Tuscany’s Chianti region delivers Italy’s most rewarding wine experiences without the tourist crowds you’ll find elsewhere. The area’s top tours combine wine education with authentic tastings in family-run estates. Three standout options deserve special mention: The Organic Winery Tour offers an intimate look at sustainable winemaking methods and generous tastings. The Brunello Vineyards Tour takes you through some of Italy’s most prestigious wine estates. For active travelers, the Chianti eBike Tour lets you pedal through scenic backroads while visiting two distinctive wineries. All include expert guides who explain wine-making techniques in clear, practical terms. These carefully selected tours below represent the best of Chianti’s wine country.
Key Points
- Organic Winery Tour and Tasting: A 1.5-hour personalized experience with a guided vineyard and winery exploration, and a tasting of 3-6 organic wines.
- Greve in Chianti Wine Tasting: A 2-hour immersive tour at a family-run winery, featuring a tasting of four Chianti Classico red wines paired with fresh cheeses and salami.
- Monterinaldi Castle Wine Tasting: A guided journey through wine cellars with tastings of three distinct wines and a dessert vinsanto, accompanied by a 3-course Tuscan lunch.
- Brunello Vineyards Tours: A 3-hour small-group tour visiting two local wineries in Montalcino, focusing on Rosso and Brunello wines, led by an English-speaking guide.
- E-Bike Tour in Chianti: A half-day adventure exploring Chianti’s landscapes on electric bikes, including a visit to a local winery for a tasting and lunch.
Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
What better way to take in the renowned Chianti region than a guided tour and tasting at an organic winery? This 1.5-hour experience in the Chianti Classico area offers a deep dive into the art of winemaking.
Visitors can explore the vineyards and winery, learning about the local methods from knowledgeable guides. The highlight is the wine tasting session, where guests sample 3-6 organic wines accompanied by freshly baked bread and olive oil produced on-site.
With a maximum group size of 14, this tour provides an intimate and personalized experience. Reviewers consistently praise the passionate staff, especially the guide Francesco, for their engaging presentations.
The stunning Tuscan scenery and high-quality wines also receive glowing feedback. While the remote location can make the winery challenging to find, those who make the journey are rewarded with an unforgettable glimpse into the heart of Chianti.
At $42.79 per person, this tour is a must for wine enthusiasts visiting the region.
Read our full review: Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area Review
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Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
This 9-hour private wine tour from Livorno port provides an immersive exploration of the renowned Chianti wine region and the picturesque Tuscan countryside.
Travelers will embark on a scenic drive, passing the Santa Croce church and local shops in Greve-in-Chianti before visiting a prominent local winery for a private tour and tasting. Here, they’ll sample Chianti wine and top-quality Tuscan olive oil, learning about the winemaking process.
Guests have the option to enjoy a traditional Tuscan lunch at an additional cost. The tour’s private nature ensures a personalized experience, with transportation provided by an air-conditioned sedan or minivan.
While the tour isn’t wheelchair accessible, it offers accommodations like foldable wheelchairs and baby seats. Travelers can also benefit from the tour’s worry-free guarantee, which includes timely port return and transportation to the next port if the ship departs.
With an overall 5.0 rating from 43 reviews, this tour is a highly recommended way to explore the Chianti countryside.
Read our full review: Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour Review
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Greve in Chianti Wine Tasting and Winery Tour
Nestled in the heart of the renowned Chianti wine region, the Greve in Chianti Wine Tasting and Winery Tour offers travelers an immersive experience to explore the rich winemaking traditions of this picturesque area.
With over 110 reviews and a 91% recommendation rate, this tour provides a behind-the-scenes look at an organic, family-run winery in Greve. Guests can expect to learn about the production of Chianti Classico, made from the renowned Sangiovese grapes, and sample four different red wines paired with fresh cheeses and salami.
Located just 30 km from Florence and accessible within a 75-minute drive from the airport, the tour lasts approximately 2 hours and accommodates a maximum of 15 people per booking.
While the tour receives largely positive feedback for its knowledgeable host and scenic views, some guests have noted issues with group dynamics and perceived value.
