Wine tour in Chianti and visit of San Gimignano for small groups

A Taste of Tuscany: Small-Group Wine Tour in Chianti & San Gimignano

This small-group wine tour from Florence offers an authentic slice of Tuscany, combining a trip to the iconic medieval town of San Gimignano with a scenic drive through the Chianti countryside. The experience is tailored for those who love good wine, beautiful landscapes, and delicious food, all delivered in a cozy, intimate setting.

What stands out most is the combination of a guided visit to San Gimignano’s historic streets—complete with a climb up the Torre Grossa for panoramic views—and the chance to sip six carefully chosen wines at a traditional farm. Our favorite part? The homemade Tuscan lunch that pairs perfectly with the wines, giving you a true taste of local flavors.

One thing to consider is the tour duration—around five hours—which means packing plenty into a relatively short window. It’s best suited for travelers seeking a relaxed yet immersive experience of Tuscany’s culinary and vinicultural delights, especially those who appreciate expert guides and small groups that foster a personal touch.

Key Points

• Intimate small-group setting ensures more personalized attention and a relaxed atmosphere.
• Authentic Tuscan lunch with locally sourced ingredients and expertly paired wines.
• Visit to San Gimignano offers stunning panoramic views and a glimpse into medieval history.
• Six wine tastings including Chianti, Super Tuscan, and Vernaccia di San Gimignano.
• Beautiful drives through the Chianti countryside, perfect for memorable photos.
• Expert guide (noted for being knowledgeable and attentive) enhances the experience.

Discovering San Gimignano: The Medieval Marvel

Our tour kicks off with a short drive from Florence to San Gimignano, famously known as the “Town of Fine Towers.” Once boasting over 70 towers designed as symbols of wealth and power, only 14 remain today, creating a skyline that looks like a fairy-tale village. As you stroll through its narrow, cobbled streets, you’ll be transported back in time, surrounded by medieval architecture and artisan shops.

One of the highlights is climbing the Torre Grossa, the tallest tower in San Gimignano, which offers sweeping views across the Tuscan hills and vineyards. It’s a must-do for photography lovers, providing that postcard-perfect backdrop. During your wanderings, you’ll also get to sample some of Italy’s best gelato at the Piazza della Cisterna—an unmissable treat that many reviews point out as a highlight.

San Gimignano is also renowned for its saffron and Vernaccia di San Gimignano wine, which you might find tasting as delightful as the town itself. The craftsmanship of local artisans is visible everywhere—from jewelry to ceramics—making it a vibrant open-air museum.

According to recent reviews, visitors appreciated the guided insights into local produce and the opportunity to learn about the town’s historical significance. One guest mentioned, “Our guide Michel was unbelievably knowledgeable,” which speaks to the quality of the tour leadership.

Scenic Drive & Panoramic Vineyards

After exploring San Gimignano, the journey continues along one of Tuscany’s most picturesque routes, winding through rolling hills and vineyards. This stretch is perfect for capturing the iconic Tuscan landscape—think golden fields, cypress-lined roads, and rustic farmhouses. It’s an ideal spot for photos or simply soaking in the scenery.

The highlight here is arriving at a traditional Tuscan farm, where the real flavor of the region comes alive. This is a working farm, not just a tourist stop, and the atmosphere is warm and genuine. The farm’s setting allows you to appreciate the agricultural roots of the wines and foods you’ll enjoy later.

Authentic Tuscan Lunch & Wine Tasting at Agricola Poggio Ai Laghi

The farm hosts a delicious three-course lunch, featuring bruschetta, homemade pasta, cured meats, pecorino cheese, and desserts—all crafted with locally sourced ingredients. Many reviews point out how fresh and flavorful the meal was, elevating the experience from mere tasting to a full culinary immersion.

And then comes the wine tasting—an essential part of the tour. You’ll sample five wines, including Chianti, Chianti Riserva, Sangiovese, Vernaccia, and a Super Tuscan. The wines are thoughtfully selected to showcase the diversity and quality of the region’s production, and the guide provides helpful insights into each variety.

What sets this experience apart is the pairing of food and wine. The farm staff often explain how local ingredients and winemaking techniques contribute to the distinct flavors. One reviewer noted that the experience was “more than just a meal; it was a complete Italian experience,” which captures the essence of this tour.

Who is This Tour Perfect For?

This tour is ideal for those who want a balanced mix of history, scenery, and wine tasting without it taking up a full day. It’s perfect if you’re seeking an intimate, authentic experience with knowledgeable guides and delicious local cuisine. It’s also well-suited for couples, small groups, or anyone eager to explore Tuscany at a relaxed pace.

Keep in mind, with a maximum of 7 travelers, you’ll enjoy plenty of individual attention, but this also means booking in advance (most travelers book around 95 days ahead). The 5-hour duration means you’ll have time to enjoy each stop without feeling rushed, but be prepared for a fairly full schedule.

Practical Details & Value

The tour costs $242 per person, which might seem high at first glance, but considering the inclusions—transportation, a three-course lunch, five wine tastings, bottled water, and an expert guide—it offers good value for an immersive Tuscan experience.

The vehicle is air-conditioned, making the journey comfortable even in warmer months. Plus, the small group size ensures a cozy, engaging atmosphere, often leading to more genuine interactions and tips from your guide. The tour starts early at 9:00 am, giving you the entire morning to soak in the sights and flavors of Tuscany.

While the tour does not include a dedicated guide for the stops (though you can request one), the driver/guide, Michel, is praised for his vast knowledge and attentiveness, making the journey both informative and enjoyable.

Final Thoughts

This small-group wine tour manages to strike a fantastic balance between history, scenery, and gastronomy. It’s a well-rounded experience for those who want to see the real Tuscany, taste excellent wines, and enjoy a delicious homemade meal—all in an intimate setting.

If you’re after a thoughtfully curated tour that offers genuine insight into Tuscan life and winemaking, and if you appreciate smaller groups for a more personal touch, this is a top choice. It’s especially perfect for travelers who want to avoid large crowds but still crave a comprehensive, memorable taste of Tuscany.

FAQ

Is this tour suitable for all ages?
Most travelers can participate, but it’s primarily designed for adults interested in wine, food, and historical sights. Children are typically not included, and the focus is on adult tastings.

How long is the tour?
The entire experience lasts about 5 hours, starting at 9:00 am and ending back at the meeting point, making it a manageable half-day activity.

Are the wine tastings included in the price?
Yes, you’ll enjoy five wine tastings—Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Super Tuscan—paired with the meal.

Can I request an English-speaking guide?
The tour uses a local expert driver, and while a pro guide isn’t included by default, you can request one one week in advance for an additional fee.

What should I wear?
Comfortable clothing and shoes suitable for walking in a medieval town and farm setting are recommended. Bring sun protection or an umbrella, depending on the weather.

Is transportation provided?
Yes, an air-conditioned vehicle transports you from Florence and through the scenic Tuscan countryside, making the experience hassle-free.

In summary, this small-group Chianti and San Gimignano wine tour offers an excellent mix of history, scenery, and authentic Tuscan flavors. It’s perfect for those wanting a personalized experience, rich in wine, good food, and stunning views—all wrapped up in a relaxed, intimate atmosphere. Whether you’re a seasoned wine lover or simply eager to taste the essence of Tuscany, this tour is a compelling choice.