Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Imagine a day spent meandering through rolling hills dotted with vineyards, stopping at quaint medieval villages, and tasting some of Italy’s most celebrated wines. That’s precisely what this private Chianti wine tour from Florence promises — a mix of scenic beauty, authentic wine experiences, and expert-guided insight. With a reputation for excellent reviews and a well-rounded itinerary, it’s a popular choice among wine lovers and culture seekers alike.

One of the things we really love about this experience is the seamless combination of sightseeing and wine tasting, especially the opportunity to visit two wineries in the Chianti region. Plus, the fact that it’s a private tour means a more personalized, flexible experience — perfect for those wanting a more intimate day out. On the flip side, the price might be a consideration for some, especially since wine tastings and lunch are extras. Still, for the level of quality and the depth of experience, many find it well worth the cost.

This tour suits travelers who have a love for wine, history, and scenic landscapes, and who prefer hassle-free logistics like hotel pickup and drop-off. If you’re after a relaxed yet immersive taste of Tuscany, this tour could be just what you’re looking for.

Key Points

• Private, personalized experience tailored to your group’s pace and interests.
• Scenic drive through Tuscany’s iconic hills to San Gimignano and Chianti wineries.
• Expert guides and drivers make the day informative and comfortable.
• Flexible options for lunch and wine tastings, allowing customization.
• Comfortable transportation, including air-conditioned Mercedes-Benz vehicle with WiFi.
• Authentic local wine experiences, with visits to two different wineries.
• Stunning panoramic views from Piazzale Michelangelo and San Gimignano.
• Authentic small-town charm in San Gimignano’s medieval streets.

The Experience: What to Expect from Start to Finish

Starting Point: Piazzale Michelangelo — The Perfect Panorama

Your day kicks off at Piazzale Michelangelo in Florence, a spot loved by both locals and visitors for those sweeping views of the city. Here, you’ll get a quick 15-minute window to soak in stunning vistas of Florence’s skyline and the Arno River — a photo-op that sets a perfect tone for your day. The tour begins at 9:00 am, giving you plenty of time to enjoy the morning light.

The view from Piazzale Michelangelo isn’t just a pretty backdrop; many reviewers mention how this vantage point feels like a special introduction to the Tuscan landscape.

The Drive to San Gimignano — A Scenic Journey

After meeting your driver, you’ll hop into a luxurious, air-conditioned Mercedes-Benz vehicle with WiFi on board — a nice touch for passing the time or sharing your excitement. The drive into the Tuscan countryside is about two hours, during which you can relax and enjoy the shifting landscape of rolling hills, cypress trees, and vineyards.

Traveling with a professional driver means no worries about navigating or parking, and you get to focus on the views and the anticipation. Multiple reviews highlight how Gino, Gino, and Luigi (the guides mentioned in reviews) make the trip informative and engaging, sharing insights about the region’s winemaking traditions and local culture.

Exploring San Gimignano — Medieval Charm

Next stop is San Gimignano, a UNESCO World Heritage site celebrated for its medieval towers and well-preserved walls. Here, you’ll have around two hours to wander at your own pace. Many guests rave about how personable and knowledgeable guides like Gino and Luigi are, adding layers of history and fun facts as you stroll through narrow alleys and browse artisan shops.

The panoramic views from San Gimignano’s vantage points are unforgettable, and it’s easy to see why this town is a favorite for travelers seeking authentic Italian charm. One reviewer mentioned that Gino’s knowledge made the experience feel very personal, turning an ordinary visit into an engaging history lesson.

Winery Visits: Authentic Wine Production and Tastings

The core of the tour lies in visiting two wineries — often Farm Sant’Appiano and a winery along the Chiantigiana road, though the exact locations may vary depending on availability. These stops typically last around two hours each, and while the tour price does not include the wine tastings, many guests opt to indulge. Tasting fees are around €30 per person, with the option to upgrade to a lunch paired with wines for about €50-60.

Guests rave about the opportunity to see how wine is produced, not just sip it. The wineries often offer insights into the winemaking process, vine cultivation, and regional differences that enhance appreciation. As one reviewer put it, “the wineries were quite nice and the tastings were great,” highlighting the value of these visits.

