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Explore the heart of Chianti Classico with visits to three renowned wineries, a scenic lunch, and tastings of over 15 wines on this small-group tour from Florence or Siena.
Discover the essence of Chianti Classico wines on this engaging small-group tour that departs from Florence or Siena. Priced at approximately $274.53 per person, this tour offers a full day of wine tasting, scenic drives, and a delicious Tuscan lunch. With a maximum of 8 travelers, it promises an intimate experience with personalized attention from the guide. The tour is highly recommended, with a 5.0-star rating from 29 reviews, and is booked on average 78 days in advance.
This tour highlights the rich winemaking tradition of the Chianti region by visiting three different wineries including one of the oldest and most prestigious in Monteriggioni, tasting more than 15 wines including Grand Selezione, Riserva, and Supertuscan. The full-day experience also features a lunch in Castellina In Chianti, where you can enjoy local dishes paired with various wines and sample other regional products like EVO oil and Balsamic Vinegar. The entire journey is complemented by round-trip transport in an air-conditioned vehicle, making it a seamless way to explore Tuscany’s famed wine country.
While the tour boasts many strengths, it’s important to note that the experience can be affected by guide language skills, as one review mentions a guide with limited English. However, most guests find the small group size and scenic countryside highly rewarding, making this tour ideal for wine enthusiasts and those wanting a relaxed, personalized day in Tuscany.

The tour begins with a visit to Monteriggioni, a village home to one of the oldest and most famous wineries in the Chianti region. Here, guests can appreciate the historic setting while exploring the winery’s facilities and tasting some of their best wines. This 2-hour stop is free of admission charges and sets the tone for the day ahead, emphasizing the region’s longstanding wine traditions.
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Next, the tour moves along the Chiantigiana road, renowned for its panoramic vineyards. At the second winery, admission is included, and visitors are treated to a tasting of premium wines such as Grand Selezione, Riserva, and Supertuscan. This stop combines wine tasting with a scenic drive, allowing guests to admire the rolling hills and lush landscapes characteristic of Tuscany.

The most leisurely part of the day takes place in Castellina In Chianti, where a full four-hour stop enables guests to enjoy a specially prepared lunch at a local winery. Each dish is paired with a different wine, and guests have the chance to sample other regional products like extra virgin olive oil and Balsamic Vinegar. This meal offers a true taste of local flavors within a beautiful Tuscan setting, making it a highlight for food and wine lovers alike.

Before lunch, the tour allows time to visit a village in Chianti, giving guests a chance to stroll through charming streets and soak in the rustic atmosphere. The visit to Castellina In Chianti combines cultural exploration with culinary indulgence, making the stop both relaxing and enriching.

All transportation is in an air-conditioned vehicle, ensuring comfort as you travel through vineyard-covered hills. Pickup is offered, simplifying access from Florence or Siena, and the small group size maximizes interaction with the guide while minimizing crowding.
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The small-group format, limited to 8 travelers, allows for more personalized guidance and flexibility. The inclusion of lunch, combined with multiple winery visits and a focus on Chianti Classico’s top wines, offers excellent value for wine connoisseurs and casual enthusiasts alike. Plus, the scenic drives and visits to historic villages make this experience more than just wine tasting—it’s a curated journey through Tuscany’s heartland.

One aspect to keep in mind is the guide’s language proficiency, as one review highlights difficulties with communication. However, most guests find the personalized service compensates for this, especially given the small group size. The tour is suitable for most travelers, but those with specific dietary requirements should advise in advance to ensure meal options meet their needs.
This experience is perfect for wine lovers seeking a deeper understanding of Chianti Classico wines. It suits those interested in scenic countryside and Tuscan villages, as well as anyone wanting a relaxed, guided day outside the city. The lunch and tastings provide a comprehensive taste of the region’s best offerings, making it an ideal choice for a full-day escape from Florence or Siena.
The Heart of Chianti Classico tour offers a well-rounded introduction to Italy’s most famous wine region. With visits to three historic wineries, tastings of more than 15 wines, and a delicious paired lunch, it combines scenery, culture, and cuisine in one seamless experience. The small group setting ensures a more personal touch, while the scenic drives and village visits enrich the journey.
While guide language skills can vary, most will find the quality of wine, beautiful landscapes, and authentic Tuscan cuisine make this tour stand out. It’s best suited for wine enthusiasts or anyone craving an immersive, relaxed day exploring Tuscany’s renowned vineyards.
“Best time in Tuscany!! Our driver Mikel went above a beyond to make our day special!! Both wineries were unique and personal. We will be back!!”
Is transportation included in this tour?
Yes, round-trip transport from Florence or Siena is included, in an air-conditioned vehicle.
What is the duration of the tour?
The tour lasts from 1 to 8 hours, with the lunch stop in Castellina In Chianti being the longest part, at 4 hours.
How many wineries are visited?
Guests visit three wineries, including one of the oldest in Monteriggioni and a scenic stop on the Chiantigiana road.
Are the wine tastings limited to red wines?
No, the tastings include more than 15 wines, including Grand Selezione, Riserva, and Supertuscan, which are mostly red varieties.
Is vegetarian lunch available?
Yes, vegetarian options are available; guests should advise at booking.
What products can I sample during lunch?
The lunch includes wines paired with dishes and options to sample EVO oil, Balsamic Vinegar, and dessert wines.
What should I wear for the tour?
Comfortable clothing suitable for walking and outdoor scenery is recommended, though specific dress code details are not provided.
Can I cancel this tour?
Yes, free cancellation is available up to 24 hours in advance for a full refund.
Is this tour suitable for children?
Most travelers can participate, but the data does not specify age restrictions, so families should consider the pace and length of the day.
How far in advance should I book?
The tour is most frequently booked 78 days in advance, suggesting early reservation is wise, especially during peak seasons.