From San Gimignano: Chianti Wine tour with 2 wineries

If you’re dreaming of lush vineyards, rolling hills, and a taste of authentic Tuscan life, a guided Chianti wine tour from San Gimignano might be just what you need. This experience, carefully curated by Italy on a Budget Tours, promises a five-and-a-half-hour journey through one of Italy’s most famous wine regions, complete with visits to two wineries, tastings of nine different wines, and plenty of local products.

What stands out most? We’re fans of the expert guidance that helps you truly understand the wines and foods you’re sampling, plus the chance to enjoy some of the most beautiful countryside in Tuscany. That said, be prepared for a group experience that’s on the larger side during peak season, and remember that this tour doesn’t include lunch—so plan accordingly if you’re hungry.

This tour is perfect for curious wine lovers, foodies, and anyone who wants to combine scenic views with a relaxed tasting experience. If you’re eager to explore the Chianti region without worrying about driving, this well-organized trip offers good value and authentic insights.

Key Points

• Authentic experience: Guided by a knowledgeable local, you get a true taste of Tuscany’s wine culture.
• Tasting variety: Nine different wines, plus olive oils and balsamic vinegar, showcase regional flavors.
• Educational aspect: Includes a professional wine tasting lesson that enhances understanding and appreciation.
• Beautiful scenery: The tour offers stunning views of the Chianti countryside, ideal for photography or just soaking in the landscape.
• Convenience: Roundtrip transportation from Poggibonsi means no fuss about navigating or parking.
• Limited lunch options: No included meal, so consider eating beforehand or bringing snacks.

You can check availability for your dates here:

An In-Depth Look at the Chianti Wine Tour from San Gimignano

Starting Point and Transportation

The tour begins in Poggibonsi, conveniently located near San Gimignano, where you’ll meet your guide at the Tuscany on a Budget Tours office. Parking is free—an underrated perk when dealing with busy tourist hubs. From here, a comfortable minivan or bus whisks you off into the heart of the Chianti countryside, a region famous worldwide for its scenic vineyards and medieval towns. The ride itself sets the tone—relaxing yet exciting, as you leave the bustling towns behind for the tranquil rolling hills.

The First Stop: The Tuscany Wine Tasting School

Your first destination is a local wine tasting school. It’s more than just sipping wine; it’s an opportunity to learn what makes Chianti wines special. The guide leads an engaging and professional lesson, explaining the differences between types of wine and how they’re made. You’ll taste four wines here, including the Chianti Classico D.O.C.G. and a Super Tuscan, which can sometimes surprise visitors with their bold flavors and complex character.

But it’s not just wine. You’ll also sample 30-year-old balsamic vinegar and extra virgin olive oil, both produced locally. These tastings are complemented by snacks that help balance the flavors and keep your palate ready for the next round. One reviewer noted, “The tasting of the balsamic vinegar was a revelation—I could tell the difference immediately.” This part of the tour isn’t just fun; it’s an insightful education for anyone interested in Tuscan culinary traditions.

The Second Stop: A Local Winery

Next, you’ll visit a working winery in the Chianti area. Here, the focus shifts from tasting to understanding. The guided tour includes a walk through the vineyards, where you’ll see the grape varieties and learn about the winemaking process. The guide’s knowledge shines here, explaining the nuances of each wine you sample.

Expect to taste three wines during this visit: the Vernaccia white wine, a rosé, and a Chianti colli senesi D.O.C.G.. The setting is picturesque—vines stretching into the distance, with the rustic charm of a traditional Tuscan winery. Reviewers have appreciated the personal touch, with one commenting, “The guide’s explanations made the wines even more enjoyable, and the setting was breathtaking.”

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San Gimignano: A Quick Stop

Before heading back, you’ll have a brief stop in San Gimignano, famous for its medieval towers and charming streets. It’s a good chance to stretch your legs, snap some photos, and soak in the historic atmosphere. Since the tour isn’t spending much time here, it’s ideal for a quick stroll rather than extensive sightseeing.

Returning and Reflection

The journey concludes back at your starting point in Poggibonsi. The entire experience lasts about 5.5 hours, providing a well-rounded, relaxed day out. The small group setting offers a more intimate experience, though during high season, larger groups are common.

What’s Included and What’s Not

The tour’s price includes roundtrip transportation, an English-speaking guide, visits to two wineries, up to eight wine tastings, and up to three olive oil tastings. Plus, snacks are provided to complement the tastings.

However, lunch is not included, so plan accordingly—perhaps enjoy a hearty breakfast or pack a picnic for after the tour if you want to keep your energy up. The flexible cancellation policy (full refund if canceled 24 hours in advance) adds peace of mind for spontaneous travelers.

Who Will Love This Tour?

If you’re eager to learn about Tuscan wines and foods in a relaxed setting, this tour offers great value. It’s especially suited for those who appreciate guided experiences that blend education with scenic beauty. Foodies will enjoy the olive oil and balsamic tastings, while wine enthusiasts will savor the variety of samples.

Keep in mind, the tour isn’t designed for children under 18 or pregnant women, as it involves alcohol tastings. Also, if you’re a solo traveler, the small group setting can be a plus, fostering interaction and personalized attention.

Final Thoughts

This Chianti wine tour offers an authentic slice of Tuscany’s famous landscape and gastronomy. The combination of scenic views, expert guides, and diverse tastings makes it a solid choice for those wanting to enjoy the region without the hassle of driving or planning multiple visits.

The tour’s strong points include the knowledgeable guides, the opportunity to taste multiple authentic wines and foods, and the chance to soak in some of Italy’s most picturesque countryside. While it doesn’t include a full meal, the tasting experience compensates with quality and variety that many travelers find worth the price.

In short, this experience suits curious travelers who want a comprehensive, enjoyable introduction to Chianti’s wines and culinary heritage. Ideal for those who value quality guidance, scenic beauty, and flavorful discoveries.

Frequently Asked Questions (FAQs)

Is transportation included in the tour?
Yes, roundtrip transportation is provided from Poggibonsi, making it easy to relax and enjoy the scenery without worrying about driving.

What is the duration of the tour?
The tour lasts approximately 5.5 hours, which is enough time to visit two wineries, enjoy tastings, and explore a bit of San Gimignano.

Are the group sizes small?
The tour offers small group options, but during high season, it might be a larger group—up to 60 people—so it’s not a private experience.

Is lunch included?
No, lunch is not included. You might want to eat beforehand or plan to enjoy local food after the tour.

Can children or pregnant women join?
No, the tour is not suitable for children under 18 or pregnant women due to alcohol tastings.

What is the focus of the guided experience?
You’ll learn about wine and olive oil production, taste a variety of regional products, and gain insights from a local guide—making it both educational and delicious.

Do I need to book in advance?
Yes, it’s recommended to reserve your spot, especially in high season. You can cancel up to 24 hours in advance for a full refund, providing flexibility.

This Chianti wine tour combines scenic beauty, local flavors, and expert guidance into a memorable half-day in Tuscany. Whether you’re a first-time visitor or a seasoned wine lover, it offers a genuine taste of what makes this region special.

You can check availability for your dates here: