Top Chianti Tours, Sightseeing & Cruises

Spend a full day touring the Italian cities of Siena, San Gimignano, and the surrounding area of Chianti. Specifically designed for guests staying in Florence, get picked up directly from the hotel in a comfortable vehicle and take a private tour of these Tuscan hotspots. Learn about the area’s Gothic and medieval history, and enjoy the local vineyards.

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.

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!

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.

Discover the charm of Montalcino and the Val d'Orcia on a full day e-bike tour with a local Guide who knows the territory like the back of his hand. Ride among the most beautiful dirt roads in the world in a Unesco heritage area. You will ride about 45 - 50 km through the low-traffic roads of the Tuscan hills, while a certified Guide will share with you the history and secrets of the territory. You will stop at a historic winery to taste the renowned Brunello di Montalcino and the oil produced by the company, accompanied by a delicious platter of local cold cuts and cheeses. You will admire the Romanesque Abbey of Sant'Antimo before returning to Montalcino, making your trip an unforgettable experience. - E-bike tour of about 5 hours with departure and return to Montalcino - Certified Guide available for assistance and information - Tasting of 3 Brunello wines with cold cuts and cheeses - Panoramic routes between dirt and paved roads of the Val d'Orcia

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.

Ride through the rolling hills of Montalcino on a private e-bike experience for travelers seeking authenticity, exceptional wines, and a deeper connection with Tuscany.Set in the UNESCO-listed Val d’Orcia, the journey unfolds at a relaxed, immersive pace. Premium e-bikes ensure effortless riding, and scenic routes along the Via Francigena offer photo spots, storytelling, and local legends far from crowds. Discover hidden corners and panoramic vineyards on a private, immersive tour for lasting memories.Led by a certified guide, you explore the history, culture, and atmosphere of this region beyond a standard tour.The experience culminates with an exclusive winery visit, followed by a refined Tuscan lunch and curated wine pairing. Savor Brunello and Rosso di Montalcino, both organic certified, in a private, intimate setting. Designed for couples, families, and discerning travelers, this is an elevated, immersive way to discover Montalcino — private, seamless, far from ordinary tours.

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.

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.

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.

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.

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

Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.

If you are looking for an experience that goes beyond just tourism, here is why you should book your day at La Collina del Sole : A unique sensory awakening Forget the daily grind. You will be greeted by the peace of the Tuscan countryside with a warm herbal tea, starting a path that stimulates the senses. Discovering the secret of quality You will not only see flowers, but you will learn the art of biodynamic cultivation. You will understand why saffron is the most precious spice in the world and how ancient history is intertwined with respect for the land. An explosion of authentic flavours The culmination of the experience is an excellent Tuscan brunch. It's not the usual meal: you'll taste the saffron risotto, the intensity of the freshly pressed New Oil on crispy bruschetta and the elegance of Chianti wine. It is a tribute to the local culinary tradition. Beauty that regenerates You will find yourself immersed in a postcard landscape, where time seems to stand still.

Experience Montalcino, the Kind of Sangiovese, or Chianti Classico with its black rooster, or Bolgheri and its unique supertuscan blends, focusing only on small hidden gems wineries that you can discover with me. Tours are private and for small groups only.

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

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.

We are excited to invite you on the iconic Vespa, a means of transportation that combines comfort and style. During the tour, you will admire the Tuscan landscapes and its hills full of vineyards and olive groves, enjoy the most picturesque places, catch a glimpse of San Gimignano and the whole province of Florence and Siena. But it doesn't end there! At the end of the tour, an unforgettable food and wine experience awaits you: a tasting of typical Chianti wines. You will taste the fine wines produced in the area and learn about their characteristics, thanks to the guidance of expert sommeliers. Program Duration: 4 hours - Meeting at our Villa in Spoiano - Vespa tour with route marked on map - Meeting at the Typical Tuscan Winery near our Villa - Return to the Villa and delivery of the vespas FREE CANCELLATION: it will be possible to cancel within 48h from the beginning of the experience

Excursion in the heart of Chianti, among the rolling hills covered with vineyards, olive groves and dotted with villages suspended in time, we will also visit the ancient Castle of Montefioralle, a museum dedicated to the history of wine and we will be able to taste the most representative wines of the region, in a dream cellar ...

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.

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.

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!