Florence: Hiking Tuscany & Chianti wine 3 wineries and lunch

Tuscany’s Hidden Gems: Hiking, Wineries, and Authentic Flavors

Our review covers an 8-hour tour through the heart of Chianti’s wine country, a journey that combines gentle hikes, visits to charming organic wineries, and a taste of true Tuscan hospitality. While we haven’t personally taken this tour, the glowing reviews and detailed itinerary paint a picture of a well-rounded experience perfect for wine lovers, nature enthusiasts, and curious travelers alike.

What makes this experience stand out? First, the emphasis on sustainable tourism and small group size offers a more intimate, authentic encounter with Italy’s renowned wine region. Second, the blend of nature walks, local food, and wine tastings creates a relaxed, all-encompassing day. Third, the focus on local, organic producers ensures you’re supporting genuine small businesses. The only thing to keep in mind is that the terrain involves about 8 km of walking on uneven paths, so it’s best suited for those comfortable with some light outdoor activity. This experience appeals most to travelers wanting a relaxed, authentic day out in Tuscany, away from crowded tourist spots.

You can check availability for your dates here:

Key Points

• Authentic small group experience limited to 7 people for a more personalized adventure.
• Eco-friendly focus supporting local organic/biodynamic wineries and producers.
• Scenic landscape with walking routes through vineyards, olive groves, and historic villages.
• Expert guides like Lorenzo and Stefano, known for their knowledge and flexibility.
• Culinary delights including a Tuscan lunch, olive oil, and cheese tastings.
• Balanced itinerary combining hiking, wine tasting, and cultural insights without feeling rushed.

Exploring Tuscany on Foot and in Style

This tour offers a wonderful way to explore Tuscany’s rolling hills and historic wineries without feeling like just another tourist. The experience begins with a pick-up in Florence, then a scenic drive along lesser-known roads, giving you a taste of Tuscany’s natural beauty even before you step out of the van. The tour’s small size—limited to 7 participants—means you’ll get more personalized attention, which is especially valuable when exploring family-run wineries and hearing stories directly from the producers.

The highlight is the hiking in the Chianti Classico region, starting at the Conca d’Oro, a natural amphitheater famous for producing some of the best Chianti wines. The gentle walk through vineyards and olive groves is designed to be accessible, offering about 8 km of paths suitable for many fitness levels. Reviewers like Kate appreciated the flexibility Lorenzo showed, compensating for weather with backup adventures and visits to small towns. This flexibility and personal touch seem to be a hallmark of this tour.

Visiting Historic, Family-Run Wineries

The first stop is a 12th-century family-owned winery, which gives visitors a real sense of history and tradition. The wine cellar, once used as a medieval post, offers an atmospheric setting for tasting the wines and local foods. Guests like Jane loved the chance to explore a location that has been in operation for centuries, making the tasting experience feel more meaningful.

From there, the walk continues through olive groves and vineyards toward the second winery. This second stop is run by a family with three generations of farming experience. Expect to sample up to 11 wines—a generous tasting that makes the price of this tour quite reasonable considering the quality and variety of wines, cheeses, and extra virgin olive oil included. Reviewers like Frances praise the guide’s passion and detailed explanations about the wine-making process, making each tasting not just a sip but a story.

Lunch here is a highlight. Usually, it’s served in the winery’s dining area, featuring Tuscan starters and pasta paired with local wines. Jessica described the lunch as “out of this world,” and it’s a perfect chance to relax and refuel for the walk to the last winery.

The Modern Art Winery with Stunning Views

The final stop is a contemporary winery perched at the top of the hills overlooking Montefioralle, an ancient castle town. This winery blends modern techniques with traditional knowledge, offering a different perspective on winemaking. The tasting here tends to be the last, allowing you to reflect on the day while enjoying panoramic views. This winery’s creative vibe complements the historical stops and offers a fresh, innovative contrast.

The guided tasting emphasizes the blending of old and new, with plenty of stories about how art, culture, and wine intertwine here. Guests have noted that this stop provides a fantastic finale to the day with a diverse selection of wines and a chance to take in the scenic horizon.

