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Discover the charming Chianti hills and San Gimignano with this private 8-hour tour featuring wine tastings, a Tuscan farm lunch, and scenic stops.

This private 8-hour tour from Florence offers an engaging way to experience the stunning landscapes and authentic flavors of Tuscany. Priced at $269.39 per person, it combines scenic drives, cultural stops, wine tastings, and a traditional Tuscan lunch. Designed for groups of friends or family, the tour ensures personalized attention with private transportation and a knowledgeable local driver.
The itinerary includes visits to San Gimignano, renowned for its medieval towers and breathtaking views, along with stops at Castel Monteriggioni and two charming wineries. With all wine tastings included, you can indulge freely in about 10 glasses of Chianti and other regional wines. The tour is ideal for those seeking a balanced mix of sightseeing, wine, and authentic Tuscan cuisine, though it’s worth noting that the trip involves some walking around San Gimignano and Monteriggioni.

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The tour begins with a pickup at your location in Florence, whether it be a hotel, B&B, or private apartment. From there, your expert driver takes you on a scenic ride through the iconic Chianti countryside, characterized by rolling hills, vineyards, olive groves, and cypress trees. This drive exemplifies the picturesque beauty that makes Tuscany so beloved, setting a relaxed tone for the day.
The journey culminates at San Gimignano, a UNESCO World Heritage site renowned for its medieval towers and panoramic views. Here, visitors have about an hour for a self-guided tour, exploring the town’s narrow streets and historic architecture at their own pace. The views of the surrounding countryside are particularly striking, making it a highlight of the day.

The centerpiece of the wine experience is the visit to Podere La Marronaia- Le Colonne Biodynamic Winery & Farm, a family-run operation committed to biodynamic winemaking. Here, the group enjoys a fabulous Tuscan lunch, which includes homemade pasta, bruschetta, pecorino cheese, and extra virgin olive oil. The setting is authentic and relaxed, giving insight into traditional Tuscan farm life.
Wine tastings at this winery include a variety of regional wines such as Chianti, Chianti Riserva, Vernaccia, Chianti Classico, and Super Tuscan. Expect to sample around 10 glasses during your visit, gaining a thorough appreciation for the depth and richness of Tuscan wines. The family’s hospitality and the quality of the wines make this stop stand out.

After lunch, the tour moves on to Monteriggioni Castle, an ancient fortress built between 1213 and 1219 by the Sienese. Its imposing walls and towers served as a strategic outpost against Florence and have since become a symbol of medieval strength. The 30-minute visit allows time to stroll around the fortress walls and take in the views.
This stop provides an authentic glimpse into medieval defensive architecture and offers excellent photo opportunities. While the castle is free to enter, the experience of walking its ramparts and imagining its historical significance makes it a memorable part of the day.

The last stop takes place at Fattoria Lornano, a longstanding Tuscan winery nestled in the Chianti region. This 45-minute visit features a second wine tasting session, giving guests the chance to sample some of the most notable wines of the region, including Chianti and Chianti Riserva.
The winery’s long history in wine production, combined with its authentic Tuscan setting, enhances the tasting experience. You’ll find the wines here are considered the “king of wines,” and the tasting is designed to deepen your appreciation for Chianti’s distinctive qualities.

Throughout the day, wine tastings are a key feature, with about 10 to 12 glasses of regional wines included. The variety spans Chianti, Chianti Riserva, Vernaccia, Chianti Classico, and Super Tuscan options, providing a broad tasting experience. The tastings take place at two different farms, highlighting the diversity of Tuscan winemaking.
The lunch in a traditional Tuscan farm is a highlight for many, offering homemade pasta, bruschetta, pecorino cheese, and extra virgin olive oil. The meal is hearty and authentic, emphasizing regional flavors and culinary traditions. The inclusion of truffle oil adds a special touch to the meal.

The tour’s private transportation ensures a comfortable and relaxed day. The vehicle is air-conditioned, perfect for the warm Tuscan climate. The local expert driver adds to the experience by sharing insights about the region’s history and culture.
Because the tour is private, only your group participates, allowing for a flexible pace and personalized attention from the guide. This setup makes it ideal for those looking for an intimate exploration of Tuscany without the crowds often found on larger tours.

The tour starts promptly at 9:00 am, with pickup available from your accommodation. The group discounts and mobile ticket options make booking convenient, and the tour is designed to accommodate most travelers, with no specific physical requirements noted.
The experience is fully refundable if canceled at least 24 hours in advance, providing peace of mind for those making last-minute plans. Since it’s a private tour, no other groups are involved, ensuring an exclusive experience.
This tour appeals to visitors seeking a comprehensive and personalized day trip from Florence, with a focus on wine, food, and scenic beauty. The combination of cultural stops and tastings makes it suitable for food and wine enthusiasts, as well as those interested in medieval architecture and Tuscan landscapes.
It’s well-suited for small groups or families who want an intimate experience with flexibility and expert local insights. Travelers should be comfortable with some walking and be prepared for a full-day tour that involves both outdoor sightseeing and seated tastings.
The Sweet Hills of Chianti & San Gimignano tour offers a well-rounded taste of Tuscany’s natural beauty, historic towns, and world-class wines. The private setting and all-inclusive approach—covering tastings, lunch, and transportation—make it a convenient and enjoyable way to explore the region.
While the itinerary covers several highlights, it’s also flexible enough to suit small groups looking for a personalized experience. The biodynamic winery visit and medieval fortress add extra layers of authenticity, making this tour a fantastic choice for those eager to see authentic Tuscany beyond Florence.
“Such a wonderful tour from beginning to end! Stefano was a great guide… his kindness and knowledge made him a join to be around. San Gimignano …”
What is included in the tour price?
The tour includes private transportation, two wine tastings, a 3-course Tuscan lunch, bottled water, and the services of a local expert driver.
How long is the tour?
The tour lasts approximately 8 hours, starting at 9:00 am with flexible timing for each stop.
Are there any physical requirements?
The tour is suitable for most travelers, though some walking is involved at San Gimignano, Monteriggioni, and the wineries.
Can I cancel the tour?
Yes, you can cancel free of charge up to 24 hours before the start time for a full refund.
Is this tour suitable for wine lovers?
Absolutely. The tour features wine tastings at two biodynamic wineries, with a total of about 12 glasses of regional wines included.
Who is the tour provider?
The tour is operated by Pek Tuscany in Limo, known for personalized private experiences in Tuscany.
Can I customize this tour?
As a private experience, it offers some flexibility, but all activities are structured within the itinerary provided.
What makes this tour different from other Tuscany day trips?
The private setting, biodynamic wineries, and authentic Tuscan lunch distinguish this experience from larger group tours.
Is lunch included?
Yes, a 3-course Tuscan farm lunch with regional specialties is part of the package.
What is the best time to book?
The tour is typically booked about 51 days in advance, making it advisable to reserve early for preferred dates.
This Sweet Hills of Chianti & San Gimignano tour combines scenic beauty, cultural richness, and culinary delights into one memorable day—perfect for those who want an authentic taste of Tuscany in a private setting.