Florence: Hiking Tuscany & Chianti wine 3 wineries and lunch

Exploring Tuscany on Foot and Wine: A Detailed Look at the Chianti Hiking and Wine Tour

If you’re dreaming about a day in Tuscany filled with scenic walks, local wines, and delicious food, this 8-hour tour from Florence might just be what you need. We’ve reviewed it in detail to help you decide if it fits your travel style and expectations.

What makes this experience stand out? First, the blend of walking in nature with visits to small, family-run wineries offers a genuine taste of Tuscan life. Second, the small group size means you get more personalized attention and a relaxed atmosphere. Third, the focus on sustainable, organic practices aligns with eco-conscious travel trends.

A possible caveat is the terrain, which involves uneven paths and some ups and downs — so comfortable footwear is a must. This tour suits those who love a mix of outdoor activity, culture, and wine tasting, especially if you’re eager to support local producers and enjoy authentic Tuscany away from mass tourism.

You can check if your dates are available here:

Good To Know

• Small Group Experience: Limited to 7 participants for a more intimate visit.
• Authentic Visits: Tour includes 3 organic/biodynamic wineries run by local families.
• Scenic Walks: 8 km of accessible paths through vineyards and olive groves.
• Culinary Delights: Tasting of wines, extra virgin olive oil, cheese, salami, ham, and a Tuscan lunch.
• Sustainable Focus: Emphasis on supporting local, eco-friendly producers.
• Expert Guides: Knowledgeable guides who share insights on wine, olive oil, and region history.

Why This Tour Is Worth Considering

This experience offers more than just wine tasting; it’s a full-day adventure through the landscapes and culinary traditions of Tuscany. The combination of walking in beautiful natural surroundings and visiting family-run wineries creates a balanced mix of activity and culture that appeals to many travelers. The small group size ensures that you won’t feel lost in a crowd, making it easier to ask questions and connect with your guide.

The price of around $239 per person might seem steep, but when you consider the inclusion of transportation, guided hikes, visits to three wineries, lunches, and tastings, it presents quite a good value. You’ll gain deep insights into wine and olive oil production, taste a variety of local products, and enjoy a scenic journey through Chianti’s iconic landscapes.

Detailed Breakdown of the Experience

Starting Point and Transportation

Your day begins in Florence, with a pickup that depends on your chosen option. The journey into Tuscany’s rolling hills is by air-conditioned minivan, which makes the roughly one-hour ride comfortable and relaxed. This is especially appreciated on hot days or if you’re tired from previous activities.

The small group size (up to 7 participants) ensures a cozy atmosphere where you get personalized attention. The guide, who is fluent in English, Italian, and Spanish, is key to making the day engaging and educational.

More Great Thing To Do Nearby

First Stop: Conca d’Oro Walk and Winery Visit

Your adventure kicks off with a walk through Conca d’oro, described as a “magnificent natural amphitheater,” where the best Chianti Classico wines are produced. The walk is gentle, about 8 km on accessible paths, but it involves some uneven terrain, ups and downs, so good shoes are vital.

Kate’s review highlights how Lorenzo, the guide, managed to turn around some rain disruptions by proposing alternative activities and small town visits, showing the flexibility that’s built into the experience. Exploring vineyards and olive groves here sets the tone for the day, immersing you in the region’s agricultural heritage.

The 12th Century Family Winery

Next, you’ll visit a family-run winery dating back to the 12th century — one of the most historically significant stops. This medieval post-turned-winery provides a stunning backdrop for tastings. Here, you’ll get to see the wine cellar and learn about traditional wine-making techniques.

Jessica’s review emphasizes the warm hospitality of the owners and the delicious lunch prepared by the family, including starter and pasta dishes, paired with local wines. The personal stories and pride from the winemakers make the tasting even more meaningful.

Walking Through Olive Groves and Vineyards

After the first winery, the group continues to stroll through olive groves and vineyards, soaking in the landscape and the scent of herbs and wildflowers. Lorenzo’s storytelling about local fruits and flowers adds color to the walk, making it more than just a physical activity.

Second Winery and Lunch

The next stop is a second winery operated by three generations of farmers. The wines here are described as marvelous — a true reflection of the region’s dedication to quality. A tasting session is scheduled alongside a carefully prepared Tuscan lunch featuring local specialties.

