Wine tasting in TWO family wineries around Florence

If you’re considering a day out that combines the joys of wine, food, history, and stunning scenery, this Florence-based tour could be just what you need. Offering visits to two family-run wineries and stops in picturesque Tuscan villages, this experience promises a relaxed yet insightful taste of Italy’s most beloved wine region. With high praise from previous travelers and a focus on authentic family operations, it’s a chance to connect with Tuscany beyond the typical tourist trail.

What we love most about this tour is its personal touch—the owners and winemakers are involved in each visit, offering a rare glimpse into their craft and stories. Plus, the combination of scenic village stops and wine tastings makes it feel like an authentic Tuscan adventure. However, one thing to keep in mind is the group size—with a maximum of six travelers, the experience is intimate, but it requires booking well in advance. This tour suits those who appreciate small-group excursions, local wines, and charming villages rather than large, commercialized tastings.

Key Points

• Authentic Family Wineries: Visit two privately owned vineyards where owners personally guide tastings.
• Scenic Village Stops: Explore Montefioralle, Greve in Chianti, and a stunning 1400s villa with Italian gardens.
• Local Food Pairings: Enjoy delicious cheeses, cured meats, olive oil, and snacks paired with Chianti Classico.
• In-Depth Knowledge: Tour guides and winery owners share stories, process insights, and regional tips.
• Cultural Experience: Admire medieval architecture, panoramic countryside views, and traditional Tuscan charm.
• Value for Price: At $185.77, the experience offers a good balance of exclusivity, education, and delicious tasting.

An in-depth look at the tour experience

Starting Point and Logistics

The tour kicks off from Piazza dei Cavalleggeri in Florence, a convenient location near public transportation. The small group size, capped at six travelers, ensures a personalized experience, with the guide or driver often sharing insights on the way to the first stop. The tour lasts roughly five hours, making it a manageable yet enriching half-day escape from the city.

The tour operates every day from noon to 6 pm, giving flexibility for those who want a relaxed afternoon or to fit it into a broader Florence itinerary. When booking, most travelers plan about a month in advance, confirming the popularity and limited group size.

The First Stop: Montefioralle

Our journey begins in Montefioralle, a tiny, well-preserved medieval village that feels like stepping back in time. Here, a family-run winery welcomes us with open arms. The owners—who clearly treasure their heritage—lead us through their cellars, explaining their wine-making process and traditions.

This visit is not just about tasting wine but also about understanding the story behind each bottle. The owners take pride in their Chianti Classico, which is consistently praised for its quality. Alongside the wine, we sampled local cold cuts, cheeses, and extra virgin olive oil, all of which perfectly complement each sip.

Travelers rave about the cosy atmosphere and authenticity of this winery. One reviewer, Emilie, noted how the winery felt “very cosy” and the wine was “amazing.” The short stops in the village itself also provide excellent photo opportunities, with views of rolling hills and medieval stone walls.

Exploring Greve in Chianti

Next, we stopped in Greve, often considered the heart of Chianti. This bustling little town features a charming historic square surrounded by restaurants and bars. It’s a perfect spot for a quick stroll, some photos, or a coffee break. While only a brief stop of about 20 minutes, it offers a taste of local life and the chance to soak in the lively ambiance.

The Grand Finale: San Casciano in Val di Pesa

Our day culminates at a spectacular 1400s villa in San Casciano. The villa exudes fairy-tale charm with its Italian garden, cloistered courtyards, and stunning architecture. Here, we enjoyed a more intimate tasting experience with curated cured meats, cheeses, and olive oil, all paired with Chianti Classico.

The owner, a multi-generational winemaker, shared stories of family traditions and the secrets to their award-winning wines. Visitors have described this as a “wonderful experience” and a highlight of their trip, especially thanks to the beautiful setting and the personal stories shared during the tasting. It’s an ideal spot to relax, take photos, and savor the flavors of Tuscany.

