EXCLUSIVE Wine Tour in Chianti & San Gimignano (Lunch & Wine Tasting included)

An Authentic Day in Tuscany: Private Chianti & San Gimignano Wine Tour

If you’re craving a taste of Tuscan charm, this private tour from Florence is perfect. Priced at just over $288 per person, it lasts about six hours and offers a well-balanced mix of scenic drives, medieval towns, and wine country indulgence. Led by a professional driver—who becomes your personal guide—you’ll explore the Chianti hills, visit the medieval town of San Gimignano, and enjoy a delicious Tuscan lunch paired with wines from local vineyards.

Two things we really love about this experience: First, the personalized nature of the tour. Being limited to your group means more attention, less rush, and a chance to ask plenty of questions. Second, the combination of cultural exploration with tasting—you get to stroll through San Gimignano’s historic streets and then indulge in wine and food, making it a complete taste of Tuscany.

A possible consideration? While the tour is highly praised for its authenticity and guides, some may find the one-hour free time in San Gimignano a bit brief if you want to explore every corner. Also, if you’re not a fan of organized tours, this might feel a little structured for your taste.

This tour is ideal for travelers who want a relaxed, intimate experience that combines beautiful scenery, history, and gastronomy. Perfect for those who appreciate good wine, authentic local food, and scenic drives, especially if you prefer a more personalized touch rather than large group excursions.

Key Points

• Private experience offers personalized attention and flexibility.
• Visit San Gimignano—a medieval hill town famous for its towers and saffron.
• Includes a traditional Tuscan lunch with multiple courses and wine tastings.
• Vineyard visits showcase Chianti, Vernaccia, and Super Tuscan wines.
• Scenic drives through Chianti provide stunning views of hills, vineyards, and olive groves.
• Authentic farm visit offers insight into organic wine-making and local products.

Exploring the Heart of Tuscany: A Deep Dive into the Tour

The Scenic Drive and Pickup

Starting in Florence, your driver—who is also your guide—meets you at your hotel, B&B, or private apartment. From there, the journey kicks off with a comfortable, air-conditioned vehicle as you traverse one of Italy’s most famous wine routes. The drive itself is a highlight: rolling olive groves, cypress-lined roads, and medieval villages whiz past your window, offering countless photo opportunities.

The early morning start at 9:00 am means you’ll be traveling when the Tuscan landscape is at its most tranquil, with soft morning light illuminating the hills and vineyards. The attention to comfort is evident, and bottled water is provided for refreshment along the way.

San Gimignano: Towering Medieval Charm

Your first stop is San Gimignano, known as the “Town of Fine Towers.” With just about an hour to explore, you’ll have time for a quick but meaningful wander through its cobblestone streets. This UNESCO World Heritage site is a favorite for good reason: its skyline is defined by medieval towers that once signified wealth and power. Today, they create a stunning silhouette against the sky.

You can stroll through the main square, taking in sights like the Collegiata di Santa Maria Assunta, and perhaps indulge in the world’s best ice cream at Gelateria Dondoli, praised by many visitors. The town’s craftsmen and artisans keep alive centuries-old traditions, so you might find charming shops selling local saffron, ceramics, or handmade jewelry.

While one hour might seem brief, it’s enough to get a sense of the town’s atmosphere and take some scenic photos. For those eager for more, the reviews highlight the charm and authenticity, with one traveler noting, “Our tour guide Andrea made us feel like we were visiting an old friend.”

Lunch at Podere La Marronaia- Le Colonne

After San Gimignano, your next stop is a family-run organic farm and winery—a true highlight of the day. This biodynamic estate offers an intimate look at Tuscan winemaking. Here, you’ll enjoy a three-course lunch featuring bruschetta, lasagna or homemade pasta, cured meats, pecorino cheese, and dessert.

The lunch isn’t just about eating; it’s about experiencing local flavors in a setting that echoes Tuscany’s rural charm. The reviews reveal that the food is delicious, with many praising the authenticity and quality of the dishes. One reviewer said, “The food and the wine at the winery were absolutely amazing,” emphasizing how satisfying and genuine the experience feels.

During your meal, you’ll participate in a wine tasting featuring Chianti, Chianti Riserva, Sangiovese, and Vernaccia. The farm also offers a tasting of extra virgin olive oil, adding to the sensory experience. The five wine tastings are carefully curated to showcase the region’s best.

Vineyard and Wine Tasting Experience

The heart of the tour is the wine tasting on the farm, which provides a perfect opportunity to learn about Tuscan wine production and pairing techniques. The reviews repeatedly praise the knowledgeable guides and the quality of wines, making this a real treat for wine lovers.

The tasting includes local varietals, with many visitors mentioning that the wines are excellent, and complement the food perfectly. The guide’s insights and friendly approach make the wine tasting both educational and enjoyable.

The Value of a Private, Guided Experience

This tour’s private setup means the experience is tailored to your pace. The driver, often praised as friendly and knowledgeable, becomes more than just a driver—he’s an informal guide, sharing stories and answering questions, which elevates the overall experience.

The cost of around $288 per person might seem high for some, but considering the personalized service, exclusive visits, and quality food and wine, many find it offers great value. You’re paying for authenticity, comfort, and expert guidance—not just a rushed sightseeing bus.

Who Will Love This Tour?

Travelers who enjoy good food, wine, and scenic drives will find this experience ideal. It’s especially well-suited for those who value small-group or private outings, and want to avoid large bus crowds. History buffs will appreciate the visit to San Gimignano, while foodies will relish the homemade Tuscan dishes and wine tastings.

The reviews highlight how guides like Stefano and Andrea make the day special, blending knowledge with warm personalities—a great bonus for those seeking genuine connection and insider insights.

The Sum Up: Why This Tour Works

This private Chianti and San Gimignano tour offers a well-rounded taste of Tuscany’s best: stunning views, authentic towns, delicious food, and quality wines. It’s built for travelers who want an intimate experience with expert guides who share their love for the region.

The emphasis on organic farms, family-run wineries, and local traditions makes this tour stand out from generic group excursions. Plus, the flexibility and personalized attention ensure you’ll get a memorable day tailored to your interests.

Whether you’re a wine aficionado, a history enthusiast, or simply someone who wants to soak in the beauty of Tuscany with good company and great food, this tour is a solid choice. The combination of scenic drives, cultural stops, and a hearty Tuscan meal makes it an experience worth savoring.

FAQ

How long is the tour?
The tour lasts approximately 6 hours, starting at 9:00 am, including travel, sightseeing, and tasting stops.

Is transportation provided?
Yes, you’ll travel in an air-conditioned private vehicle with a professional driver, who also provides commentary on the scenery.

Can I customize the experience?
Since it’s a private tour, there’s room for personalized touches, though the itinerary is generally fixed to include San Gimignano, a farm visit, lunch, and wine tasting.

What is included in the price?
The fee covers private transportation, bottled water, a three-course Tuscan lunch, and five wine tastings, including olive oil.

Are there any additional costs?
Any extras outside the included activities—like souvenirs or additional tastings—are not included. You might find optional purchases at the farm or town.

Is the tour suitable for families?
Most travelers can participate, but it’s best for those comfortable with walking and sitting for periods. Check with the provider if you have specific needs.

How far in advance should I book?
On average, travelers book about 83 days ahead, indicating this is a popular experience.

What if I need to cancel?
You can cancel free of charge up to 24 hours before the tour, for a full refund.

This tour delivers a genuine, engaging taste of Tuscany, blending scenic beauty with culinary and cultural delights. If you’re looking for a personalized, authentic way to experience the region’s wine country, it’s hard to beat this carefully curated outing.