Semi Private Deep Wine Chianti and San Gimignano from Florence

If you’re seeking a way to enjoy Tuscany’s celebrated countryside, delicious wines, and historic towns without the chaos of large bus tours, this semi-private Chianti and San Gimignano experience could be just what you need. Designed for small groups, it offers a more personalized and relaxed way to soak in the region’s beauty, historic charm, and, of course, its world-famous wines.

What makes this tour stand out? First, the small-group setting ensures more individual attention from guides and more meaningful interactions. Second, the stunning panoramic views from Piazzale Michelangelo and San Gimignano promise picture-perfect moments. Lastly, the quality of wine and food experiences — from tastings at local wineries to a hearty Tuscan lunch — really elevates the entire day.

The only thing to consider? The drive through Tuscany’s winding roads can be a bit long and occasionally bumpy — so if you’re prone to carsickness, pack some motion sickness remedies or be prepared for scenic but twisting rides.

This tour suits travelers who value authentic, intimate experiences, and those eager to combine scenic landscapes with genuine wine tasting and local cuisine. If you appreciate knowledgeable guides and a leisurely pace, this will likely be a highlight of your Florence visit.

This experience made our article of Our Picks For The 13 Best Wine Tours In Florence.

Key Points

• Intimate small-group setting for personalized service and better interaction
• Stunning panoramic views of Florence and Tuscany landscapes
• Diverse wine tastings at multiple wineries, showcasing Chianti’s best
• Authentic Tuscan meal paired with regional wines
• Time in San Gimignano for exploring a picturesque medieval town
• Comfortable transportation in an air-conditioned Mercedes van
• All-inclusive experience with Wi-Fi, bottled water, and a prosecco toast
• Free hotel pickup and drop-off in Florence

A Closer Look at the Itinerary

Starting at Piazzale Michelangelo

Your day begins early, with pickup from your Florence hotel around 8:00 AM. A short 15-minute drive takes you to Piazzale Michelangelo, a must-visit spot for anyone with a camera. Here, you’ll be treated to spectacular views of Florence’s skyline, including the Duomo and Palazzo Vecchio, all framed by rolling Tuscan hills. This is an ideal spot for a quick photo and to appreciate the city’s beauty from above. The large square features a replica of Michelangelo’s David in bronze, adding to the artistic vibe.

Exploring San Gimignano

Next, a scenic hour-long drive transports you to San Gimignano, a UNESCO World Heritage site famous for its medieval towers that punctuate the skyline like something from a fairytale. Here, you’ll have about 1 hour and 25 minutes to wander this ancient walled city. Reviewers highlight its charm, especially the chance to enjoy famous gelato at one of the many local shops — a must-do on any visit. The streets are full of history, from medieval architecture to artisans’ shops, perfect for wandering and snapping photos.

Chianti Countryside and Wine Tasting

By 10:55 AM, you’ll leave San Gimignano for a 50-minute drive to a picturesque farmhouse in the Chianti region. This part of Tuscany is responsible for some of Italy’s most renowned wines, and here you’ll get a real taste of it. The farmhouse features a cellar where you’ll explore the wine-making process and sample several Chianti wines. Reviewers appreciate the knowledgeable guides who make the tasting engaging and educational.

The highlight? A hearty Tuscan lunch paired with regional wines, including cheeses, salami, and local olive oil. The food is often described as delicious, and the setting’s views of Tuscany’s rolling hills make it a perfect backdrop for the meal. One reviewer notes, “We bonded with other travelers over a fabulous luncheon, learning how to really read a label,” emphasizing the authentic, communal vibe.

Final Stop at San Michele a Torri

In the afternoon, a 25-minute drive takes you to San Michele a Torri, a family-run winery where you’ll taste even more Chianti wines—crucial for any connoisseur. The smaller, more personal setting allows for meaningful conversations with the hosts, and the variety of wines ensures you leave with a real appreciation for the region’s diversity. With only 45 minutes here, you’ll have enough time to savor the wines and enjoy the rustic charm.

Return to Florence

By 3:50 PM, it’s time to head back, with a 40-minute drive taking you back to Florence. The tour concludes around 4:30 PM, leaving you plenty of time to continue exploring the city, reflect on your day, or relax at a café.