Read our full review: Greve in Chianti Wine Tasting and Winery Tour Review
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Discovering Chianti, E-Bike Tour – Daily Experience
Seeking an unforgettable adventure through the picturesque Chianti region? Look no further than the Discovering Chianti, E-Bike Tour – Daily Experience. This half-day tour offers travelers a chance to explore the stunning landscapes and historic landmarks of the Chianti area on an electric bike.
With a maximum group size of 8, this tour provides a personalized and intimate experience. During the scenic e-bike ride, you’ll visit the charming Castello di Montefioralle and the Abbey of Badia di Passignano, taking in the breathtaking views along the way.
At a local winery, you’ll indulge in a delicious lunch and wine tasting, enjoying the region’s renowned culinary delights.
Suitable for travelers in reasonable physical condition, the tour includes all necessary equipment, bottled water, and a knowledgeable guide to ensure a safe and enjoyable experience.
With 20 reviews and a 100% recommendation rate, this is a must-do activity for anyone seeking to discover the beauty and charm of the Chianti region.
Read our full review: Discovering Chianti, E-Bike Tour – Daily Experience Review
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Brunello Vineyards Bus Tour
The Brunello Vineyards Bus Tour offers a 3-hour small-group wine experience in the heart of Montalcino, Italy.
Led by an English-speaking local guide, the tour takes visitors to two renowned local wineries for in-depth tours and tastings of the region’s famous Rosso and Brunello di Montalcino wines.
Travelers are transported in a comfortable 8-seat Mercedes minivan, ensuring a personalized and intimate experience.
At the wineries, they’ll learn about the unique terroir and production methods that give these bold, full-bodied wines their distinctive character.
The tour includes hotel pickup from selected properties, making it convenient for guests.
With a 100% recommendation rate from past participants, the Brunello Vineyards Bus Tour is an excellent choice for wine enthusiasts seeking to enjoy the rich winemaking traditions of Montalcino.
The minimum booking requirement is two adults, and the maximum group size is six travelers, ensuring a tailored and exclusive experience.
Read our full review: Brunello Vineyards Bus Tour Review
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Winery Tour & Gourmet Tasting in Montalcino
Situated in the heart of Chianti, the Winery Tour & Gourmet Tasting in Montalcino offers visitors an immersive journey through the region’s renowned winemaking heritage.
This highly-rated experience, with 100% traveler recommendation, promises a delightful exploration of the area’s iconic Brunelli and other remarkable wines.
During the tour, guests will savor six gourmet appetizers expertly paired with six different wine varieties from Montalcino.
The guided experience takes place at the Corte Pavone Winery, nestled amid the picturesque countryside.
Attendees can expect a warm welcome, impeccable service, and knowledgeable insights from the guides, Andrea and Emma.
Priced at $85.60 per person, the tour includes all fees and taxes, as well as bottled water to complement the wine tastings.
Accessibility is limited, as the experience isn’t wheelchair-friendly, though strollers and service animals are permitted.
With a maximum group size of 25 travelers, the tour provides an intimate and personalized encounter with Montalcino’s winemaking tradition.
Read our full review: Winery Tour & Gourmet Tasting in Montalcino Review
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Brunello E-Bike Tour
Set out on a captivating Brunello E-Bike Tour through Chianti’s picturesque countryside. This half-day adventure showcases the region’s natural beauty and renowned winemaking.
Pedal on unpaved roads towards local Tuscan vineyards, culminating in a wine tasting at the Abbey of Sant’Antimo. Sample three wines, including the renowned Brunello di Montalcino. Afterward, explore the charming medieval town of Montalcino.
The tour includes the use of an electric bicycle and helmet, a light lunch with cheese and cold cuts, and a local guide to lead the way. Additional perks like a bottle of water, snacks, and alcoholic beverages are also provided.
With a 5.0-star rating from 8 reviews, this private tour offers an immersive experience for moderate fitness levels. Confirmation is subject to availability, and free cancellation is allowed up to 24 hours prior.
Don’t miss this opportunity to discover Chianti’s highlights on two wheels.
Read our full review: Brunello E-Bike Tour Review
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Montalcino Wine Tour
Explore the renowned wines of Montalcino on this comprehensive tour. Venture through the picturesque Chianti region and visit four renowned wineries, where you’ll enjoy guided tastings and learn about the area’s renowned Rosso and Brunello di Montalcino varietals.
