Top Chianti Tours, Sightseeing & Cruises

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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 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.

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

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.

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 ...

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 beautiful landscapes of Montalcino and the Val d'Orcia with a convenient e-bike or gravel bike rental. Enjoy the freedom to explore at your own pace, equipped with a Garmin navigator with preloaded maps for a self-guided adventure. Ideal for independent travelers who want to immerse themselves in the beauty of Tuscany. - Rent an e-bike or gravel bike for maximum flexibility - Navigate effortlessly with a Garmin device and preloaded maps - Perfect for solo explorers and adventure lovers - Enjoy the picturesque landscape of Montalcino at your leisure

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

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.

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

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.

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.