Top Chianti Holidays

For true wine-lovers, there’s no greater thrill than seeing where Tuscany’s specialty red is made. During this in-depth tour of an organic, family-run winery, you’ll learn the ins and outs of Chianti Classico. Tour the scenic vineyard and sample four different red wine varieties inside the atmospheric on-site cellar. Pair your tasting with fresh cheeses and salami, all made from fresh regional products.

Taste your way through Tuscany at a classic wine tasting. After a cinematic journey through a cypress avenue, a trained team will serve you 6 wines in 3 flights at your table. After an introduction to each wine, you will have the opportunity to taste the wines in detail by yourself.

Tour the cellars of Monterinaldi Castle with a sommelier as your guide. This historic castle in the heart of Chianti is the perfect setting to learn all about the winemaking process. After your private tour of the cellars, enjoy a 3-course Tuscan lunch with wine pairings in an 18th century villa.

Enjoy Tuscany to the fullest on a private vineyard picnic. Discover our winery on a guided tour (optional), taste wine in a cozy atmosphere overlooking Montalcino, and enjoy your picnic basket filled with delicious homemade Tuscan specialties.

Enjoy an exclusive one-hour wine tasting experience featuring warm homemade bread and exquisite Tuscan olive oil. Take a leisurely stroll through the vineyard before indulging in a guided tasting of three local wines, beautifully paired with a platter of Tuscan cured meats and cheeses. Discover the traditional methods and techniques used to produce high-quality wines. During the tasting, you’ll savor three exceptional wines, including the world-renowned Brunello and Rosso di Montalcino. Plus, you’ll have the unique opportunity to taste wine straight from the wooden barrel! Capture your memorable moments and feel free to share your experience on social media!

Learn how to create up to three classic Italian dishes—including homemade pasta—during this private cooking workshop in Chianti. Head to a scenic countryside home for an intimate lesson led by a pair of local cooks. Workshops include a wine and olive oil tasting and home-cooked meal with vegetarian and vegan options available.

Make the most of your time while in port in Livorno and avoid wasting hours trying to explore Tuscany by public transportation or rental car on this full-day private wine tour in the Chianti hills. Led by a wine-focused guide, take a scenic drive into the heart of the Chianti wine region and visit a local winery to learn about the winemaking process and sample local blends. Taste top-quality wine and Tuscan olive oil while admiring the rolling landscape before heading back to your cruise ship.

Discover Chianti Classico with a visit and tasting in Viticcio: explore the winery, discover the winemaking and taste our best wines. An authentic Chianti experience! Our experience takes place in a historic winery in the heart of Chianti Classico, where the Tuscan wine tradition is breathed in every detail. The location offers a breathtaking panoramic view of the surrounding hills, making each tasting an unforgettable moment immersed in the beauty of the landscape.

Discover Tuscany and biodynamic viticulture on a winery tour with a breathtaking view of Montalcino while you learn about our philosophy. During a seated wine tasting, we will serve you 6 different wines and give you a short introduction to each of them. Then you will have the possibility to taste them independently.

What makes this experience truly unique is the opportunity to discover the authentic soul of Montalcino through the intimate atmosphere of Paradiso di Cacuci, a family winery nestled in a small “corner of Paradise” among the rolling Tuscan hills. Far from crowded commercial tastings, guests are welcomed into a place where tradition, landscape and passion create a genuine Brunello experience. From walking through the vineyards to exploring the ageing cellar, every moment offers a deeper connection to the world of Brunello di Montalcino and the craftsmanship behind each bottle. The experience is enriched by breathtaking views, expert sommeliers, carefully selected wines and traditional Tuscan flavours, creating a refined journey into the heart of Tuscany. Whether you are a wine enthusiast or simply searching for an unforgettable moment in the Tuscan countryside, Paradiso di Cacuci offers a timeless experience shaped by authenticity, elegance and the unique charm of Montalcino.

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through our organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce our high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative.

Guests will be immersed in the countryside of the southern area of Montalcino and will enter the atmosphere of Molino di Sant'Antimo and the tradition of the Vittori family. This experience, which includes a visit to the cellar and a 4-course lunch, will lead our guests to discover the typical dishes of Tuscan cuisine proposed by the Vittori family in the Montalcino company. During the experience the wines of our production will be tasted such as: Gina Rosato or Il Bianco Chardonnay Igt Red of Montalcino Doc Brunello di Montalcino DOCG This selection is designed as an introduction to our winemaking history. Rosso and Brunello are central wines in Molino. Gina is the idea outside the box, an Italian Rosé with a French soul.

What makes this experience truly unique is the opportunity to enjoy an authentic Tuscan dinner among the vineyards of Paradiso di Cacuci, surrounded by the peaceful atmosphere and timeless beauty of the Montalcino countryside. As the sun sets over the rolling hills, guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the passion and traditions behind Brunello di Montalcino. The evening continues with a curated tasting of exceptional Tuscan wines paired with traditional cuisine, creating a journey where every glass and every dish reflects the soul of Tuscany. From Brunello Riserva selections to handmade pasta and authentic Tuscan flavours, the experience combines elegance, intimacy and a true sense of place. Far from crowded restaurants and commercial tastings, this is a refined and immersive evening designed for those seeking exceptional wines, authentic food and the unforgettable atmosphere of a dinner in the vineyards under the Tuscan sky.

