Wine tasting in TWO family wineries around Florence

If you’re dreaming of combining your love for Italy’s iconic landscapes with some serious wine tasting, this wine tour in two family-run wineries around Florence could be just what you need. It’s a carefully curated experience that promises not just to quench your thirst for good wine but also to give you a taste of authentic Tuscan life. We’ve looked into what makes this tour stand out—and what you might want to consider before booking.

Two things that really caught our eye are the personal touch of family-owned wineries and the chance to explore charming, less commercialized spots in Tuscany like Montefioralle and San Casciano. The guides and owners are said to be knowledgeable and friendly, making the experience feel more like a visit to friends’ homes rather than a commercial operation. The second perk is the scenic stops—imagine wandering through medieval villages and soaking in panoramic views of rolling vineyards and olive groves.

A potential downside? The tour lasts about five hours, which might be a bit long if you prefer more relaxed, leisurely mornings or if you’re not used to group activities. It’s also a small-group experience with a maximum of six travelers, which is great for intimacy but could be less flexible or lively if you prefer larger groups. Still, for those who love a personalized feel and detailed attention, this is a solid pick.

This experience suits travelers who appreciate genuine local flavors, stunning vistas, and a deep dive into Chianti’s wine culture without the crowds. Perfect for couples, small groups, or anyone eager to taste into Tuscany’s soul while enjoying a structured, guided day.

Key Points

• Authentic Family Wineries: Visits to small, family-run farms where you’ll taste wines made with love.
• Scenic Villages: Stops at Montefioralle and San Casciano offer charming, historic sights and photo ops.
• Expert Guides: The owners and guides are praised for their knowledge and friendliness, adding a personal touch.
• Tasty Pairings: Expect tastings of Chianti Classico accompanied by local cold cuts, cheeses, and olive oil.
• Beautiful Landscapes: Expect panoramic views of the Tuscan countryside, perfect for photo lovers.
• Flexible Timing: Tours run daily and can be booked well in advance, with a pickup option included.

The Experience in Detail

Starting Point and Overall Structure

The tour kicks off at Piazza dei Cavalleggeri in Florence, a convenient location near public transport. From there, you’ll head out with a small group—usually no more than six people—to explore some of Tuscany’s most treasured spots. The day lasts about five hours, giving you enough time to enjoy the visits without feeling rushed, though it’s still a fairly full schedule.

Visiting Montefioralle and the Family Winery

Your first stop is Montefioralle, a tiny, medieval jewel that’s less touristy than other hilltop villages. Here, you’ll step into a family-owned winery where the owner will guide you through their cellars and share stories about their farming traditions. What makes this visit compelling is the chance to taste Chianti Classico alongside local cold cuts, cheeses, and extra virgin olive oil. The wines are described as excellent, and the cozy setting makes you feel like part of the family.

One of the reviews highlights, “Romana was so helpful and easy-going,” emphasizing that the guide’s friendliness enhances the experience. It’s not just about drinking wine but understanding the passion behind each bottle and the story of the farm.

Exploring Greve in Chianti

Next, you’ll stop in Greve, a picturesque town with a small, historic square surrounded by cafes and restaurants. This brief 20-minute visit might be a quick photo opportunity or a chance to stretch your legs. It’s a typical Chianti town, so expect to see local shops and a relaxed vibe that perfectly embodies the region.

The Villa in San Casciano in Val di Pesa

The highlight for many seems to be the visit to a 1400s villa in San Casciano, a place that looks straight out of a fairy tale. The villa boasts an Italian garden and a tranquil atmosphere. Here, you’ll indulge in another round of tastings similar to the first, pairing Chianti with cured meats, cheeses, and olive oil. The owner will likely tell stories about the estate’s history, adding depth to your tasting experience.

One reviewer describes it as “a thousand and one nights,” which perfectly captures the romantic, timeless feel of this spot. Expect to admire spectacular views of the Tuscan countryside while sampling some of the region’s finest products.