What’s Included and What to Expect

This experience offers a lot of value for the price. For $242.67 per person, you get:

• Wi-Fi hotspot to stay connected during your trip
• Wine and olive oil tastings at two wineries, plus a third sample at San Michele a Torri
• A generous Tuscan lunch paired with regional wines, cheeses, and salami
• A bottle of Prosecco and bottled water to enjoy during the day
• Pickup and drop-off from select Florence hotels, making logistics seamless
• Comfortable, air-conditioned Mercedes van for smooth travel

Reviewers emphasize the quality of the food and wine, often mentioning the knowledgeable guides who make the experience both fun and educational. Many comments highlight the beautiful scenery and the chance to sample multiple Chianti wines, which is invaluable for anyone wanting to learn about the region’s viticulture.

What’s Not Included

A few travelers note that gratuities are not included, so if you feel your guide provided exceptional service, a tip is appreciated. Also, since the tour is limited to 8 people, it’s essential to book well in advance—most travelers do so around 60 days ahead.

Transportation and Group Size

The small group of up to 8 ensures a more relaxed, intimate atmosphere. The Mercedes van offers a comfortable ride, and the driver/guides are praised for their professionalism and local knowledge. The timing—starting at 8:00 AM and returning around 4:30 PM—strikes a good balance between sightseeing and leisure.

Flexibility & Cancellation

Cancellation is free up to 24 hours before the tour, allowing some flexibility should your plans change. However, keep in mind that poor weather might lead to rescheduling or refunds, so check the forecast.

Authentic Experiences Based on Real Reviews

Many travelers have raved about the guides’ expertise. Names like Claudius, Alberto, Gabrielle, Sara, and Frankie come up repeatedly, with reviews praising their warmth, knowledge, and helpfulness. One reviewer notes that Claudius explained everything clearly and made the experience very convenient. Others loved the personalized attention, especially when only 4 people joined the tour, making the day feel more like visiting friends than a commercial activity.

The wine tastings receive high marks, with travelers describing the properties as stunning and the hosts as friendly and knowledgeable. The lunch, often highlighted as a highlight, features regional specialties served in beautiful settings, paired with some of Italy’s finest wines.

Even the scenic stops garner praise, with visitors noting the breathtaking views of Florence and Tuscany, perfect for photography and just soaking in the atmosphere.

The Sum Up

This semi-private Chianti and San Gimignano tour offers a compelling mix of scenic beauty, authentic wine experiences, and personal service—all at a reasonable price point considering the inclusions. It’s best suited for travelers who want a more intimate alternative to large group tours, with a focus on quality food, wine, and meaningful exploration.

If you’re passionate about wine, love picturesque towns, and appreciate knowledgeable guides, this experience will likely become a highlight of your Florence adventure. The combination of stunning vistas, delicious regional cuisine, and small-group intimacy ensures you can savor Tuscany’s best without feeling rushed or lost in a crowd.

FAQs

Is hotel pickup included? Yes, free pickup and drop-off are offered from select Florence hotels within the historic center. For private residences or B&Bs outside central Florence, the meeting point is in front of Hotel Boccaccio.

How many people are in the group? The tour is limited to a maximum of 8 travelers, ensuring a more personalized experience.

What should I wear? Comfortable clothing and shoes suitable for walking are recommended, especially since you’ll be exploring towns and wineries.

Will I have enough time in San Gimignano? Yes, you’ll have around 1 hour and 25 minutes to explore the medieval town, enjoy gelato, and take photos.

What wines will I taste? You’ll sample Chianti wines at two wineries and additional varieties at San Michele a Torri, gaining a broader understanding of this regional specialty.

Is the lunch included? Yes, a traditional Tuscan lunch with regional dishes and wines is part of the experience, often praised for its quality and authenticity.

Can I cancel if my plans change? Yes, full cancellation is possible up to 24 hours before the tour for a full refund.

Is this tour suitable for all ages? Most travelers can participate, but those sensitive to winding roads or with mobility issues may want to consider the drive’s scenic nature.

This tour combines the best of Tuscany’s landscapes, culinary delights, and history, all wrapped into a relaxed, small-group experience. Whether you’re a wine lover or just want a taste of authentic Tuscany, it’s a day worth savoring.