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Enjoy a half-day private tour from Florence including wine tasting at a family-run Chianti winery and a self-guided visit to the medieval town of San Gimignano for $149.81.

This half-day tour in Florence, priced at $149.81 per person, offers a focused experience of Tuscany’s renowned Chianti wine region and the picturesque town of San Gimignano. With a duration of approximately 6 hours, it combines scenic drives, local wine tastings, and cultural exploration. The tour is operated by Pek Tuscany in Limo and features a private vehicle and driver, emphasizing comfort and personalized attention.
Ideal for visitors seeking a short but immersive taste of Tuscany, this experience highlights five wines from a family-run winery and provides self-guided free time in the medieval hill town. Its group discounts and mobile ticket options make it accessible and convenient, with the flexibility of morning or afternoon departures to fit different schedules.

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The tour begins at Via del Curtatone no. 9, Florence, where your English-speaking driver meets your group. From here, you settle into an air-conditioned vehicle for a 2-hour drive along the Chiantigiana, the famous Tuscan wine road. As the vehicle winds through rolling hills, you’ll enjoy views of vineyards, cypress trees, sunflower fields, and quaint hillside villages—picturesque scenes that embody the essence of Tuscany.
This scenic drive sets the tone for the day, offering plenty of opportunities to appreciate the landscape without the hassle of navigation. The experience’s focus on comfort and flexibility makes it ideal for groups or families who want a relaxed, informative journey.

The first stop is Cantine Guidi, a well-established historic winery specializing in Chianti Classico, Super Tuscan, and Vernaccia wines. Here, visitors taste five different wines, including two glasses of Vernaccia—a crisp white wine from San Gimignano—and two glasses of Chianti Classico, known for its vibrant, earthy flavor.
The winery produces Chianti Classico, made mainly from Sangiovese grapes, and Super Tuscan wines, which blend international varieties like Merlot and Cabernet Sauvignon outside traditional DOC regulations. The winery’s long history and family ownership, spanning over a century, add to the authenticity of the tasting experience.
During the visit, guests gain insight into the different wine styles and production methods. While the tour itself is about one hour, the tasting session offers a well-rounded introduction to Tuscany’s wine traditions, making it a highlight for wine enthusiasts.

After the wine tasting, the tour advances to San Gimignano, a medieval hill town famous for its tower-filled skyline and well-preserved architecture. The town, known as the Town of Fine Towers, features over 70 historic towers that once signified wealth and power.
Visitors have approximately an hour of free time to wander the cobbled streets, admire the medieval facades, and take photographs of the walled hilltop. San Gimignano is also renowned for its saffron, Golden Ham, and Vernaccia di San Gimignano, the white wine that shares the town’s name and historic roots.
This self-guided exploration allows for a relaxed appreciation of the town’s timeless atmosphere, with ample opportunity for photos and discovering local shops, making it suitable for those who enjoy independent sightseeing.

The tour includes bottled water for refreshment, as well as five glasses of wine—specifically, two glasses of Vernaccia and two glasses of Chianti Classico (“Black Rooster”)—to ensure a genuine tasting experience. Guests benefit from private transportation in an air-conditioned vehicle, with a local driver and expert guide providing insights and ensuring smooth logistics.
The personalized nature of the tour, combined with group discounts, makes it a good option for families or small groups seeking exclusivity and tailored attention.
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The experience starts at Via Curtatone, 9, Florence, where guests meet their English-speaking driver. The tour ends back at the same meeting point, offering convenience for those staying in Florence city center.
Travelers can choose between morning or afternoon departures, providing flexibility to fit personal schedules. The private tour format ensures that your group’s pace and interests are prioritized, without the constraints of large group settings.

Rated 5 out of 5 based on three reviews, this tour is praised for knowledgeable guides, authentic family-owned wineries, and stunning views of Tuscan landscapes. Reviewers highlight personalized attention, especially from guides like Andrea, who shares engaging stories about the region’s history and wine traditions.
The self-guided visit to San Gimignano allows for a peaceful experience, even during busy seasons or holiday periods when crowds might be smaller, as noted in one review. The quality of the wine and the scenic drive are consistently appreciated.

This half-day tour offers a compact, yet comprehensive taste of Tuscany’s wine culture and medieval charm. It’s especially suited for visitors who want a personalized, relaxed exploration without committing to full-day excursions. The private transportation and flexible scheduling enhance comfort and convenience.
While the tour emphasizes wine tasting and sightseeing, it does not include extensive guided tours of the towns or the winery itself, making it ideal for those who prefer self-directed exploration after the tasting.
The private format enhances the experience for families or groups who value space and personalized interaction. The tour’s short duration makes it manageable for those with limited time in Florence or who prefer to combine other activities in their itinerary.
It’s important to note that the tour involves some walking during the San Gimignano visit, but accessibility is generally manageable, given the short duration and level of activity.
This Chianti Classic Tour with wine experience and San Gimignano visit delivers an authentic taste of Tuscany’s wine heritage and medieval charm. The personalized service, quality wine tastings, and stunning landscape views make it appealing for those wanting a short but meaningful addition to their Florence trip.
The rated 5/5 from travelers emphasizes its consistent ability to meet expectations, especially in providing expert guidance and an intimate atmosphere. It’s a good choice for wine lovers, history enthusiasts, or those simply seeking a beautiful, laid-back day in Tuscany.
“Our tour guide Andrea did a fantastic job telling us about the history of the region. The wine was fantastic and from a family owned winery dating …”
Is this tour suitable for children or non-drinkers?
Yes, the experience includes bottled water and sightseeing, making it suitable for non-drinkers or families.
What is included in the price?
The tour includes private transportation, five glasses of wine (two Vernaccia and two Chianti), bottled water, and guidance by an English-speaking driver.
Can I choose morning or afternoon departures?
Yes, the tour offers flexible departure times to suit your schedule.
How long is the drive from Florence to Chianti?
The drive lasts about 2 hours, passing through scenic Tuscan hills.
What are the stops during the tour?
You visit Cantine Guidi winery for wine tasting and San Gimignano for a self-guided walk.
Is the tour private or part of a group?
This is a private tour, ensuring personalized experience and exclusive attention.
How much time do I have in San Gimignano?
You have approximately one hour for self-guided exploration of the town.
Are there any physical requirements?
The tour involves some walking in San Gimignano, but overall, it is manageable for most participants.
What makes this tour stand out?
The family-run winery, scenic drive, and flexible schedule are key strengths, along with consistent high ratings and positive reviews.
How do I book this tour?
Booking can be done through the provider, Pek Tuscany in Limo, with options for group discounts and mobile tickets.