Top Chianti Sightseeing Tours

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.

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.

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.

Benefit from a private full-day tour of Tuscany with round-trip transportation from Siena. 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.

Explore the Tuscan countryside while in port in Livorno with a 9-hour private wine tour. Led by an expert guide, take a scenic drive into the heart of the Chianti wine region to learn about the winemaking process and sample local blends. Taste top-quality, Tuscan olive oil and admire the rolling landscape before heading back to your cruise ship.

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.

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raised in Tuscany. -During the 8hr tour you will explore the Gothic city of Siena with its famous shell-shaped Piazza del Campo and the gorgeous cathedral, followed step by step by a licensed TOUR GUIDE! If you love to visit the cathedral there will be to pay at the guide directly euro 5 per person or euro 7pp with priority -In the afternoon you will have the opportunity to visit some of the most famous vineyards, or unknown small family businesses, see their cellars and taste their excellent wines and food. -Then explore the wonderful medieval city of San Gimignano.

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.

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.

Hop on your eBike and embark on a 3-hour journey through Chianti, Italy's Tuscany region. Experience the panoramic views of the countryside and cap off the tour with a delectable aperitif amid a stunning backdrop. Indulge in fine local wines and treat your taste buds to a rich platter of cold cuts and cheeses. Whether you're a novice or an expert cyclist, you're covered with customizable tours based on your age, skills, and group size.

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.

Montalcino, the city center of the territory and important for one of the most famous wines of Italy: Brunello di Montalcino

Welcome to our private and exclusive tour to discover Tuscany aboard a Fiat 500, the iconic Italian car! You will explore hidden medieval villages, where time seems to have stopped, and we will leave you free time to stroll through the cobbled streets and discover authentic local traditions. The tour begins with the reservation of your vintage Fiat 500, an iconic Italian car, which will make you feel like protagonists of a period film as you travel through the evocative Tuscan landscapes. You will make a stop in a historic cellar, where you can taste some of the best Tuscan wines produced in the region. After the tasting, you will continue to San Gimignano, a charming medieval village famous for its well-preserved medieval towers. You can walk through the cobbled streets and admire the historic architecture of this unique place in the world.

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.