The tour accommodates a maximum of 8 travelers, ensuring an intimate and personalized experience. Savor a light lunch paired with these prestigious wines, and indulge in snacks and alcoholic beverages throughout the day.
The air-conditioned vehicle ensures a comfortable journey, while all fees and taxes are included in the $374.51 per person price. Although the tour isn’t wheelchair accessible, it’s stroller-friendly and near public transportation, making it accessible for most travelers.
With 6 reviews and a 4.2/5 rating, this Montalcino wine tour promises an immersive and educational exploration of the region’s finest vintages. The tour starts at 10:00 am and ends back at the meeting point in Montalcino, providing a well-rounded and convenient experience for wine enthusiasts.
Read our full review: Montalcino Wine Tour Review
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Discovering Chianti: Sunset Ebike Tour and Dinner
A 3-hour eBike tour through the picturesque Chianti region of Tuscany offers travelers a unique opportunity to discover the area’s stunning countryside.
Suitable for novice and expert cyclists alike, the customizable tours cater to a range of ages, skill levels, and group sizes, ensuring an enjoyable experience for all. Along the way, you will be treated to panoramic views of the rolling hills and vineyards that define the Chianti landscape.
The culinary experience is equally impressive, with a delectable aperitif, fine local wines, and a rich platter of cold cuts and cheeses awaiting at the end of the tour.
The meeting point is located in Barberino Tavarnelle, with the closest airports being Florence Peretola and Pisa International. While the tour isn’t wheelchair accessible and not recommended for those with certain medical conditions, it can accommodate up to 6 travelers, with confirmation provided within 48 hours of booking.
Priced at $176.55 per person, this eBike tour through Chianti promises an unforgettable exploration of Tuscany’s countryside and culinary delights.
Read our full review: Discovering Chianti: Sunset Ebike Tour and Dinner Review
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Radda in Chianti: Wine Tasting Tour With Lunch at the Castle
Tucked away in the heart of Chianti’s picturesque rolling hills, the Monterinaldi Castle opens its doors to wine enthusiasts seeking an immersive tasting experience.
This highly-rated wine tour, with an overall 4.5-star rating on Viator and Tripadvisor, takes visitors on a guided journey through the castle’s wine cellars, led by a knowledgeable sommelier.
Travelers can indulge in tastings of three distinct wines and a dessert vinsanto, as they learn about the region’s winemaking traditions.
The experience is complemented by a 3-course traditional Tuscan lunch served in an 18th-century villa on the castle’s tranquil grounds, where live turtles can be spotted.
While most guests rave about the wonderful wine selection and delicious food, some note that the tour guides may occasionally rush through the experience or lack full engagement.
Read our full review: Radda in Chianti: Wine Tasting Tour With Lunch at the Castle Review
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Grand Tour of Pienza, Montalcino, Montepulciano + Wine and Cheese Tasting
Travelers seeking a comprehensive Tuscan experience can embark on a guided tour that showcases the charming towns of Pienza, Montalcino, and Montepulciano.
The walking tour includes a visit to the UNESCO World Heritage Site of Pienza, known for its 16th-century Renaissance architecture. The guided exploration also encompasses Montepulciano’s grand palaces and Pienza’s historical significance.
Enhancing the journey, the tour offers a tasting of the renowned Brunello de Montalcino wine at a local winery, as well as a sampling of pecorino cheese. The private tour is led by a professional guide-sommelier, and the cost includes snacks and wine tasting fees.
However, transportation isn’t provided, though it can be arranged for an additional fee.
The tour operates daily from 9 AM to 6 PM, from August 28, 2019, to February 9, 2026. It accommodates a maximum of 10 people and is wheelchair and stroller accessible.
Cancellation is free up to 24 hours before the experience, with a cost of $374.51 per group.
Read our full review: Grand Tour of Pienza, Montalcino, Montepulciano + Wine and Cheese Tasting Review
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The Sum Up
The Chianti region of Tuscany offers a variety of exceptional wine tours and tastings. From organic wineries to e-bike excursions, visitors can explore the stunning countryside and sample the renowned Chianti wines. Whether you’re a wine enthusiast or simply seeking an immersive Tuscan experience, the tours in Chianti provide an excellent opportunity to explore the rich culture and flavors of this iconic Italian wine region.