Frances’s review notes how Lorenzo’s infectious passion for wine and the region enhances the experience, making it more engaging. Sometimes, the lunch might be postponed to the next winery, but the focus remains on savoring local flavors and understanding the nuances of regional wines.

The Modern Art-Inspired Winery

The final winery offers a contrast with its modern design, created by Italian artists and positioned majestically on hilltops overlooking Montefioralle, a charming castle village. Here, modern techniques blend seamlessly with traditional knowledge, producing a diverse range of wines.

This stop provides a great opportunity to learn about contemporary wine-making methods while enjoying stunning panoramic views.

Return to Florence

After these immersive experiences, you’ll hop back into the minivan for the return journey, ending where you started. The entire day is balanced between educational insights, scenic beauty, and tasting pleasures.

What Travelers Say: Authentic Insights

Kate’s review highlights how Lorenzo “gave us many backup adventures” during heavy rain, illustrating the tour’s flexibility. She also appreciated meeting local wine and olive oil makers, describing the experience as “very cool,” emphasizing the authentic connection with producers.

Frances raves about Lorenzo’s passion and knowledge, stating that the hike was beautiful and that the connection to the region’s history and culture was palpable.

Jane loved the olive harvest observation and how the tour was “a highlight of our trip,” offering a good break from museums and city life. Jessica found the trekking reasonable for any fitness level and was impressed by the pride of the vineyard owners.

These reviews underline a key strength: guides who are passionate and well-informed, making the experience engaging and authentic.

Practical Details and Tips

Duration: 8 hours, with starting times available based on your booking.

Cost: Around $239 per person, which covers transportation, all tastings, lunch, and guided walks. While slightly premium, the inclusion of multiple wineries and food tastings offers solid value for lovers of wine and outdoor activities.

What to Bring: Sunglasses, sun hat, comfortable hiking shoes, water, biodegradable sunscreen, weather-appropriate clothes, and sports shoes.

What Not to Bring: Luggage or large bags, backpacks, as space and practicality are limited during the walk.

Weather: The tour proceeds rain or shine, only canceling with significant weather alerts. The terrain can be uneven, so sturdy shoes are essential.

Restrictions: Not suitable for pregnant women, children under 18, or those with mobility or medical issues.

Concluding Thoughts: Is This Tour for You?

This tour offers a well-rounded taste of Tuscany’s wine, food, and landscapes in an intimate setting. If you love outdoor activities combined with cultural and culinary experiences, you’ll find it rewarding. The focus on small-scale, family-run wineries gives you a deeper connection to the region and its traditions.

It’s perfect for travelers who appreciate a less commercialized, more authentic encounter with Tuscany’s countryside. The inclusion of guided walks, tastings, and local storytelling ensures you’ll leave with more than just photos — you’ll take home insights and memories.

While the physical activity might be a consideration for some, the accessible paths and relaxed pace make it suitable for most. Be prepared for uneven terrain, and you’ll enjoy a delightful day exploring Tuscany’s best-kept secrets.

FAQ

Is transportation provided? Yes, the tour includes transportation by air-conditioned minivan from Florence and back.

How long is the walking? You’ll walk about 8 km on accessible, though uneven terrain, suitable for most fitness levels.

Are the wineries family-run? Yes, all three wineries are small, family-operated farms that focus on organic and biodynamic practices.

Is lunch included? Yes, you’ll enjoy a Tuscan lunch featuring starters, pasta, and local wines, usually at one of the wineries.

What wines will I taste? Expect a total of 11 wines across the three wineries, paired with cheeses, salami, and ham.

Can I do this tour in bad weather? The tour runs rain or shine, but significant weather alerts may cause cancellations. Bring weather-appropriate clothing.

Is this suitable for children or pregnant women? No, it’s not suitable for children under 18 or pregnant women due to the physical activity and wine tastings.

What should I wear? Comfortable clothes, sun protection, and sturdy shoes for walking. Bring water and sunscreen.

How many people are in the group? The tour is limited to 7 participants for more personalized attention and a relaxed atmosphere.

This carefully curated experience delivers a genuine taste of Tuscany’s landscapes, wines, and culinary traditions. Whether you’re a wine lover, outdoor enthusiast, or simply seeking an authentic adventure, it’s a day that promises discovery and delight.

You can check if your dates are available here: