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.

Welcome to a unique experience in the heart of beautiful Tuscany! Our Chianti tour invites you to discover the essence of this legendary wine region, all with the luxury and comfort of our exclusive chauffeur service included. From the moment we pick you up at your accommodation, you will immerse yourself in a dream journey through the most impressive landscapes in Italy. Our expert drivers, knowledgeable about the area, will guide you through the winding roads between hills, dotted with vineyards, olive groves and cypress trees, giving you panoramic views that will leave you breathless. During the tour, you will have the opportunity to see family-owned vineyards, where you will be greeted with warm Tuscan hospitality and have the opportunity to taste some of the most exquisite wines in the region. From the iconic Chianti Classico to other local varietals, each sip will transport you to centuries of wine tradition.

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.

Experience the authentic side of Tuscan cuisine with this exclusive farmhouse cooking class. Meet your local host at their farm in the Chianti hills and enjoy a hands-on lesson to learn how to turn out fresh ravioli or “pici” pasta, beef ragu or other sauces, pizza dough, and chocolate “salami”. Relax over a homecooked meal after your lesson to enjoy the dishes you've prepared paired with local wine.

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.

Delve into the fascinating world of olive oil with a guided tour at Frantoio di Montalcino, one of Tuscany’s most celebrated olive oil mills. Get your taste buds ready as you learn about traditional pressing methods, as well as modern ones, and the origins of olive oil in a countryside setting. After your tour, sit down for a delicious tasting session to sample the finest extra virgin olive oils served alongside warm Tuscan bread and local specialties.

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.

Sip some of Italy's most famous wine during a visit to an organic winery in the heart of the Chianti region. Tour the vineyards and organic winery between Radda and Panzano, right in the Chianti Classico wine-producing area. Learn about local wine making, and take part in a wine-tasting session at the conclusion of your tour. Sample between 3 and 6 wines, accompanied by appetizers that include bread with olive oil produced on-site.

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.

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.

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.

Take part in a safe and comfortable hot air balloon flight over Tuscany’s most iconic landscapes. Choose from flights over Chianti, Siena, or San Gimignano. The Chianti flight offers stunning views of rolling hills, vineyards, olive groves, forests, and historic villages. Admire medieval castles, Renaissance villas, and towns such as Siena, San Gimignano, Colle Val d’Elsa, and Poggibonsi from above. Opt for the San Gimignano flight to marvel at its famous medieval towers, the Vernaccia vineyards, and even the distant marble peaks of Carrara. Those who choose the Siena flight will enjoy breathtaking views of the Cathedral, Piazza del Campo, and the surrounding countryside. After landing, before heading back to the meeting point, savor a light breakfast featuring local products — the perfect way to end this unforgettable Tuscan adventure. The time selected during the booking process is indicative and may be subject to change. You will be contacted by the facility if necessary.

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.

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.

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.

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.

We are excited to invite you on the iconic Vespa, a means of transportation that combines comfort and style. Imagine yourself driving through the vineyards and undulating hills of Chianti, enjoying the breathtaking view in which you can glimpse San Gimignano and the entire province of Florence and Siena. Be enchanted by nature painted in the colors of the sunset. And to end the experience on a high note, you will be treated to an excellent dinner, made from fresh, local product in SiChef's wonderful villa.

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.

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.

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.

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.

The Fresh Pasta and Italian Ice Cream Course at our SiChef cooking school, located in the picturesque Chianti region, offers an authentic and exclusive culinary experience. This course, open to cooking enthusiasts of all levels, is a journey into the art of fresh pasta and Italian ice cream, two pillars of Italy's culinary tradition. During the course there will be both theory and practice and the preparations taught will be easily replicable at home. At the end of the course a diploma will be awarded and the recipes will be sent to the participants.

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!