Wine tasting in TWO family wineries around Florence

Exploring Tuscany’s Winemaking Heritage: A Deep Dive into the Florence Family Wineries Tour

The allure of Tuscany isn’t just in its landscapes, but also in its centuries-old winemaking traditions. This wine tasting experience around Florence offers a chance to visit two family-run wineries, explore picturesque villages, and savor some of Italy’s best Chianti Classico wines. It’s a well-crafted tour that combines history, stunning scenery, and authentic flavors — all in about five hours.

What really stands out for us is the personal touch: every visit is guided by the winery owners themselves, who are passionate about sharing their stories and products. It’s also a fantastic value, considering the quality of the wines, the variety of tastings, and the memorable stops included.

Of course, with any tour, there are a few things to consider. The group size is small (maximum six travelers), which means a more intimate experience, but it also requires booking well in advance—on average about a month ahead. For those who enjoy personalized attention, relaxed pacing, and a taste of genuine Tuscan hospitality, this tour ticks many boxes.

This experience suits wine lovers eager for insight into Tuscany’s vineyards, travelers who appreciate charming villages, and anyone wanting to combine scenic sightseeing with delicious tastings. Whether you’re celebrating a special occasion or just want a memorable day out from Florence, it’s a well-rounded choice.

Key Points

• Authentic Family Wineries: Visits are hosted by the actual owners, sharing personal stories and craftsmanship.
• Stunning Villages & Scenic Views: Stops include Montefioralle and San Casciano in Val di Pesa, both picture-perfect medieval towns.
• Tasting & Food Pairings: Enjoy Chianti Classico alongside local cheeses, cured meats, and extra virgin olive oil.
• Small Group Experience: Max six travelers for a more relaxed, personalized feel.
• Expert Guides: Knowledgeable hosts like Romana add depth and fun to the day.
• Flexible, Convenient: Pickup from Florence and a mobile ticket make logistics easier.

A Detailed Look at the Tour Itinerary

Meeting Point & Transportation

The tour begins at Piazza dei Cavalleggeri in Florence, a central location accessible by public transport. Once everyone is gathered, you’ll be chauffeured in a comfortable vehicle that fits the small group, ensuring a cozy and intimate atmosphere. The timing—starting around midday—allows for a relaxed exploration of the Tuscan countryside without feeling rushed.

Montefioralle: The Medieval Charm & First Winery

The first stop is the enchanting village of Montefioralle, renowned as one of Italy’s most beautiful medieval towns. Here, you visit a family-owned winery where the owners warmly welcome you into their cellar. While touring the vineyard and cellars, expect to learn about their production process and family history, which adds meaningful context to the tastings.

You’ll sample Chianti Classico alongside local cold cuts, cheeses, and extra virgin olive oil. Reviewers like Emilie praise the cosy ambiance of these family wineries, describing the wines as “amazing” and emphasizing the helpfulness of guides like Romana. The views of rolling hills and vineyards from the village are spectacular, making it ideal for short photo stops.

Greve in Chianti: The Heart of Winemaking

Next, the tour pauses in Greve in Chianti, a charming small town with a bustling square surrounded by cafes and shops. This 20-minute stop isn’t long but gives you a quick taste of local life and the chance to stretch your legs. It’s a good opportunity to browse or grab a quick coffee before heading to the next, more exclusive part of the tour.

San Casciano in Val di Pesa: A Villa & More Tasting

The final stop is at a beautiful 1400s villa with a stunning Italian garden, reminiscent of stories from a thousand and one nights. Here, you’ll experience a second family-run winery, where the owner will guide you through more tastings, including 4-5 different wines, paired with cured meats, cheeses, and olive oil.

Reviewers like ElinH mention that the tastings were beyond good, and Romana’s insights made the experience even richer. Many note the relaxed yet informative atmosphere—a perfect setting for wine enthusiasts to deepen their understanding of Chianti wines and Tuscan food.

