Top Siena Holidays

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.

There are many ways to spend an evening in Tuscany, but few allow you to experience it from the inside. Just a few minutes from Siena, between Chianti and the Crete Senesi, this experience takes you through vineyards, cellars, and history, guided directly by the people who produce the wine every day. What makes it special is the combination of a visit to a family-run winery, a tasting of our wines, and a traditional Tuscan dinner served at sunset on a panoramic terrace overlooking two of the most fascinating landscapes in the Siena area. It is not just a wine tasting or a dinner, but an authentic experience where wine, territory, tradition, and hospitality come together in a relaxed and genuine atmosphere.

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.

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.

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.

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 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.

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.

The hills south of Siena are home to some of Tuscany’s most prestigious wines, but navigating the country roads can be a challenge. This private tour includes visits to three historic wineries in Montepulciano and Montalcino for tours, tastings, and lunch. Break up your cellar visits with a stop in Pienza for a pecorino cheese 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.

Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Exploring in a group no larger than 15, discover 600 years of history, including the chapel, the vineyards, and the cellars. Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.

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.

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.

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.

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.

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that includes Truffle, Chili Pepper, and Extra Virgin Olive oil. Aceto Balsamico tasting that includes Onion and Modena vinegars. Tuscan appetizers: Salame toscano, finocchiona, prosciutto crudo toscano, pecorino, bruschetta with fresh tomato and basil, cialda di pane tostato with Extra Virgin Olive Oil. First course: Penne al ragù or Penne al pomodoro. Second course: Arista with roasted potatoes. Dessert: Cantuccini and Vinsanto

Discover the magic of Tuscan winemaking on this sensory-rich Golf Cart mini tour through the scenic Poggio ai Laghi vineyards. Hop into a golf cart and journey through our vineyards, where tradition meets nature. It’s an experience that engages all your senses, leaving you with a deeper appreciation for the art of winemaking and the beauty of the Tuscan countryside. Your wine expert will walk you through the tasting journey during your lunch. As you learn about the winemaking process and the passion behind each bottle, the food and wine experience becomes more than a meal—it becomes a memory, and quite possibly your most cherished souvenir from the Tuscan countryside. You’ll sample a selection of our finest wines, showing the skill and dedication of your winemakers. You’ll also savor the winery’s cuisine and exquisite oils and vinegars, each one crafted with the same attention to detail and quality as the wines.

A Round trip TOUR that will start from the ancient city of palio Siena to The hilltop medieval towns of MONTEPULCIANO, PIENZA AND MONTALCINO.

What makes this experience truly unique is the intimate atmosphere of Paradiso di Cacuci, a family winery nestled among the rolling hills of Montalcino, far from crowded commercial wine tours. Guests are welcomed into an authentic Tuscan estate where tradition, landscape and passion come together to create a genuine Brunello experience. From walking through the vineyards to exploring the ageing cellar, every moment offers a deeper connection to the craftsmanship and philosophy behind Brunello di Montalcino. The guided tasting allows travelers to discover the elegance and evolution of Sangiovese through carefully selected wines, perfectly paired with traditional Tuscan flavours. Surrounded by breathtaking vineyard views and the peaceful atmosphere of the Tuscan countryside, this experience is designed for those seeking not only a wine tasting, but a refined and memorable journey into the heart of Tuscany.

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del Moro, or our oenologists, you will explore the Poggio del Moro estate - from the vineyards, to the oil mill, to the cellar and the barrique cellar - and you will learn the production process of our natural wines, free from pesticides and unnecessary production interventions. Poggio del Moro is an out of the ordinary boutique winery, an extraordinary open-air art gallery. Here you will find contemporary art exhibitions or artistic performances, which you can observe while visiting the cellar or tasting your wine in relaxation, an absolutely original and refined experience in an intimate and exclusive environment!

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.

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.

You'll visit the winery’s production area and cellar, gaining an inside look at the winemaking process—from vine to bottle. The experience culminates with a guided tasting of the estate’s wines, right in the Poggio ai Laghi vineyard itself or at a nearby tasting spot, paired with a delicious lunch. Whether you're a wine lover or a curious traveler, this tour offers a rich and memorable experience rooted in tradition and flavor.