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Discover the charm of Tuscany with a 5-hour wine tasting tour in two family-run wineries near Florence, including stops in Greve in Chianti and San Casciano.


This 5-hour tour costs $185.77 per person and is hosted by Florence Super Tours. It is designed for those who want to explore family-run vineyards, taste genuine Chianti Classico wines, and enjoy the scenic beauty of the Tuscan countryside. The tour departs from Piazza dei Cavalleggeri in Florence and includes pickup options, making logistics straightforward.
What makes this tour particularly appealing is its focus on small groups capped at 6 people, allowing for a more intimate setting. Travelers highly appreciate the knowledgeable guides and the chance to visit two distinct wineries, each with its own character and story. The experience is ideal for wine enthusiasts, food lovers, or anyone looking to deepen their understanding of Chianti wines.
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The first stop takes place in Montefioralle, a picturesque medieval village in the heart of Chianti. Here, visitors visit a local, family-owned winery, where the winery owner shares insights into their company’s history and wine-making process. As part of the experience, guests can taste Chianti Classico alongside typical Tuscan cold cuts, cheeses, and extra virgin olive oil.
This stop lasts approximately 2 hours, with free admission to the winery. The tour offers stunning views of the Tuscan countryside and provides opportunities for short photo stops amidst the charm of Italy’s medieval architecture. Visitors often comment on the cozy atmosphere of the vineyard and the quality of the wines.

After Montefioralle, the itinerary includes a 20-minute visit to Greve in Chianti, a town famous for its small historic square and lively atmosphere. This quick stop allows visitors to view the quintessential Chianti scene—a bustling square surrounded by restaurants and bars—and soak in the local ambiance. It’s a perfect chance for quick photos or to stretch your legs before heading to the next winery.

The tour’s highlight is a visit to a stunning villa dating back to the 1400s in San Casciano in Pesa. Surrounded by an Italian garden, the villa looks like something out of a “Thousand and One Nights” storybook. Here, visitors enjoy a wine tasting of Chianti Classico alongside cured meats, cheeses, and extra virgin olive oil.
This second wine tasting lasts about 2 hours with free admission. Guests appreciate the chance to explore a beautiful medieval village and take in panoramic views of the Tuscan landscape. The villa’s historic ambiance and the quality of the local food and wine are often highlighted as standout features.

The tour starts at Piazza dei Cavalleggeri in Florence. It includes pickup options, making it easy to join without worrying about transportation. The activity ends back at the original meeting point, ensuring a smooth flow for participants. The tour operates daily between 12:00 PM and 6:00 PM, from October 2024 to June 2026.
The tour is suitable for most travelers, with comfortable shoes recommended to handle walking on uneven village streets and vineyard paths. The group size is limited to 6 people, fostering an engaging and personalized experience.
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This tour emphasizes visiting family-owned vineyards, giving insight into traditional Chianti wine production. The guides are praised for their knowledgeability and friendly manner, making the experience both educational and enjoyable. Guests have enjoyed tastings of 4-5 different wines at each winery, with some stops including snacks to complement the wine.
The focus on smaller wineries ensures visitors get to meet the owners and learn about local wine-making techniques firsthand. The scenic stops in villages like Montefioralle and San Casciano add cultural richness to the wine tasting, creating a well-rounded experience.

Throughout the tour, local foods such as cold cuts, cheeses, cured meats, and extra virgin olive oil are served alongside the wines. Guests often comment on the quality and authenticity of these pairings, which are selected to complement the Chianti Classico wines. The house wines come highly recommended, often described as excellent and memorable.

The guide, Romana, receives glowing reviews for her helpfulness, knowledge, and easy-going personality. She provides great suggestions for restaurants and takes time to explain the nuances of Chianti wines. Her enthusiasm and local insights elevate the experience, making it more than just a tasting.
Most bookings are made about 32 days in advance, reflecting high demand. The tour offers free cancellation up to 24 hours before the start, providing flexibility for travelers. Comfortable shoes are recommended for walking through villages and vineyards, and travelers should be prepared for small group intimacy.
The mobile ticket system and proximity to public transportation make access convenient, while the short duration fits well into a full day of exploring Florence or the surrounding region.
This wine tasting tour suits those interested in authentic family-run wineries and scenic Tuscan villages. It’s perfect for food and wine enthusiasts, history lovers, and anyone eager to see the real Chianti countryside. The small-group setup suits travelers who prefer a more personalized experience over large, crowded tours.
This 5-hour tour provides a balanced blend of wine, food, culture, and scenery. Its focus on family-owned wineries ensures visitors taste genuine Chianti wines and hear personal stories directly from the owners. The scenic stops and delicious local foods make it a rewarding experience for those wanting to explore the heart of Tuscany.
While it’s a shorter tour, it packs in quality wine tastings, beautiful villages, and insightful guidance. It is a great choice for anyone seeking an authentic, relaxed, and scenic wine experience near Florence.
“Amazing trip to two vineyards and Greve in Chianti with Romana. Can really recommend this tour, Romana was so helpful and easy-going. The vineyards…”
Is transportation provided on this tour?
The tour includes an optional pickup, but participants meet at Piazza dei Cavalleggeri in Florence.
How many wineries will I visit?
You visit two family-owned wineries in the Chianti region.
What foods are included with the wine tastings?
Guests enjoy cold cuts, cheeses, cured meats, and extra virgin olive oil at both stops.
How long is each winery visit?
Each winery experience lasts approximately 2 hours.
Can I cancel or reschedule?
Yes, the tour offers free cancellation if canceled at least 24 hours in advance.
Is this tour suitable for children or those with mobility issues?
Most travelers can participate; however, comfortable shoes are recommended for walking on village streets and vineyard paths.
What is the maximum group size?
The tour is limited to 6 travelers, ensuring a personal experience.
What is the price of the tour?
The cost is $185.77 per person.
What is the best time of year to book?
Bookings are popular and typically made about 32 days in advance, and the tour runs year-round from October 2024 to June 2026.
How long does the entire tour last?
The experience lasts about 5 hours total, from meeting to return, including visiting stops and tastings.