Top Chianti Tours, Sightseeing & Cruises

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.

The experience begins at 10 : 00 in the morning. We will meet at our farm, where we will have a brief introduction to our small family business. Guests will be accompanied by an environmental Guide who will explain the route and provide information on the history, characteristics and peculiarities of the territory, as well as the different animal and plant species we will encounter along the way (if the season allows, we will collect edible wild plants for lunch). We will find a corner in the woods, perfect for a picnic, where we will taste a glass of wine from our company with cheeses and cold cuts. We will resume the journey back to our farm, where a three-course lunch of seasonal agricultural products will be served, including a tasting of our wines and extra virgin olive oil. The planned route is of medium-low difficulty with duration 2 - 2.5 hours.

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.

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.

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.

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.

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!

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.

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.

Escape Florence for the rolling hills of Chianti on this private wine tour with transfers included. Travel in comfort by air-conditioned vehicle as you make your way through one of Tuscany’s most celebrated wine regions, famous for its cypress-lined roads, medieval villages, and world-class wines. Visit family-run wineries to learn about traditional and modern winemaking methods. Taste a variety of Chianti wines—paired with local specialties like olive oil, cheeses, and cured meats. Along the way, enjoy time to explore charming Tuscan villages surrounded by vineyards and breathtaking landscapes. With hotel pickup and drop-off in Florence, this private tour offers a seamless and personalized way to experience the flavors and beauty of Chianti.

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

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

The cellarmen of Casato Prime Donne are all women, including the winemaker, a unique feature in Italy that makes this winery a flag for pink winemaking. The frescoes among the barrels enrich the tour with information on the history of Montalcino and in the trinaia a representation of sounds and videos transports the visitor into the true spirit of the Borgo di Montalcino Finally, the art installations among the barrels, around the cellar and among the vineyards represent a permanent trace of the Casato Prime Donne Award as well as stand out as an example of Land Art

Enjoy an unforgettable day: let yourself be guided through the rolling hills and vineyards while admiring the beautiful Tuscan landscapes! Our tour will combine the perfect Brunello di Montalcino wine with our typical Tuscan cooking.  Thanks to this tour you will be able to appreciate wines and food and to learn more about our history and traditions: in two words, our Tuscan life style!

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and immerse yourself in Val d’Orcia! Our tour will combine the perfect Brunello di Montalcino wine with our typical Tuscan cooking. Thanks to this tour you will be able to appreciate wines and food and learn more about our history and traditions: in two words, our Tuscan life style! 10.00am Departure from Montalcino – Via Circonvallazione, 3 10.10am Arrive at MARTOCCIA . 11.45am Will reach PIOMBAIA – Biodynamic estate 1.00pm lunch in the historical villa, (4 coursed menù) After lunch, guided visit of the cellar 3.45pm We'll reach SAN CARLO estate. 3.15pm We move towards the historical cellar of CONTI COSTANTI, one of the oldest of Montalcino’s area. 7.00pm We’ll return to Montalcino – via Circonvallazione, 3

Our experienced sommelier will guide you through a tasting of four fine wines, including a white wine and three different red wines, each with its own unique characteristics and nuances. The red wines will surprise you with their colours from ruby red to deep dark red; you will learn to recognise the flavours, from the softest to the most tannic; you will discover the many aromas hidden in a wine, belonging to the families of spices, fruits, woods and many others such as leather and tobacco. White wine will refresh you and offer delicate and complex notes, also all to be discovered and analysed. The expert sommelier who will guide you through the tasting will not only introduce you to the wines, but also talk to you about the best pairings to make with food, local and otherwise. Once the tasting is over, it will be time for dinner, based on fresh, local and typical products, to be enjoyed in the beautiful SiChef Villa, framed by the Tuscan hills.

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.

Once you have booked the tour, you will be able to go to the rental point to pick up your bikes and leave with virtual navigation, which will accompany the route step by step. This circular e-bike tour (32km) starts from Montalcino, a medieval village famous for Brunello and views of the Val d’Orcia. The route crosses vineyards, secondary roads, compact dirt roads and rolling hills, offering views of the Tuscan countryside. The bikes are equipped with a phone holder, so you can follow the GPS directions on the application. Along the typical dirt roads you will encounter cypresses, isolated farms, scenic curves and landscapes that change color in every season. The climbs are regular and made more accessible by the support of the e-bike. One of the main stops is San Quirico d’Orcia, ideal for a break among historic alleys, squares and typical locals. The return to Montalcino completes a short but intense tour, perfect for discovering the most authentic Tuscany by e-bike

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

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.

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.

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