The Chianti Road — Breathtaking Views

On your way back to Florence, you’ll traverse the Chiantigiana road, a highlight in itself. Several reviews mention how this part of the trip offers spectacular views of hills, vineyards, and olive groves. It’s the perfect photo opportunity and a chance to appreciate just how scenic the region truly is.

Return to Florence — Concluding the Day

After about 45 minutes along the Chianti road, your driver will return you to Florence, completing what many describe as a well-paced, enriching day. The tour wraps up roughly in the early evening, leaving you with memories of stunning vistas, fascinating wine insights, and charming medieval towns.

Authentic Insights from Travelers

Reviewers consistently mention the guides’ extensive knowledge, friendliness, and ability to make the tour feel personalized. Michelle loved how Luigi’s kindness and expertise made the experience stand out, while Brandon appreciated Gino’s wealth of local knowledge and how he managed to make everything feel seamless. One guest noted that the wineries “were amazing” and that the lunch option was “awesome,” emphasizing the overall quality of food and wine.

Others praised the stunning views and appreciated the flexibility to upgrade to lunch, making the day more indulgent. Many loved San Gimignano’s medieval charm, noting it as a highlight — especially with guides who could tell stories and share history that brought the town to life.

Practical Details and Tips

Transportation: The use of a Mercedes-Benz vehicle ensures comfort and luxury throughout the day. The inclusion of WiFi is a bonus, making it easier to share photos or stay connected.

Timing: Starting at 9:00 am, the tour lasts approximately 7 to 8 hours, which balances sightseeing, wine tasting, and travel time without feeling rushed.

Group Size: As a private tour, this experience is limited to your group, which guarantees intimacy and flexibility.

Cost and Value: At $319.30 per person, the tour is on the higher end, but many travelers find the value justified by the personalized service, quality of visits, and ease of logistics. Remember that wine tastings and lunch are additional costs if you wish to indulge.

Booking in Advance: This tour is popular and tends to be booked about 68 days in advance, so securing your spot early is advisable.

The Sum Up: Who Is This Tour Best For?

This Chianti Wine Tour from Florence offers a beautifully balanced mix of sightseeing, wine education, and regional charm. It’s a fantastic choice for wine enthusiasts wanting to explore Tuscany’s wine-making tradition without the hassle of planning logistics. The private setup suits couples, small groups, or anyone looking for a more personalized experience.

The scenic drive, charming medieval town, and visits to two wineries ensure a well-rounded day that appeals to those who appreciate authentic local flavors combined with cultural insights. The optional lunch adds extra value for those eager to indulge in regional specialties along with their wines.

If you’re after a luxurious yet authentic taste of Tuscany, with knowledgeable guides and stunning vistas, this tour checks all the boxes. Just be prepared to pay a little extra for tastings and lunch if you want the full gastronomic experience. Overall, it’s a memorable way to see Tuscany’s famous landscapes and savor its wines in style.

FAQ

Is hotel pickup included?
Yes, the tour includes pickup and drop-off from your hotel within Florence, making the experience smooth and stress-free.

How long is the total tour?
The entire experience lasts about 7 to 8 hours, including travel time, sightseeing, and winery visits.

Can I customize the wine tasting and lunch?
While the tour includes options to upgrade to wine tastings and lunch on the day, these are paid separately, and availability may vary.

What kind of vehicle is used?
A Mercedes-Benz vehicle with air conditioning and WiFi is used for transport, ensuring comfort throughout the day.

Are children allowed?
Most travelers can participate, but the tour is primarily designed for adults, especially since wine tastings are not included for minors.

Is the tour suitable for those with mobility issues?
The stops involve walking through town and winery areas; guests with mobility concerns should inquire beforehand.

What’s the best time of year to do this tour?
Spring and early fall offer ideal weather and scenery, but the tour runs year-round, weather permitting.

Are wine tastings included in the price?
No, tastings are an additional cost, typically €30 per person — but many guests find it well worth the extra for the experience.

How many wineries will I visit?
Typically two wineries, but this can vary depending on availability.

Do I need to speak Italian to enjoy this tour?
No, guides are fluent in English and will share detailed insights and stories to enhance your experience.

This private Chianti wine tour from Florence presents a perfect balance of scenic beauty, culture, and wine education — tailored for those who want a relaxed yet enriching day in Tuscany. Whether you’re a wine novice or connoisseur, it offers enough flexibility and authenticity to make your Tuscan adventure truly memorable.