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Discover Tuscany’s Chianti region on this 8-hour guided tour featuring hikes, visits to 3 organic wineries, wine and food tastings, and a traditional Tuscan lunch.
This 8-hour tour in Tuscany offers a perfect blend of nature, wine, and culture, taking you through the Chianti Classico wine region. Led by knowledgeable guides like Stefano and Lorenzo, the experience includes short hikes, visits to three organic and biodynamic wineries, and a delicious Tuscan lunch. The tour departs from Panzano in Chianti, with small group sizes limited to 7 participants, ensuring an intimate and personalized journey. Priced to include wine tastings, visits to historical cellars, and a scenic drive, it’s ideal for those wanting an authentic, sustainable experience in Tuscany.
While the tour involves about 8 km of walking over uneven terrain, it’s designed to be more downhill than uphill, making it accessible for most physically able participants. The tour also emphasizes supporting local producers and sustainable tourism, making it both a memorable and responsible way to explore Tuscany’s countryside.


This tour begins with a walk through the Conca d’Oro, a stunning natural amphitheater where the best Chianti Classico wines are made. The scenic hike offers insight into the land that shapes the region’s famous wines. The guides lead you through vineyards, giving a behind-the-scenes look at wine and olive oil production. The walking is about 8 km and involves uneven terrain with more downhill sections, so comfortable, hiking shoes are recommended.
The hike sets the perfect tone for the day, blending natural beauty with agricultural craftsmanship. As the tour progresses, visitors gain a deeper understanding of the local landscape, plants, and traditional practices that define Tuscan winemaking.
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One of the highlights is the visit to a historic winery from the 12th century, housed in the second oldest building in Panzano in Chianti. This medieval post has been transformed into a charming wine cellar. Guests will enjoy tastings of marvelous wines in this stunning location, appreciating the authentic atmosphere that reflects the region’s history.
The wine cellar tour offers a chance to learn about vintage wine production and the traditions that have been passed down through generations. The passion of the local family running the winery makes the experience especially intimate and memorable.

After the first winery visit, the group boards a minivan for a scenic drive along little roads in the Chianti region. This part of the tour transports guests through picturesque landscapes filled with vineyards, olive groves, and little villages.
The drive provides perfect opportunities for photos and resting between hikes, while also allowing the guides to share fascinating stories about the region’s history and local traditions. The hidden routes chosen for this journey are part of what makes this tour special.

The lunch stop is a delicious Tuscan meal paired with wines produced by three generations of local farmers. The tasty dishes often include local specialties, giving guests a true taste of Tuscany. At some stops, the lunch may be postponed to the next winery visit to accommodate production schedules.
This meal acts as a refresher and social centerpiece of the day, allowing participants to relax and discuss their impressions amid beautiful vineyard views. The pairing of food and wine highlights the region’s culinary richness.
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The last stop introduces a contemporary winery built at the top of hilltops, overlooking the medieval castle of Montefioralle. This modern facility combines state-of-the-art techniques with traditional knowledge. The wine tastings here showcase the innovative approach to wine production while respecting the region’s heritage.
Guests can admire artistic architecture and breathtaking views while sampling some of the finest wines of the tour. The setting makes it a perfect finale to the day, blending modernity with history.
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Guides like Stefano and Lorenzo earn high praise for their expertise and passion. They explain winemaking processes, share regional stories, and answer questions with patience and depth. Their flexibility and local knowledge allow for adjustments when weather impacts the schedule, such as rainy days or winery supply issues.
The guides’ friendly demeanor and willingness to share insights turn a standard wine tour into a personal journey into Tuscany’s landscape and culture. Their storytelling enhances the authenticity of each visit.

The tour starts at the Café Lietta in Panzano in Chianti, with guests advised to arrive 10 minutes early. The meeting point features a sign or guide with an Out of the Box Florence van. The transport between stops is by minivan, with approximate 1-hour drives connecting the locations.
Because large luggage or backpacks are not allowed, travelers should pack light and wear comfortable clothing suited for outdoor walking. The weather can vary, so sun protection and water are essential. The tour is not suitable for pregnant women, those with mobility issues, or children under 18.

This tour emphasizes supporting small, organic, and biodynamic wineries. Participants learn about sustainable farming practices and get the chance to meet local producers directly. The experience encourages responsible tourism by promoting local businesses and traditional methods.
Since some products may be unavailable due to winery schedules or harvest timelines, the tour providers often offer alternative routes to maintain quality and experience.

The main strengths of this tour include personalized attention, authentic visits, and scenic hikes that are not overly strenuous. The small group size fosters a relaxed atmosphere and deeper connections with guides and producers.
A notable consideration is the physical demand, with uneven terrain and up and down hills. Those with mobility issues or back problems should assess their comfort with outdoor walking over rough ground. The rain or shine policy means guests should prepare for variable weather.
This guided tour provides a rich taste of Tuscany’s landscapes, wine, and food in a single day. The combination of hikes, vineyard visits, and culinary delights creates a balanced experience that immerses participants in the region’s authentic charm.
The focus on sustainability, local producers, and historical sites ensures this tour is meaningful as well as enjoyable. It’s particularly suited for those who love outdoor activity combined with wine appreciation in an intimate setting.
What is included in the tour price?
You get guided visits to 3 wineries, wine tastings, a Tuscan lunch, and scenic transportation between stops.
How long is the walking involved?
Expect around 8 km of walking throughout the day, mostly on uneven terrain with some ups and downs.
Is the tour suitable for children?
No, this tour is not suitable for children under 18 or people with mobility issues.
What should I bring?
Bring sunglasses, sun hat, hiking shoes, water, biodegradable sunscreen, and comfortable clothes for outdoor walking.
Can the tour be canceled if weather is bad?
Yes, the tour is rain or shine. It is canceled only in case of orange or red weather alerts.
How large are the groups?
The tour operates with small groups limited to 7 participants for a more personalized experience.