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Authentic Food and Olive Oil Experiences

Food is an integral part of this tour. Not only do you enjoy a hearty Tuscan lunch, but also extra virgin olive oil tastings and local delicacies like cheese, salami, and ham. One reviewer mentioned watching an olive harvest, giving a true sense of the region’s agricultural traditions. Saffron producer visits are sometimes included, adding another layer of local flavor.

These tastings are more than just palate-pleasers—they’re educational. Guides like Lorenzo and Stefano are praised for their expertise and storytelling, helping you connect with what makes Tuscan products so special. The emphasis on sustainable and organic practices also means you’re supporting small producers dedicated to quality and tradition.

Practical Details and Considerations

Pricing for this tour offers good value. It includes transportation in an air-conditioned minivan, all tastings, guided hikes, and a delicious Tuscan lunch. The small group size means fewer crowds, more engaging conversations, and better access to the wineries’ owners and workers. The tour lasts around 8 hours, with flexible starting times based on availability.

Participants should be prepared for rougher terrain—wear comfortable hiking shoes, bring sun protection, and stay hydrated. The walking is manageable, but uneven paths and some ups and downs mean it’s best suited for those comfortable on foot.

Note that hotel pickup and drop-off are not included, so you’ll need to organize your own transportation to the meeting point, located at Cafè Lietta in Florence. The tour takes place rain or shine, unless weather alerts are severe, so plan accordingly with appropriate clothing.

Authentic, Sustainable, and Personal

This experience is praised for its authenticity—visiting family-owned wineries, learning directly from passionate producers, and supporting sustainable local practices. Guests loved the knowledgeable guides—Lorenzo and Stefano—who made the day informative and fun, often sharing stories that bring the region’s history to life.

The delicious food, excellent wine selection, and scenic views are the core highlights, making it a memorable day for anyone craving a mix of outdoor activity, culture, and genuine hospitality. Reviewers emphasized this as a highlight of their trip, with Jessica calling it “the best day of the trip” thanks to the charming guides and relaxed pace.

Who Should Consider This Tour?

If you’re a wine enthusiast eager to learn about Chianti’s winemaking traditions in a small, intimate setting, this tour is a great pick. Nature lovers will appreciate the gentle hikes and stunning landscape views, while foodies will delight in the authentic Tuscan lunch and tastings.

It’s ideal for travelers who want to support sustainable tourism and small-scale producers, and for those seeking a relaxed, scenic day out away from busy tourist traps. The tour isn’t suited for pregnant women, people with mobility issues, or children under 18—mainly due to the walking involved.

FAQ

Is transportation included?
No, transportation to the meeting point isn’t included. The tour begins at Cafè Lietta in Florence, and you’ll be transported via air-conditioned minivan during the day.

What should I wear?
Comfortable clothes, hiking shoes, sun protection like sunscreen and a hat, and water are recommended. Weather-appropriate attire ensures you enjoy the walk and outdoor tastings comfortably.

How much walking is involved?
Expect around 8 km on uneven paths, with some ups and downs. The terrain is manageable but may be challenging for those with mobility impairments.

Are wine tastings unlimited?
You’ll taste approximately 11 wines across the three wineries, along with olive oil, cheese, and other local products, making it a generous tasting experience.

Can I participate if I don’t drink alcohol?
While tastings are part of the experience, you can still enjoy the scenic hikes, food, and learning about local products. It’s a well-rounded cultural day.

Is the tour suitable for children?
Not for children under 18, as the focus is on wine and olive oil tastings, and the physical activity may not be appropriate for young kids.

What if it rains?
The tour runs rain or shine, unless weather alerts suggest severe conditions. Be prepared with rain gear just in case.

In Closing

This tour offers a genuine slice of Tuscany’s wine and food culture in a relaxed, eco-friendly setting. You’ll love the combination of scenic hikes, historic family wineries, and authentic Tuscan cuisine—all led by passionate guides dedicated to sharing local traditions. It’s a perfect choice for those wanting a more personal, sustainable experience that blends outdoor activity with culture.

While it’s not suited for travelers with mobility restrictions or young children, it’s ideal for wine lovers, nature fans, and anyone looking for a heartfelt connection with Tuscany’s countryside. The small group size, expert guides, and focus on local, organic producers make this tour a memorable way to taste the real Tuscany.

Remember: If you’re craving a peaceful, authentic, and delicious day in Italy’s famous wine region, this experience might just become a highlight of your trip.

You can check availability for your dates here: