charmat method and the ancestral method. This experience will not only allow you to savor the unique flavors of these high-quality sparkling wines, but will also give you an in-depth understanding of the different techniques used in their production. You will be fascinated by the diversity of aromas and complexity that each production method adds to the wine.

Off-road mini tour in a vintage Jeep through the landscapes of the vineyards. Taste Poggio ai Laghi premium wines, oils & vinegars. Enjoy the Tuscan Appetizers that enhance the flavors of each wine. Our wine expert will enhance this experience with Art & History.

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.

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.

Explore some of the most popular Tuscan hill towns on this day trip to Siena, San Gimignano, and Monteriggioni from Florence. Enjoy visiting each town independently while also having the round-trip transportation organized in advance. Learn about the famous region from the tour leader on board the bus, listening to informative commentary as you travel.

There are places you visit and others you live. A few minutes from Siena, between the Chianti hills and the Crete Senesi, the experience slowly takes shape on our panoramic terrace, in the shade of an ancient white mulberry tree. What makes it special is the opportunity to taste our wines directly with those who produce them, in a family-run cellar where each bottle is born from the link with the territory. It is not a standard tasting, but an authentic moment made of stories, flavors and genuine hospitality. The wines tell the story of the territory, the typical Tuscan dishes accompany them and the landscape completes the experience. If you are looking for a real meeting with Tuscany, made of details, hospitality and dedicated time, this is the right place.

Between Chianti and Crete Senesi, a few minutes from Siena, San Giorgio a Lapi offers a Premium Wine Tasting dedicated to those who want to discover wines that are unlikely to be found elsewhere. What makes this experience unique is the opportunity to taste wines without added sulphites and interpretations of ancient Tuscan grape varieties such as Colorino, Canaiolo and Sangiovese, told directly by those who grow and produce them. On the panoramic terrace overlooking the Tuscan hills, each wine is accompanied by a selection of typical local flavors designed to enhance its aromas and characteristics. An authentic and relaxed experience, designed for those who want to learn about wine through the territory, people and stories that make it unique.

This experience offers a dynamic tasting path in the heart of Siena, designed for those who want to discover wine in an engaging way, without leaving the historic center. An ideal format to combine culture, conviviality and wine pleasure in a short time. The tasting combines two different styles: bubbles and red wines, allowing participants to understand the main differences between production methods and expressions of the Tuscan territory, with clear and accessible explanations. The experience is guided by an Expert who accompanies the participants in reading the wine, helping them to recognize aromas, structure and characteristics, making the tasting suitable for both beginners and enthusiasts. The small size of the group guarantees a relaxed and interactive atmosphere, ideal for asking questions, discussing and experiencing an authentic moment linked to the local wine tradition.

Take your Tuscan wine tasting to the next level with this one-of-a-kind experience set in an authentic medieval aqueduct hidden below the historic city center. Settle in among brick vaults and tunnels dug directly into the stone to sip a selection of Brunello di Montalcino and Super Tuscan wines from the vineyards of Siena and Chianti, paired with local cheese.

There's no better way of immersing yourself in local culture than a cooking class. Get an authentic taste of northern Italy with this small-group cooking class in Siena. Led by a local chef, learn how to craft a delicious spread of Tuscan favorites plus a classic tiramisu. Afterward, enjoy the fruits of your labor as you savor your creations with your group and a glass of vino.

Siena sits in the heart of Tuscany, known across the globe for its excellent regional cuisine. Delve into its traditional specialties with this foodie experience that combines a lesson covering Tuscan wines and gourmet delicacies plus a foodie stroll through the old town to sample them for yourself. Taste a variety of wines paired with cheeses and charcuterie, extra-virgin olive oil, bread, jams, and honey.

Enjoy a wine and food tasting in Siena's stunning Piazza del Campo. Sip on local wines and savor a platter of regional cured meats and cheeses in a relaxed and welcoming atmosphere.

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, a family winery surrounded by the rolling hills of Montalcino. Guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the traditions, craftsmanship and passion behind Brunello di Montalcino production. The experience continues with a carefully curated tasting of premium Tuscan wines paired with a traditional Tuscan lunch featuring local specialities and fresh handmade pasta, creating a journey that combines wine, food and landscape in a truly authentic way. Far from crowded commercial tours, this immersive experience offers a refined and memorable taste of Tuscany in a relaxed and elegant setting. Each tasting is led by expert sommeliers, transforming every glass into a deeper journey through the world of Brunello di Montalcino.

This experience is led by Paolo Nenci, one of Italy’s first “digital farmers”, followed by thousands of people online for his innovative approach to wine and agriculture. The winery was awarded in Dubai in November 2024 for excellence in extra virgin olive oil, a recognition of quality and craftsmanship. You will also taste wines produced with traditional methods, including the historic Vin Santo made with a fermentation mother dating back to 1820. An authentic, award-winning experience in the Tuscan countryside near Montepulciano, far from mass tourism.

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.