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Discover Tuscany’s best with this small-group Vernaccia di San Gimignano wine tour from Florence, featuring historic wineries, a medieval town visit, and authentic tastings.
Tucked into the rolling hills of Tuscany, this small-group wine tour from Florence offers a well-rounded taste of the region’s celebrated wine culture. Spanning roughly seven hours, the experience combines visits to historic wineries, a charming medieval town, and a delicious Tuscan lunch—all with the intimacy of a group limited to just eight people. It’s a thoughtfully curated journey for those eager to explore Tuscany’s wine heritage without the hassle of navigating on your own or dealing with large tour crowds.
What we really appreciate about this tour is its blend of comfort, authenticity, and expert guidance. You’ll travel in a climate-controlled minivan, ensuring you stay comfortable regardless of the weather, and the small size means you get personalized attention from your guide. Plus, visiting private wineries like San Michele a Torri and a cozy family-run vineyard at Cappella Sant’Andrea offers a more genuine insight into local wine-making traditions.
That said, one thing to keep in mind is that this tour is best suited for those who enjoy a leisurely pace, good conversation, and a fair amount of wine tasting—so it’s not ideal if you’re looking for a quick, no-fuss overview. Also, since it departs at 9:30 am from Florence, early risers should be prepared for an active day. It’s perfect for wine lovers, history enthusiasts, and anyone wanting a taste of Tuscany’s wine-making soul without the overwhelming crowds.

The adventure begins at the meeting point in Florence, Piazza dei Cavalleggeri. From there, you’ll hop into a climate-controlled minivan—a thoughtful detail that keeps the journey comfortable amid Tuscany’s sometimes unpredictable weather. The drive to the first winery, San Michele a Torri, takes about an hour, giving you a scenic preview of Tuscany’s lush landscapes.
Travel in a small group (maximum 8 travelers) really makes a difference. It’s easier to chat, ask questions, and get tailored insights from your guide. The compact vehicle also means fewer stops and quicker transitions between sites, which helps maximize your time at each location.
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Your first stop is San Michele a Torri, one of the oldest wineries in Chianti. Here, you’ll find a family history dating back generations, making it one of the region’s most authentic stops. The winery produces Chianti Classico Riserva and Supertuscan Murtas, both highly regarded for their quality and expression of Tuscan terroir.
The three-hour visit involves a gentle walk through the vineyards and cellars, complemented by a wine tasting of their most esteemed bottles. You’ll also enjoy some traditional Italian snacks, which are perfect for pairing with the wines. The guides here are praised for their depth of knowledge—one reviewer called Andrea “amazing,” citing how much they learned about wine-making and Tuscany’s history in just a few hours.
What makes San Michele a Torri special: its long-standing tradition and the chance to taste wines crafted with care and respect for tradition. For those interested in the nuances of Chianti, this stop offers an authentic glimpse into the region’s winemaking roots.

Next, a short drive takes you to San Gimignano, the medieval town famous for its skyline of towers and preserved architecture. You’ll have about an hour here—ample time for a quick stroll through the Piazza della Cistena, browsing local shops, and maybe grabbing a gelato (which visitors rave about).
This free exploration lets you soak in the atmospheric streets, take photos of the iconic towers, and perhaps buy some souvenirs. Reviewers mention that the town’s charm is infectious, making it a highlight of the tour. It’s the perfect interlude to the wine-heavy morning, offering a chance to walk off the tasting buzz and marvel at Tuscany’s historic beauty.

The afternoon is dedicated to Cappella Sant’Andrea, a small, family-run winery operated by a young couple of vintners. This is where you’ll sit down to a two-course Tuscan lunch—a highlight for many. The setting is cozy, and the hosts are praised for their warmth and passion.
Along With the delicious meal, you’ll taste Vernaccia di San Gimignano, a white wine with a long tradition in the region. The guide will walk you through its unique characteristics, explaining how climate and soil influence its crisp, refreshing profile. This part of the tour is particularly valued for its personal touch—more intimate than a large tasting room, offering a genuine, heartfelt experience.
One reviewer mentioned that the “entire group learned a ton about wine and each other,” emphasizing how the guides foster a welcoming environment. The lunch and tasting together create a relaxed, convivial atmosphere, perfect for wine enthusiasts eager to deepen their understanding.

After this hearty lunch and wine tasting, you’ll head back to Florence. The return drive, about an hour, leaves plenty of time for reflection on the day’s discoveries. Many travelers appreciate how smoothly everything runs—nothing feels rushed, yet you get a comprehensive snapshot of Tuscany’s wine and culture.

The tour costs around $328.43 per person, which covers transportation, tastings, lunch, and snacks. Considering the inclusiveness and the small-group setting, it offers good value—special wineries, expert guides, and a personalized experience all bundled into one day.
Booking well in advance (average 181 days ahead) is recommended, especially in peak seasons. The tour’s maximum of 8 travelers keeps it intimate but also means spots fill up fast.
For those with dietary restrictions, vegetarian options are available—just be sure to specify when booking. And while hotel pickup isn’t included, the meeting point in Florence is centrally located and accessible by public transport.
This experience is ideal for wine lovers seeking an authentic, relaxed introduction to Tuscany’s vineyards. It’s perfect for travelers who enjoy small-group settings, want to learn from passionate guides, and appreciate visiting both historic and family-run wineries. The combination of scenic town exploration, delicious food, and quality wines makes it a well-rounded cultural experience.
It’s best suited to those comfortable with a full day of activity and tasting—moderate physical activity during brief walks and plenty of opportunities to indulge. If you’re traveling solo, couples, or small groups, you’ll find the limited size enhances the connection with guides and fellow travelers.
This small-group Vernaccia di San Gimignano wine tour offers a carefully curated look into Tuscany’s winemaking traditions, paired with stunning scenery and historic towns. The combination of expert guides, intimate visits, and a relaxed pace makes it a standout choice for those wanting to blend education, culture, and leisure.
You’ll love the way this tour balances tasting with storytelling, giving you insights into both white and red wines that you’re unlikely to get on larger, more impersonal tours. The visit to local wineries deepens the connection to the land and its people, adding a layer of authenticity that’s often missing elsewhere.
Whether you’re a seasoned oenophile or a curious newcomer, this experience delivers a memorable taste of Tuscany—its landscapes, its history, and its wines—all in one delightful day.
Is the tour suitable for vegetarians? Yes, vegetarian options are available, and you should advise at booking.
How long does the tour last? The entire experience is approximately 7 hours, starting at 9:30 am and ending back in Florence.
What is included in the price? The tour includes guide services, local taxes, transportation, wine tastings, alcoholic beverages, a two-course lunch, and snacks.
Are there any age restrictions? Yes, the minimum age is 18 years, as the tour involves wine tastings.
What should I wear? Comfortable clothing suitable for walking and dining. Bring a hat or sunglasses if sunny, and perhaps a light jacket for the evenings.
Can I cancel if my plans change? Yes, free cancellation is available up to 24 hours before the tour, with a full refund.
This thoughtfully designed wine tour provides a balanced introduction to Tuscany’s vinicultural treasures, perfect for those seeking an authentic, intimate, and enjoyable experience.