Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Tuscany's Chianti region with a small group tour from Florence, visiting organic family wineries, tasting Chianti Classico, and enjoying a Tuscan lunch.


This 8-hour small group tour from Florence offers a comprehensive journey into the heart of Tuscany’s Chianti region. Led by Matteo, a knowledgeable local sommelier, the experience combines wine tasting, cultural stories, and a taste of authentic Tuscan cuisine. With a limit of 8 participants, the tour guarantees a more intimate and personalized experience compared to larger group excursions.
The tour stands out for its focus on off-the-beaten-track wineries, all practicing organic farming, which emphasizes both quality and environmental responsibility. It’s particularly suited for wine lovers who appreciate authentic stories behind wines and enjoy picturesque scenery, but it also suits anyone interested in discovering Tuscany’s culinary heritage in a relaxed setting.
If wine interests you, we've examined these other wine experiences in Florence

The tour begins at Piazza Lorenzo Ghiberti, 5r, with the meeting point conveniently located at the Sfoglia Re restaurant. Travelers are advised to bring comfortable shoes, sun protection, a camera, and water for a full day of exploration. Participants are transported comfortably in a small van, which allows for easy access to each winery and scenic spots.
The small group size ensures a quiet, unrushed journey. The transfer times between stops range from 20 to 30 minutes, giving ample time to enjoy the landscape and prepare for each visit. It’s clear that the tour is designed for relaxation, with pacing that allows savoring every moment.

The tour includes three visits to family-owned wineries, each offering a distinct experience. The first stop lasts about 1.5 hours, giving enough time for a guided tour and tasting. The second stop is slightly longer, around 2 hours, providing a deeper look into winemaking processes. The final winery visit is again 1.5 hours, wrapping up the wine exploration.
These wineries are off the beaten path, away from crowded tourist spots, which means visitors get a more authentic view of local traditions. All of them practice organic farming, highlighting the commitment to sustainable practices. At each location, the winery owners or guides share stories about their history, passion, and the dedication involved in producing Chianti Classico wines.

A highlight of the tour is the exclusive tasting of Chianti Classico wines at each winery. The guide, Matteo, explains the nuances of the wines and their connection to the land and climate of Tuscany. Participants learn how to pair Chianti with local foods, enhancing their appreciation of the wines.
The tour includes an authentic Tuscan lunch, featuring locally inspired dishes. This meal is paired with the wines tasted during the day, showcasing the art of food and wine pairing. The focus on local ingredients and traditional recipes adds a genuine flavor to the experience.
More Great Tours Nearby
Another notable aspect is the opportunity to taste a variety of Italian cheeses at a nearby local market. This adds an extra dimension to the culinary journey, providing insight into Tuscany’s cheese-making traditions. The cheese tasting complements the wine experience and allows for a broader appreciation of regional flavors.
Throughout the tour, visitors enjoy stunning views of rolling hills, vineyards, and Tuscany’s characteristic landscapes. The scenery provides a perfect backdrop for photography and relaxation. The breathtaking vistas reinforce the peaceful, unhurried nature of this experience.
Participants are encouraged to soak in the beauty of the countryside while learning about the region’s history and agricultural practices from the guide.

Matteo’s storytelling style is warm, friendly, and informative. As a local Florentine, he shares fascinating insights into Chianti’s history, winemaking techniques, and eco-friendly practices at each winery. His passion for Tuscan culture enriches the experience, making each visit not just about tasting wine but understanding its cultural significance.
His ability to explain complex processes in an accessible way makes the tour engaging for both seasoned wine enthusiasts and those new to wine tasting.
This tour is suitable for most adults interested in wine, food, and Tuscany’s landscapes. It is not designed for children under 10, pregnant women, wheelchair users, or those under 18. Participants should wear comfortable shoes, carry sun protection, and come prepared for the outdoor elements.
The tour emphasizes relaxation and enjoyment, with plenty of time to savor each stop. It’s an ideal choice for those who prefer a smaller, more personal tour experience over larger groups.

Booking can be done with the flexibility to reserve now and pay later. Cancellations are free up to 24 hours in advance, offering peace of mind for travelers with flexible plans. The tour runs daily, with available starting times that can be checked based on availability.
This small group tour offers an authentic and relaxing taste of Tuscany’s Chianti region, combining wine tasting, scenic views, and local cuisine. The focus on family-owned wineries practicing organic farming ensures a genuine connection to the land and tradition. The expert storytelling of Matteo makes each visit engaging and educational.
While it’s a full-day experience, the pacing and scenic stops make it enjoyable without feeling rushed. It’s particularly ideal for wine enthusiasts and those interested in Tuscany’s culinary culture. The limited group size ensures a more intimate atmosphere, perfect for savoring the flavors and stories of Chianti.
Is this tour suitable for children?
No, the tour is not suitable for children under 10, children under 18, or pregnant women.
What should I bring?
Participants should bring comfortable shoes, a sun hat, a camera, sunscreen, and water for the day.
Can I cancel the booking?
Yes, cancellations are free up to 24 hours in advance. You can reserve now and pay later for flexibility.
What makes this tour different from larger wine tours?
The small group size (limited to 8 people) allows for a more personalized experience and direct interactions with the winemakers.
Is lunch included?
Yes, the tour features a traditional Tuscan lunch paired with Chianti wines, highlighting local ingredients and flavors.