Wine tasting in TWO family wineries around Florence

Discover the Charm of Tuscany: Wine Tasting at Two Family Wineries Near Florence

Imagine yourself sipping exceptional Chianti Classico in the company of passionate local owners, with breathtaking views of the Tuscan countryside spreading out behind them. This 5-hour guided tour offers a perfect blend of authentic winery visits, charming villages, and cultural insights—an experience that highlights the genuine warmth and flavor of the region. Priced at around $185.77 per person, it’s a well-balanced investment for anyone eager to explore the heart of Italy’s wine country without the crowds or commercialized feel.

What we love about this tour is how personal it feels—you’re not just a tourist, but a guest in a family’s home, hearing stories about winemaking passed down through generations. Plus, the stops at Montefioralle and San Casciano in Pesa offer picturesque scenes and quaint streets that make for perfect photo ops.

A small consideration is the group size, limited to just six travelers, which is fantastic for intimacy but requires early booking—on average, travelers plan about a month in advance. If you’re seeking a relaxed, authentic experience with knowledgeable guides and lots of opportunities for tasting and picture-taking, this tour fits the bill. It’s especially suited for those who appreciate local food, beautiful scenery, and genuine family-run wineries.

Key Points

• Authentic family wineries offer a personal touch and stories behind each bottle.
• Beautiful stops at Montefioralle and San Casciano provide scenic views and photo-worthy moments.
• Expert guidance enhances your understanding of Chianti wines and local traditions.
• Tastings include Chianti Classico, cheeses, cured meats, and olive oil, with delicious snacks.
• Small group size (max 6) ensures a personalized, relaxed experience.
• Flexible schedule with pickup included, running daily from noon to late afternoon.

An In-Depth Look at the Tuscany Wine Tasting Tour

The Itinerary and What It Means for You

The journey begins in Piazza dei Cavalleggeri in Florence, where your small group will meet and start the adventure. The tour is about five hours long, giving plenty of time to savor each part of the day without feeling rushed. The limited group size (up to six people) means you’ll get personalized attention and an intimate atmosphere—crucial when tasting wines and exploring family-run wineries.

First Stop: Montefioralle
This medieval village feels like stepping back in time. The visit to a local family winery here is the highlight for many. You’ll get to taste Chianti Classico, paired with cold cuts, cheeses, and extra virgin olive oil. The owner will share stories about their winemaking tradition, adding context to each sip. The reviews praise how cozy and genuine these wineries feel—more like visiting friends than a tourist trap.

During this stop, you’ll also enjoy sweeping views of the Tuscan countryside. Photographers will appreciate the chance to snap shots of the idyllic landscape and ancient stone streets. This stop lasts around two hours, giving you ample time to absorb the scenery and learn about the local products.

Second Stop: Greve in Chianti
A brief 20-minute visit, Greve is the bustling heart of Chianti’s wine country, famous for its picturesque small square surrounded by shops and cafes. You might find this stop perfect for a quick stroll or a coffee break, with some time to soak in the lively atmosphere. It’s the ideal place for a quick immersion into local life.

Third Stop: San Casciano in Pesa
This 1400s villa seems straight out of a fairy tale, with a stunning Italian garden and a more luxurious setting. Here, you’ll enjoy another round of wine tastings—including Chianti Classico—paired with cured meats, cheeses, and olive oil. The owner, often a descendant of the original family, will share history and insights, making each sip meaningful. It’s a fantastic way to understand the deep roots of Tuscan winemaking, and reviews mention how romantic and special this setting feels.

What Sets This Tour Apart?

What truly stands out is the knowledge and friendliness of the guides, with reviewers consistently praising Romana and others for their helpfulness and expertise. As Emilie notes, Romana’s suggestions for local restaurants added extra value to the experience. You’ll learn about Chianti’s wine varieties, local food traditions, and the significance of family-owned wineries, which are often overlooked by larger, commercial operations.

The tastings are not rushed; expect to try 4-5 different wines each time, accompanied by delicious snacks. Several reviewers, including Patty and Elin, highlight how much they learned about the region’s wines, making the experience both fun and educational.

What About the Cost?

At just under $190 per person, the tour offers a lot of value. The inclusion of guided visits, tastings, and the chance to wander charming villages would easily cost more if booked separately. The small group size ensures you aren’t just another face in the crowd, and the personalized experience makes it worth the price for wine lovers.

Practical Details and Tips

• Pickup is included, meeting at Piazza dei Cavalleggeri—conveniently located in Florence and accessible via public transportation.
• Wear comfortable shoes, as you’ll be walking through villages and possibly on uneven surfaces.
• Booking is recommended about 32 days in advance—these small-group tours fill quickly.
• The tour runs daily from 12 PM to 6 PM, fitting nicely into a relaxed afternoon plan.

Who Will Love This Tour?

If you’re passionate about authentic wine experiences and enjoy exploring small villages away from tourist hotspots, this tour is perfect. It’s especially great if you appreciate family-run wineries and want to learn directly from the owners, as many reviews emphasize the warm, personal stories shared. It also suits travelers looking for a relaxed pace and beautiful scenery, with plenty of opportunities for photos and tasting.

Those with a taste for local cuisine, including cheeses and cured meats, will find this experience particularly satisfying. It’s ideal for couples, small groups of friends, or anyone eager to deepen their understanding of Chianti’s wines and traditions without spending a fortune.

Frequently Asked Questions

Is the tour suitable for all ages?
Yes, most travelers can participate, but it’s best suited for adults who enjoy wine tasting and walking through villages.

How long does each stop last?
The visit to Montefioralle lasts about two hours; Greve is a quick 20-minute stop, and San Casciano takes around two hours, giving a relaxed overall pace.

Are there any dietary restrictions accommodated?
While specific accommodations aren’t mentioned, the focus on local foods such as cheeses, cured meats, and olive oil suggests a traditional Tuscan fare.

Is transportation included?
Yes, pickup is offered from Florence’s Piazza dei Cavalleggeri, making travel arrangements hassle-free.

What should I wear?
Comfortable shoes are recommended, especially since you’ll be walking through villages and outdoor areas.

Can I cancel if my plans change?
Yes, there’s free cancellation up to 24 hours before the tour, offering flexibility if needed.

Final Thoughts

This wine tasting tour around Florence offers a genuine taste of Tuscany’s heritage—visiting family-owned wineries with stories as rich as their wines. The blend of beautiful scenery, expert guides, and delicious tastings makes it a standout choice for those wanting an authentic, relaxed day in the countryside.

It’s especially suited for travelers who value small-group intimacy, local flavor, and the chance to sample outstanding Chianti in a setting that feels like visiting friends’ homes. If you’re after more than just a quick wine tasting, but rather a meaningful connection to Tuscan traditions, this tour is well worth considering.

In essence, this experience offers a genuine slice of Tuscany—beautiful villages, heartfelt family stories, and some of Italy’s finest wines—all tailored for those eager to explore beyond the tourist trail. It’s a memorable, authentic journey into the soul of Chianti wine country.