Top Chianti Tours by Duration in 2026

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.

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.

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.

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.

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

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.

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.

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

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.

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

Explore the enchanting Chianti region with a private tour that offers personalized wine tastings at family-run wineries and cultural experiences in historic towns. The tour provides a unique opportunity to visit two secluded vineyards, learn about the winemaking process, and enjoy a delicious lunch featuring local cuisine. With a knowledgeable driver, gain insider access to the best sights and hidden gems of Tuscany, ensuring an unforgettable experience tailored to your interests. Perfect for wine enthusiasts and culture lovers alike, this tour promises comfort and authenticity in every aspect. - Private wine tastings at charming family-owned wineries - Enjoy a local lunch at one of the vineyards - Flexible itineraries designed to suit your preferences

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!

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.

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.

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.

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

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.

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

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.

Original full day tour that will lead you into the most charming wine cellars which produce the king of Italian wines: Brunello di Montalcino. An experience among the vineyards and the grapes of Brunello to tell the story, the production secrets, the men who have made "prestigious" Montalcino and its territory. A good opportunity to learn about the fascinating world of wine: guided tours, tastings and, above all, the chance to make a very quiet trip, without having the worry about the breathalyser after sipping a glass of good wine.

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.

Enjoy an unforgettable day: let us guide you through the rolling hills and vineyards to discover the local flavors and scents Montalcino is a land of great wines, but perhaps not everyone knows that it also hosts many other excellences. It is a territory with a vast production of extra virgin olive oil, honey, flour and ancient grains, white, black and marzuolo truffles, excellent cold cuts and cheeses and not least the expensive saffron, the oldest product of Montalcino