The Wines and Food

Throughout the tour, you’ll enjoy 4-5 different wines at the wineries, with plenty of opportunities to savor the nuances of Chianti Classico. The tastings are complemented by local snacks and tapas-style plates, which help balance the wine’s tannins and enhance flavors. Many guests mention the deliciousness of the food along with the wines, making this not just a tasting but a full sensory experience.

Extra Details

The tour is designed to be informative and personal, with the owners explaining their craft and the region’s terroir. Reviewers consistently mention the knowledgeable guides who make the experience engaging and relaxed. For example, one quote notes how Romana “knew a lot about the neighborhoods and wine,” which really helps you appreciate the nuances of Chianti wines.

Practicalities

The entire experience is costing about $185.77 per person, which for the quality of the visits, tastings, and personalized attention, seems fair. The tour is available daily, and the booking window extends well into 2026, giving you flexibility. Comfortable shoes are recommended since there’s some walking, especially around the villages and the villa gardens.

The tour includes pickup, which adds to its convenience, especially if you’re coming from Florence. And with a free cancellation policy up to 24 hours in advance, you can plan without too much worry.

Who Will Love This Tour?

If you’re after a small-group, intimate experience that combines great wines with scenic stops and authentic Tuscan hospitality, this tour is one to consider. It’s especially well-suited for those who want to learn more about Chianti wines from passionate family producers—without the commercial touristic feel.

The multiple reviews praising knowledgeable guides and delicious pairings suggest that food and wine enthusiasts will find plenty to enjoy. Also, if picturesque villages and historic villas are your thing, you’ll find plenty of photo-worthy moments here. This isn’t a wild party or a large bus tour; it’s about quality, depth, and a relaxed pace.

This experience might not be the best choice if you’re looking for a very casual or quick tasting, or if you prefer larger groups for a livelier atmosphere. But for those who value personal stories, authentic flavors, and charming scenery, this will hit the spot.

FAQs

How long does the tour last?
The tour lasts approximately five hours, including visits to two wineries, stops in villages, and tasting sessions.

Is transportation included?
Yes, there is a pickup offered from a meeting point in Florence, making it easy to start the day without worrying about parking or navigation.

What is the group size?
The tour is limited to a maximum of six travelers, ensuring a personalized experience.

What should I wear?
Comfortable shoes are recommended since there will be some walking around villages and the villas.

Can I cancel this tour?
Yes, there is a free cancellation policy if you cancel at least 24 hours before the scheduled start.

Are children allowed?
While not specifically mentioned, the relaxed, adult-focused nature of the tour suggests it’s best suited for guests of legal drinking age, especially given the wine tastings.

Is the tour suitable for people with mobility issues?
The tour involves walking through villages and gardens, so those with mobility concerns should consider this.

How many wines will I taste?
You’ll likely sample 4-5 different wines during the visits, paired with local snacks.

What makes this tour different from others?
The focus on family wineries and the opportunity to meet owners who are passionate about their craft set this experience apart from more commercialized tours.

Is the price justified?
Given the intimate setting, personalized attention, and quality tastings, most reviews find the cost reasonable, especially considering the scenic stops and local food included.

Final Thoughts

If you’re looking for a genuine slice of Tuscany that offers more than just pretty views, this wine tasting tour is a real winner. It combines the pleasures of expertly made Chianti with the charm of small villages, all delivered through guides and owners who love sharing their passion. The experience feels authentic, relaxed, and deeply connected to local traditions—ideal if you want to learn, taste, and enjoy without the crowds.

This tour is best suited for couples, small groups, or anyone eager to get a real feel for Tuscany’s wine culture in an intimate setting. It’s a great choice if you value quality over quantity, and if you’re happy to spend a few hours immersed in beautiful scenery, delicious food, and exceptional wine. Just remember, it’s a full, engaging day, so plan to come prepared for a bit of walking and a lot of tasting.

Whether you’re a seasoned wine lover or simply curious about Tuscany’s rich winemaking tradition, this experience will leave you with memorable sights, flavors, and stories to take home.