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine of the Chianti lands, immersed in the green countryside, this is the tour for you. The small group size of no more than 6 pax will make you appreciate the tranquility and peace of Chianti

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative. Tasport From Montalcino

Your experience will start directly at your hotel, where you will climb aboard an air-conditioned vehicle with a professional driver. You will visit a historic wine cellar to discover the aromas of the barrel room and the quiet of the cellars. Enjoy different vintages of local Chianti Classico wines. After, you will be welcomed to a family-run winery to visit the cellar, have a wine tasting, and enjoy a full lunch accompanied by locally produced wines for those who wish to discover the pleasure of local cuisine. In the end of the tour, you will visit a third winery, a biological one. You will visit the cellars and enjoy a guided tasting of three local wines with tastings of olive oil with bread and Cinta Senese Dop cured meats. Please note that the order of visits and the wineries could change due to availability. When select SELF DRIVE OPTION, you have to travel with your OWN car. NO TRANSFER is included. It is NOT possible to take the tour using public transportation.

Enjoy an unforgettable day: let yourself be guided through the rolling hills and vineyards while admiring the beautiful Tuscan landscapes! Our tour will combine the perfect Brunello di Montalcino wine with our typical Tuscan cooking.  Thanks to this tour you will be able to appreciate wines and food and to learn more about our history and traditions: in two words, our Tuscan life style!

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.

Walking, discovering, and tasting: In the heart of Tuscany, through the lands of the Chianti region, we accompany you on daily excursions combined with original experiences to search for artistic, wine, gastronomic, and artisanal treasures. We walk to come into contact with this region’s nature: the hills, the streams, the woods, the trails through vineyards, and the wildest corners. We discover hidden gems: old farmhouses, parish churches, castles, and workshops where craftsmen create as they did once upon a time. We taste the fruits of this land: Chianti wines together with traditional dishes, but we also take in the scents of the flowers, the colors of the fields, and the sounds of every setting that we pass through. Each hike reveals an aspect of this land and combines outdoor activities with unique experiences to be enjoyed together, sharing every step, every taste, and every emotion.

Step into the heart of Tuscan cuisine and enjoy a fun, hands-on cooking experience in Chianti, where food, wine, and good company come together. Led by a professional chef, this interactive class will guide you through the preparation of two of Italy’s most beloved dishes: pizza and tiramisu. This experience is designed to be relaxed, social, and engaging—perfect for travelers of all skill levels. Whether you’re a beginner or a food lover, you’ll enjoy learning in a welcoming atmosphere while sharing laughs and stories with fellow participants. Once the cooking is done, sit down and enjoy the meal you’ve prepared, accompanied by local wine. It’s the perfect moment to relax, connect, and savor the authentic flavors of Tuscany. More than just a cooking class, this is a true Italian experience—where you cook, eat, drink, and create lasting memories.

Immerse yourself in the authentic culture of Chianti with a wine tasting in Radda, a medieval village nestled in the Tuscan hills. Surrounded by Sangiovese vineyards, this experience offers more than just a tasting—it’s a journey into local tradition. Guided by an expert, you’ll explore the full winemaking process, from fermentation to barrel aging, before sampling three typical Tuscan wines and a Vermouth. A perfect way to connect with the land, its history, and its flavors.

We are Federico, Raimondo, and Riccardo, and we’re excited to welcome you on this unforgettable tour! Discover the beauty of our land through its flavors—taste our organic wines, including red Chianti Classico Mariagioconda, rosé Lo Stinto, white Il Pinone, and orange Il Matan, along with our finest extra virgin olive oil and the seasonal vegetable garden we grow. As we explore the breathtaking Chianti landscape, you’ll visit our vineyards and cellar, where we’ll share the secrets of aging and caring for our wines, nurturing both the bottles and the fields. Together, we’ll taste four organic wines and our exceptional olive oil, paired with delicious local cheeses and cold cuts. The tasting will take you on a journey from crisp white native wines to the deep flavors of Sangiovese red. Get ready to immerse yourself in nature and experience its most precious gifts firsthand!

You will start exploring Montalcino with a guided tasting of the famous Brunello di Montalcino. You will be welcomed in a historic wine bar in the very heart of Montalcino's old center to explore one of the most famous wines in the world! Here you will have a free glass of Brunello di Montalcino wine. Additionally, you will have a wine card with a value of €5 per person, so you could extend your tasting experience even further! After, you will proceed with a guided visit to a historic cellar located inside the ancient walls of Montalcino. A unique experience to dive into history and winemaking by learning something new from a family that produces wine for more than 20 generations. Finally, enjoy Montalcino wines with a breathtaking view over the Val d’Orcia. BONUS: Together with the tasting vouchers you will get a detailed 1-day digital itinerary, full of maps, and tips on what to see, taste and buy, so you could enjoy your stress-free holiday experience and fully enjoy Montalcino.