All Chianti Tours & Excursions in 2026

Ride through the stunning Crete Senesi in Buonconvento with an expert guide, just a short distance from Montalcino and Siena, in a UNESCO World Heritage landscape unlike any other. Suitable for all skill levels, this experience includes a gentle introduction to horseback riding and is guided by local experts who will lead you along scenic trails, past medieval villages, and through rolling hills. What makes it truly unique? The blend of unspoiled nature, centuries-old history, and the authentic charm of Tuscany—experienced from the saddle, at the rhythm of your horse.

Benefit from a private full-day tour of Tuscany with round-trip transportation from your accommodation. Have free time during your visits to Montalcino, Pienza, and Montepulciano, and have the option to stop for lunch, and wine or cheese tastings in the countryside. Travel in comfort in an air-conditioned private vehicle with hotel pickup and drop-off included.

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.

Visit a family-run winery in Chianti to experience the traditional side of local winemaking. With an included tasting of several house wines, this tour of Montefioralle Winery goes from Chianti classic to sweet vin santo. In warm weather, you can sample the wine in a scenic outdoor spot with views of the vines and the surrounding historic village.

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. For children under 12, the class is adapted to be age-appropriate and engaging.

Live an authentic experience in the heart of Chianti, on the family farm in Montefioralle. We will welcome you in a warm and traditional environment to let you discover the wines, oil and Tuscan cuisine. During the experience you will taste rich traditional chopping boards made with locally sourced and strictly homemade (non-industrial) products, special wines, personally produced olive oil and final dessert. After the tasting, for those who wish, it will be possible to take a short walk through the vineyards to discover how the wine is born. We believe in a simple, authentic and genuine welcome. Here you will not find an experience built for tourists, but a real moment of Tuscan life, made of wine, food and conviviality.

Immerse yourself in the Chianti region’s spectacular scenery, discover its historic and picturesque villages, and even visit one of its highlight wineries, all in just half a day: this electric-bike tour makes exploring simple. In the morning, set off with just a small group for company: you’ll see the Castello di Montefioralle, will visit the Abbey of Badia di Passignano, and will enjoy wine tastings and lunch at a local winery.

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.

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.

Experience the food and culture of the Italian countryside by joining this family-style cooking class. By taking a class in a Tuscan farmhouse, you can learn to make traditional recipes that you won't find in typical cooking classes in big cities. Plus, sharing conversations over lunch gives you the chance to get to know local Italians.

Rather than bringing home souvenirs from your trip to Chianti, this experience allows you to bring home new skills—the knowledge of how to make authentic Italian pasta from scratch. Taking place in a beautiful villa in the Italian countryside, the experience is private, which ensures one-to-one guidance from your instructor. Learn to prepare 2–3 types of fresh pasta with sauces—such as gnocchi, ravioli, and tagliatelle—and then enjoy feasting on them after your lesson.

My husband and I want to introduce the products of our company through unique experiences in contact with nature immersed in the Tuscan countryside: the search for truffles is a unique experience that you will appreciate in all its forms, followed by the school of homemade pasta and lunch based on truffles with tasting of our wines and extra virgin olive oil.

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.

Join Francesco, a proud Tuscan host, in the serene garden of our farmhouse nestled in the Chianti hills. Experience a day as part of our family, learning traditional Tuscan recipes, cooking together, and enjoying a feast of homemade pasta and secret desserts. Immerse yourself in our warm hospitality, accompanied by excellent Chianti wine. Perfect for families and groups, you'll even receive a special gift to remember the dish you cooked.

Enjoy an exclusive one-hour wine tasting experience, complemented by warm homemade bread and exquisite Tuscan olive oil. Stroll through the vineyard before indulging in a guided tasting of three exceptional local wines. Discover the traditional methods and techniques used in producing high-quality wines. During the tasting, you’ll savor three outstanding selections, 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 unforgettable moments and feel free to share your experience on social media!

Explore the enchanting Chianti Classico wine region on a thrilling expedition aboard a classic Land Rover Series III. Choose between a morning or late afternoon tour, where you’ll wind through ancient hilltop villages and visit two charming family-run wineries. Indulge in exquisite wine and olive oil tastings, complemented by a light Tuscan lunch or antipasto platter. This intimate experience, with a maximum of six guests, ensures personalized attention and a deeper connection to the local culture and flavors. - Morning tour includes two winery visits and a light lunch of local specialties - Afternoon tour features a guided winery visit and antipasto tasting - Maximum group size of six for a personalized experience - Departures from Hotel Villa Bordoni in Greve in Chianti, with options for public transport arrangements

You will be in the middle of the Chianti classico area, enjoying our beautiful farm, having a typical Tuscan dinner including olive oil tasting over our olive Grove under the sky serves by all our family.

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.

Much more than a cooking course, it will be a unique experience. Sight, smell, hearing ... in this path the 5 senses will be involved, so as to leave you with an unforgettable memory. This experience comes from a childhood memory, spent outdoors. It has the scent of freshly cut grass, the passion for traditional cuisine and the serenity of an atmosphere that warms up under the notes of the Italian Opera.

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.

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.

During a guided tour through the vineyards with a picturesque view of Montalcino, you will learn about biodynamic viticulture. Afterward, a nicely arranged table awaits you, where you will get served 6 wines in 3 flights with matching, specially developed Gourmet Bites.

Discover three of Tuscany’s most beautiful towns as you explore Pienza, Montalcino, and Montepulciano in one day on this walking tour. With a private guide, see the splendid 16th-century Renaissance palaces of Montepulciano and walk through the town of Pienza, built by Pope Pius II. In Montalcino, take a guided tour of a winery and taste the renowned Brunello de Montalcino wine. Note: transportation is not included.