All Chianti Tours & Excursions in 2026

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.

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.

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.

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.

Enjoy a private picnic in the vineyards with Tuscan specialties,Taste the famous wines of Montalcino,Admire the spectacular views of the Montalcino valleys

WHAT TO EXPECT Picnic basket with typical products Inside, in fact, you will find not only a comfortable blanket and compostable and recyclable tableware, but also a selection of typical Tuscan products such as bruschetta and a selection of 0 kilometer cured meats and cheeses. Experience in contact with nature After walking through the vineyards and breathing in the scent of the vines, you can choose the place that best belongs to you, where you can enjoy your bottle of wine and your picnic comfortably sitting on your blanket. Bottle of wine of your choice When booking this fabulous picnic, you can choose between a bottle of Rosso di Montalcino or a bottle of Brunello di Montalcino. This choice is fundamental: it will in fact be what will accompany lunch in front of the wonderful spectacle that nature gives you. Both wines are produced by the farm you are on. In fact, you can taste your wine while sitting among the vines that yield the fruits for divine nectar.

We are located in the Chianti Classico area halfway between Florence and Siena, we are a farm that produces extra virgin olive oil and saffron. The passion for olive trees and oil has led us to want to make this wonderful reality known to all those who are interested in this product of our lands

Chianti is known for its excellent cuisine, so there is no better place to pick up pro tips and techniques in the kitchen. With this pizza and tiramisu class, learn how to prepare two of Italy’s most famous dishes in a single lesson. Go hands-on under the watchful eye of your instructor to top your pizza and assemble your tiramisu, then taste the fruit of your labors over lunch or dinner.

Avoid stress and enjoy a comfortable private transfer to Sorrento from Florence. The driver will pick you up from the airport, hotel, apartment, or train station and drive you to your destination in Sorrento. Ride in a clean car and relax all the way while the English-speaking professional driver takes the wheel. Your safety is of utmost importance and you can rest assured knowing you'll arrive at your destination on time hassle-free.

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.

Enjoy a hands-on experience as you harvest olives with a traditional Italian family at their olive grove. Help hand-pick olives and collect them in large nets before transporting them to the nearby mill to be processed. Once the harvest is finished, enjoy the fruits of your labor with fresh olive oil to accompany your lunch as you learn about the traditions and customs of the Tuscany region.

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.

Break up your sightseeing and connect with a passionate home cook in the hills of Chianti far from the tourist crowds with this private cooking class. Join your local host in her Tuscan kitchen to discover the secrets to preparing pizza and tiramisù from scratch like a pro with personalized, hands-on instruction. Then, sample your handiwork over a celebratory final tasting paired with area wines.

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.

Join us in our little corner of paradise and, through a fun and interactive cooking class, you will learn how to prepare delicious recipes typical of Tuscan cuisine with a professional chef, while tasting the excellent local wine. A hands-on experience designed for food lovers, allowing you to explore Tuscan cuisine in more depth than you would simply by eating in restaurants. You will discover, step by step, how to prepare a perfect Tuscan lunch, from appetizers to desserts, including the art of making fresh pasta. You will learn how to cook different types of pasta such as ravioli, tagliatelle, and gnocchi. The recipes will be provided to you after the lesson, making sure you can recreate Tuscan dishes in your home as well. What we offer you is a unique experience, in a magical location, where you will learn the essence of Italian gastronomic culture. We look forward to meeting you and sharing our passion for Italian food with you!

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.

Trace the historic Via Francigena pilgrim route by e-bike, taking in some of the most charming hilltowns in Tuscany along the way. Begin your adventure with a walking tour of Siena before heading out with your guide to pedal through the Tuscan countryside. Stop to admire the medieval villages of Monteriggioni and San Gimignano before heading back to Siena.

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.

Visit three top Brunello producers in the UNESCO-listed Val d'Orcia in a single day with this exclusive wine tour. Enjoy the ease of hotel pickup and all-day transport so you can imbibe worry-free, and tour three luxury wineries with tastings of Brunello, Super Tuscans, and other high-end reds at each. Take in views over the rolling vineyards during a wine-pairing lunch and connect with the winemakers during your private visits and tastings.

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!

Stepping into this enchanting village is a truly unique experience in itself, with views over the hills, a magical garden, olive trees, birds chirping, and endless picture-perfect views. You'll experience a painting workshop which is a lot more than an art class: it is an art party open to all levels and ages, where you'll rediscover the fun of painting and playing with color in a friendly, magical environment. I am an artist and filmmaker now based in the village of Montisi, but for the past 17 years I have lived in Los Angeles where I have incorporated the skills and enthusiasm of the Californians into my Italian upbringing making me a bridge between Italian and American cultures. Living in this incredible place is a dream come true for me, and in my workshop I share this dream with you. Open to all levels!

Cooking Experience & Lunch: Blend Tuscan and Apulian flavors in an historic villa for a unique taste!

Discover the wines of Montalcino on a 3-hour wine tour that visits two wineries in the region. Enjoy wine tastings and tours of the vineyards, gaining insight into the history of the famous Rosso and Brunello di Montalcino wines. Travel with a small group and enjoy viewing the picturesque countryside along the way.

You can't visit Italy without trying at least one pasta dish... So, we'll teach you two! Learn how to roll 'sfoglia' (fresh pasta) by hand and how to prepare 2 simple different kinds of pasta from scratch with your Cesarina. As the icing on the cake you will learn to prepare also the iconic Tiramisu. Share your passion for the Italian cuisine as you make new friends in this hands-on cooking class. It's a great way to truly experience Italian culture. • Learn to roll 'sfoglia' (fresh pasta) by hand • Learn to make 2 iconic pasta types • Learn to make the iconic tiramisu • Small-group cooking class with a maximum of 12 people. Share your passion for the Italian cuisine with other lovely guests • Enjoy an Italian Aperitivo to warm-up Cesarine is Italy’s oldest network of home cooks all over the country. They are welcoming hosts that open the doors of their own homes to curious travellers for immersive culinary experiences.