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Discover the charm of Tuscany with a San Gimignano wine tasting tour, featuring authentic Chianti wines, a delicious local lunch, and a cellar visit.

If you’re heading to Tuscany and want to indulge in some of the region’s finest wines paired with traditional dishes, the San Gimignano Chianti wine tasting and lunch tour offers a delightful peek into local craftsmanship and culinary heritage. This experience, run by Hidden Experiences, emphasizes intimacy and authenticity, making it ideal for those who prefer personalized tours over large group excursions. It’s a chance to step just outside San Gimignano’s medieval walls and into a family-run winery where stories and wines flow freely.
What truly catches the eye about this tour is the small group size, which allows for a relaxed and engaging atmosphere. Coupled with a knowledgeable host, you’ll get more than just a tasting—you’ll learn about the history, the organic winemaking process started by the owner’s grandfather, and how Tuscan flavors are perfectly paired with local wines. The only downside? The tour lasts about two hours, so if you’re craving a longer, more in-depth excursion, this might feel a tad brief.
This experience is best suited for wine lovers, foodies, and travelers seeking a genuine, intimate connection with Tuscany’s wine culture. It’s perfect if you appreciate a mix of education and tasting in a cozy setting, with plenty of tasty bites to complement the wines.
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The tour begins at Fontaleoni, Loc. Santa Maria Fonte Leone, a peaceful spot a few steps from the historic heart of San Gimignano. Arriving at 12:00 pm, you’ll be greeted by your guide, Simona, whose personal touch is a highlight—she’s the granddaughter of the winery’s founder and clearly takes pride in sharing her family’s history and organic wine practices.
One of the standout moments is the tour of the cellar and vineyards. Unlike large commercial wineries, this family-run operation keeps things personal. You’ll see where the wine is stored and learn about their organic practices, which Simona emphasizes are rooted in tradition and family values. You’ll also hear about the history of the winery, started by her grandfather, adding an emotional layer to your tasting.
This visit offers more than just tasting palate-pleasing wines; it’s an educational walk through the process of how organic, traditional wines are made, emphasizing Tuscan pride in terroir and craftsmanship.
Following the cellar tour, the real fun begins with sampling five wines. These are paired with a selection of typical Tuscan products—think cured meats, cheeses, and local bread—highlighting how food and wine are inseparable in Italian culture.
The tasting includes Cantucci and Vinsanto, a classic Tuscan pairing, with some reviewers noting that this sweet ending is a perfect complement to the wine experience. You’ll also get to enjoy a grappa tasting, which adds a spirited kick and offers insight into another traditional Tuscan distillation.
Rachel, a recent guest, described the experience as “very personalized,” emphasizing how her host Simona made her feel like she was visiting family. Her highlight was the story behind the winery’s organic practices, passed down through generations, which adds a layer of authenticity to the wines.
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The lunch is more than just a snack; it’s an authentic Tuscan meal with first courses and local specialties. The focus on local products means you’ll taste the region’s best cured meats and cheeses, which complement the wines beautifully. The relaxed pace and small group size make it feel like a private gathering—perfect for wine aficionados or those craving genuine Tuscan hospitality.
At $80.99 per person, this tour offers excellent value, especially considering the personalized attention, the quality of the wines, and the culinary experience. You’re not just tasting; you’re learning, eating, and soaking in the scenic surroundings—all in about two hours. Plus, with free cancellation policy up to 24 hours before, it offers flexibility for your plans.
The tour’s limited group size (max 15) ensures you won’t feel lost in a crowd, and the mobile ticket makes it easy to organize your day.
This experience is ideal for wine lovers eager to learn about Tuscan traditions and foodies wanting to taste authentic local flavors. It’s also a good fit for those who enjoy small group, personalized tours over generic, large-scale offerings. If you’re interested in organic practices and family stories behind the wines, you’ll find this especially rewarding.
The San Gimignano Chianti wine tasting and lunch tour shines as an intimate, educational, and delicious way to spend a few hours outside the historic town walls. You get to explore a family-run winery, learn about traditional and organic winemaking, and enjoy a thoughtfully curated tasting paired with local delicacies. The small-group format ensures personal attention, making it feel more like a visit to a friend’s countryside home than a commercial tour.
For travelers who appreciate authentic experiences, high-quality wines, and genuine Tuscan hospitality, this tour offers excellent value and a memorable taste of Tuscany. It strikes a fine balance between education and indulgence, making it a standout choice for those wanting to deepen their connection with Italy’s wine culture.
Where does the tour start?
The tour begins at Fontaleoni, Loc. Santa Maria Fonte Leone, just outside San Gimignano.
What time does the tour start?
It starts at 12:00 pm, giving you a relaxed midday experience.
How long does the tour last?
Approximately two hours, including cellar visits, tastings, and lunch.
Is the tour suitable for children or non-drinkers?
While primarily focused on wine, the tour involves tasting multiple wines, so it’s best for adults. However, non-drinkers can still enjoy the food and the scenic vineyard visits.
Can I cancel if my plans change?
Yes, full cancellation is available up to 24 hours before the scheduled start, with a full refund.
How many people typically participate?
The tour is limited to a maximum of 15 travelers, ensuring a personal experience.
Are gratuities included?
Tips are not included, so you may choose to tip your guide if you feel it’s deserved.
What’s included in the price?
The fee covers five wine tastings, lunch with local products, grappa tasting, bottled water, and the cellar and vineyard visit.
Do I need to prepare anything special?
Just arrive on time, wear comfortable shoes, and come with an appetite for good wine and food.
Is the wine organic?
Yes, the owner’s family has been practicing organic winemaking since the winery’s inception, which is a core part of the experience.
Whether you’re a dedicated oenophile or simply someone curious about Tuscany’s wine traditions, this tour offers a delicious, authentic taste that’s hard to beat.