End of Tour & Return to Florence

The tour wraps up back at the starting point, allowing travelers to continue exploring Florence or relax after a full day of sensory delights. The timing ensures you’re back in the city by late afternoon, with plenty of time to enjoy dinner or more sightseeing.

The Value of This Wine Tasting Tour

When considering the cost of approximately $185.77 per person, the value lies in the combination of personal guidance, authentic family wineries, and scenic stops. The small group size ensures a more personal and flexible experience, allowing guides like Romana to tailor insights and answer questions in-depth.

The tastings are thoughtfully curated, with local produce and wines praised for their quality, making this experience ideal for those who want more than just a standard wine tasting. The inclusion of regional specialties like cold cuts and olive oil enhances the authenticity and makes each stop feel like a mini feast.

On top of that, the tour’s scheduled hours—12 PM to 6 PM—strike a nice balance, offering a relaxed pace without feeling rushed. The convenience of pickup and mobile tickets simplifies logistics, especially for travelers staying in Florence.

Why This Tour Excels According to Reviews

• Knowledgeable Hosts: Romana and other guides are commended for their friendly, insightful commentary.
• Beautiful Settings: The medieval villages and villa gardens are described as picturesque and breathtaking.
• Quality of Wines & Food: Reviewers highlight the excellent wines and delicious snacks, praising the variety and authenticity.
• Small Group Comfort: The limited size makes it feel exclusive and allows for personalized interaction.

Who Should Book This Experience?

This tour is perfect for wine enthusiasts interested in learning about Chianti wines from genuine family producers. It’s also an excellent choice for scenery lovers who enjoy exploring charming villages and historic towns.

If you prefer small, intimate groups over large bus tours, and want to combine wine tasting with a bit of sightseeing, this experience delivers. It’s suited for travelers with moderate mobility, as comfortable shoes are recommended, especially given the cobbled streets and villa gardens.

However, if you’re a solo traveler or part of a small group eager for genuine, hands-on experiences with expert hosts, you’ll find this tour particularly rewarding. Those seeking a highly curated, relaxed, and authentic taste of Tuscany’s winemaking culture will feel right at home here.

Frequently Asked Questions

Is transportation provided?
Yes, pickup is offered from a designated meeting point in Florence, making logistics easy. The journey to the wineries is in a comfortable vehicle.

What is the tour duration?
The entire experience lasts approximately 5 hours, from noon to around 6 pm, including all stops and tastings.

How many people are in each group?
The tour is limited to a maximum of 6 travelers, ensuring a more personalized experience.

What is included in the tasting?
You will taste multiple Chianti Classico wines at each winery, paired with regional snacks such as cured meats, cheeses, and extra virgin olive oil.

Are the visits suitable for children or non-drinkers?
While the focus is on wine tasting, non-drinkers can enjoy the scenic villages, food, and the gardens at Villa San Casciano.

Is the tour suitable for all ages?
Most travelers can participate; comfortable shoes are recommended for walking through villages and gardens.

Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the scheduled start, with a full refund.

How far in advance should I book?
On average, this tour is booked about 32 days ahead, so early reservation is recommended, especially during peak seasons.

What should I wear?
Comfortable shoes are advisable given the cobblestone streets and garden walks.

Final Thoughts

This wine tasting tour around Florence offers a genuine glimpse into Tuscany’s winemaking roots through visits to two family-operated vineyards. The small, intimate setting, guided by passionate hosts, ensures a memorable experience that’s both educational and delicious. Expect beautiful views, authentic regional foods, and wines that are truly representative of Chianti’s best.

Perfect for wine lovers, curious travelers, or anyone seeking a relaxed day out immersed in Italy’s countryside charm, this tour balances scenic beauty, cultural richness, and flavorful indulgence in an approachable, well-organized package.

If you’re after a more personal, off-the-beaten-path experience that combines history, scenery, and superb wine, this tour is well worth the investment. Just remember to book in advance—these cozy wineries fill up quickly!