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Discover the charm of Tuscany with this small-group Chianti wine tour from Florence, featuring visits to two top wineries, expert-guided tastings, and a delicious lunch.
A small-group Chianti-side wine tour priced at $231.05 per person offers an intimate way to explore Tuscany’s celebrated wine region. This 5-hour experience departs from Florence with a maximum of 7 participants, ensuring personalized attention and a relaxed pace. The tour includes visits to two renowned wineries, tastings paired with local snacks, and a scenic lunch overlooking the Chianti countryside. The use of a Mercedes V class Van guarantees comfortable, air-conditioned transport throughout the day.
While the tour is designed to be straightforward and stress-free—thanks to hotel pickup and all-day transportation—it does require booking about 46 days in advance on average, reflecting its popularity. The tour’s positive reputation is backed by a perfect 5-star rating from 37 reviews, emphasizing its high value and enjoyable experience. It’s especially suited for those seeking an authentic, hassle-free wine tasting adventure with small-group intimacy.

This tour takes the hassle out of navigating the Tuscan hills by providing direct hotel pickup and all-inclusive transport. Guests don’t need to worry about driving or planning routes—just relax and enjoy the scenery. The Mercedes V class Van offers a comfortable ride through Tuscany’s picturesque landscape, with stops at two of the region’s most notable wineries.
The itinerary includes visits to Casa Emma, where tastings are paired with small local snacks, and Castello di Gabbiano, an ancient castle turned luxury hotel and winery. These stops showcase stunning cellar views and offer insights into wine-making traditions perfected in Tuscany. Both wineries may vary depending on availability, but they consistently promise quality and authentic experiences.
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The first stop, Casa Emma, provides a welcoming introduction to Tuscan wines. Visitors are treated to tastings of local reds and whites, paired with little local snacks, which enhance the flavors and give a taste of regional specialties. The 1 hour and 30 minutes spent here allows ample time to explore the cellar, learn about wine production, and enjoy the tasting in a charming setting.
This winery is known for its approachable atmosphere and high-quality offerings, making it a great first stop for those new to Italian wines or seasoned connoisseurs alike. The tasting experience here typically highlights the variety and craftsmanship involved in Tuscany’s wine scene.

The second stop at Castello di Gabbiano is equally impressive. This ancient castle has been transformed into a luxury hotel and high-caliber winery. Visitors are able to tour stunning cellars and appreciate the scenic surroundings that make this spot a favorite among wine lovers.
The 1 hour and 30 minutes spent at this winery include guided tours and tastings of premium wines, often accompanied by insights into the castle’s history and wine production methods. The cellars’ architecture and ambiance create a memorable backdrop for tasting the region’s best offerings.

A standout feature of this tour is the lunch included in the package, served amid the beautiful Chianti countryside. The meal typically features local ingredients and regional dishes, perfectly paired with the wines sampled during the day.
While the specific menu may vary, the emphasis remains on authentic Tuscan cuisine and picturesque views. The combination of good food, excellent wine, and sweeping vistas makes this part of the experience feel relaxed and indulgent.

The tour begins at Piazza Lorenzo Ghiberti in Florence at 1:15 pm, with options for near public transportation. The small group size ensures an intimate atmosphere, enabling guests to ask questions and enjoy a more personalized experience.
The use of private, air-conditioned transport means you can sit back, relax, and enjoy the scenery without any logistical stress. The full-day transport takes you comfortably between wineries and scenic stops, allowing for a leisurely exploration of the Chianti hills.
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Based on reviews, the guides like Michela and Guiliano receive praise for their knowledgeability, friendly demeanor, and ability to make the trip engaging. Their insights into the wine process and local history add depth to the tasting experience.
Guests frequently highlight the value for money and unhurried pace, noting that the tour feels personalized and flexible. The lunch at Rocca di Cispiano estate, praised as a highlight, exemplifies the thoughtful planning behind the experience.

This small-group tour is perfect for those who want to enjoy Tuscany’s wine and scenery without the hassle of driving. It suits visitors seeking an authentic, intimate experience with high-quality tastings and a scenic lunch. Its 5-star rating and glowing reviews suggest it’s ideal for wine lovers, couples, or small groups looking for a relaxed, informative day in Tuscany.
Because it is limited to 7 travelers, the tour offers a personalized touch that larger groups cannot. It’s a practical choice for anyone wanting a hassle-free day exploring Chianti’s celebrated wineries.

This small-group Chianti wine tour delivers excellent value, combining top wineries, guided tastings, and delicious local lunch in a comfortable, intimate setting. The Mercedes V class Van ensures a smooth journey through Tuscany’s rolling hills, with hotel pickup and all-day transport removing logistical worries.
The high praise from guests underscores the professionalism of guides and the quality of the experience. It’s especially suitable for those who appreciate personalized service and want to explore Chianti’s wine culture at a relaxed pace.
While the tour’s stops may vary slightly depending on availability, the core experience remains consistent: quality wines, scenic views, and engaging storytelling. For anyone seeking an affordable, enjoyable day in Tuscany, this tour offers a reliable and memorable way to experience the region’s famed wines.
“Had a very nice day with Michela. She was very knowledgeable and accommodating and the trip was wonderful. By far, the highlight was lunch at the …”
How far in advance should I book this tour?
Booking typically occurs about 46 days in advance, given its popularity.
What is included in the price?
The cost covers wine tastings at two wineries, lunch, private transportation, fuel surcharge, and hotel pickup.
What wineries will I visit?
The stops are Casa Emma and Castello di Gabbiano, though the order or specific wineries may vary based on availability.
Is the tour suitable for non-drinkers?
Yes, non-drinkers can enjoy the scenic views, food, and the comfortable transport. Tastings are optional.
How long do stops at each winery last?
Each winery stop lasts about 1 hour and 30 minutes, providing ample time for tours and tastings.
What is the start time and meeting point?
The tour begins at 1:15 pm at Piazza Lorenzo Ghiberti in Florence.
Is transportation comfortable?
Yes, the journey is in an air-conditioned Mercedes V class Van, ensuring comfort during the day.
Can service animals participate?
Yes, service animals are allowed on the tour.
Are there any physical requirements or accessibility considerations?
Most travelers can participate, but no specific accessibility details are provided.
What is the cancellation policy?
You can cancel for free up to 24 hours in advance for a full refund.
Who is the tour provider?
The experience is offered by Bespoke Italian Tours.