Additional Details and Practical Tips

• Comfortable shoes are recommended, as walking through villages and the villa estate involves uneven terrain.
• The transportation between stops is by private vehicle or van, ensuring comfort and convenience.
• The price of $185.77 per person includes all tastings, snacks, and guided visits—making it a solid value considering the personalized nature of the experience.
• Be aware that most reviews highlight the knowledgeable guides and warm, welcoming wineries as key highlights, making the experience feel authentic rather than commercialized.
• The small group size means fewer crowds, more interaction, and tailored attention, which many travelers appreciate.

Authentic Experiences and Customer Feedback

Multiple reviewers have expressed how knowledgeable and friendly their guides and hosts were. Romana, our guide, was praised for her easy-going demeanor and wealth of regional knowledge. She was not just a driver but a storyteller, enhancing the experience with insights about Chianti wines, local culture, and hidden gems.

Guests also loved the chance to try several different wines—typically 4-5 at each winery—along with delicious local snacks. The atmosphere at these family wineries is described as “cosy,” “authentic,” and “more like visiting friends than a commercial tour.”

One traveler, Heidi, recounted how sitting privately with a fourth-generation winemaker in the middle of his vineyard was “more than we had hoped for,” and many reviews mention the special feeling of connecting with family-owned operations.

The Verdict on Value

For just under $200, this tour offers a personalized, educational, and delicious insight into the Chianti region’s wines and culture. It’s clear that the focus on small-scale, family-run wineries ensures high-quality experiences and authentic stories that larger tours might not offer.

Who will love this tour?

This experience is ideal for wine enthusiasts eager to learn about Chianti wines directly from passionate family owners. It’s perfect for travelers who enjoy scenic village strolls, authentic local food, and intimate encounters with locals. If you prefer larger groups or more commercialized tasting rooms, this might not be the best fit.

It’s best suited for those seeking a relaxed, authentic day out, with the flexibility to enjoy stunning views, delicious food, and heartfelt stories. The tour’s emphasis on local traditions and family heritage makes it a memorable highlight for anyone wanting to truly experience Tuscany’s soul.

Frequently Asked Questions

Is transportation included in the tour?
Yes, transportation between stops is provided, ensuring a comfortable journey through the Tuscan countryside.

What is the group size?
The tour limits to a maximum of six travelers for a more intimate experience.

Are there any age restrictions?
Most travelers can participate, and the experience is suitable for those who enjoy tasting and cultural visits. Comfortable shoes are recommended for walking.

How long is the tour?
It lasts approximately five hours, covering visits to three locations and tasting sessions.

What’s included in the price?
All wine tastings, food pairings (cheese, meats, olive oil), and guided visits are included in the $185.77 fee.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours in advance, with full refunds.

Is this tour suitable for vegetarians or non-drinkers?
While the focus is on wine and traditional Tuscan foods, specific dietary restrictions aren’t mentioned. Non-drinkers can enjoy the food and scenery.

What makes this tour stand out?
The personal involvement of winery owners, scenic villages, and authentic family-run wineries rather than commercial operations.

Final thoughts

This wine tasting tour around Florence offers a wonderful blend of authenticity, scenery, and education. You’ll get to meet passionate family owners, taste well-made Chianti Classico, and explore some of Tuscany’s most charming villages—all in a small, relaxed group. It’s a perfect choice for wine lovers, foodies, or anyone seeking a genuine cultural experience outside the crowded city.

The experience’s value lies in its personalized approach and attention to detail, making it more than just a tasting; it’s an immersion into Tuscany’s heart. Whether you want a romantic escape, a foodie adventure, or a memorable family activity, this tour checks all those boxes—and then some.

If you’re looking to connect with local traditions, enjoy spectacular views, and indulge in fantastic wines and foods, this tour will leave you with lasting memories. It’s a carefully curated experience that celebrates the best of Tuscany’s family wineries and scenic villages—authentic, intimate, and truly special.