From Florence: Semi Private Deep Wine Chianti San Gimignano

An Intimate Journey Through Tuscany’s Wine and Medieval Towns

This semi-private day trip from Florence offers a deep dive into the heart of Tuscany, combining scenic landscapes, top-quality wines, and historic towns. Priced affordably with the option to reserve now and pay later, it provides a relaxed pace that includes visits to two wineries, a full Tuscan lunch, and a stop in the iconic San Gimignano. With a small group limit of only 8 participants, the experience feels personalized, guided by knowledgeable English-speaking guides who make the journey both informative and warm.

The tour’s highlights include tasting a variety of Chianti wines at a family-run estate, learning about the region’s viticulture, and exploring San Gimignano’s medieval towers. It’s a perfect choice for those eager to enjoy local flavors, stunning Tuscan views, and historic charm all in one day. The tour is designed to balance sightseeing, wine tasting, and leisure, making it ideal for wine lovers and history enthusiasts alike.

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Key Points

• Small group size ensures a personalized experience with a maximum of 8 participants.
• Visits to two wineries, including a family-run estate in San Michele a Torri, with guided wine tastings.
• Includes a full Tuscan lunch with local cheese, salami, and olive oil, paired with regional wines.
• Stops at Piazzale Michelangelo for stunning panoramic views of Florence.
• Exploration of San Gimignano’s historic towers and streets, with a guide explaining its history.
• Total duration of 9 hours with well-paced visits and scenic drives.

Scenic Drive to Piazzale Michelangelo with City Views

The tour starts with a 15-minute drive from Florence to Piazzale Michelangelo. This large square offers commanding views of Florence, with a bronze replica of Michelangelo’s David serving as a striking centerpiece. The photo stop here provides a perfect introduction to the region’s beauty, with sweeping vistas of the city’s rooftops, domes, and the Arno River.

This moment allows time to appreciate the Tuscany landscape from above before heading further into the countryside. The scenic drive that follows transports guests into the rolling hills that define the Chianti region, setting the tone for the day ahead.

Exploring the Medieval Charm of San Gimignano

After about an hour’s drive, the group reaches San Gimignano, renowned for its medieval towers and well-preserved city walls. A self-guided tour allows visitors to stroll through its charming streets, shop for local crafts, and admire the city’s imposing towers that have earned it the nickname “Medieval Manhattan.”

The guide shares insights into the town’s history, highlighting its importance as a trading hub in medieval times. The scenic views en route to San Gimignano make this stop especially picturesque, and the roughly 80-minute visit gives plenty of time for photos and exploration.

Tasting at a Family-Run San Michele a Torri Winery

Next, the journey continues with a 50-minute drive to a typical Tuscan farmhouse in the Chianti area. Here, the focus is on wine tasting at a family-owned winery in San Michele a Torri. Visitors enjoy sampling a variety of Chianti wines, discovering the nuances of each vintage.

The winery experience includes insights into local winemaking traditions and the opportunity to try other excellent Chianti wines. This stop is especially appreciated for its authentic atmosphere and the chance to learn about the region’s wine culture directly from the producers.

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Indulging in a Full Tuscan Lunch with Local Flavors

Following the wine tasting, guests are treated to a delicious Tuscan lunch at the farmhouse. The meal features local specialties, including cheese, salami, and olive oil, paired with wines from the estate. The lunch and wine pairing lasts approximately 2 hours and 15 minutes, providing a relaxed setting to savor the flavors and enjoy the countryside views.

This meal exemplifies the culinary richness of Tuscany, with the chance to appreciate the region’s food and wine traditions in a welcoming environment. The scenic Chianti hills serve as a stunning backdrop during lunch, enhancing the experience.

Visiting the Chianti Hills Wineries for a Second Tasting

After lunch, the tour continues with a 45-minute drive to another Chianti winery in the hills. This visit involves a guided tour of the estate and a second wine tasting, offering an opportunity to compare different vineyards and winemaking styles.

Guests learn about the winery’s history and techniques, and get to enjoy more regional wines. This second tasting lasts about 70 minutes, giving ample time to appreciate the complexity of Chianti wines and ask questions directly to the guides.

Scenic Return and Drop-Off at Central Florence Hotels

The day concludes with a 40-minute drive back to Florence, dropping guests off at either Hotel Boccaccio or Hotel Davanzati. The transfer offers one last chance to enjoy the rolling Tuscan landscape and reflect on the day’s highlights.

The tour’s timings are well-managed to ensure a comfortable pace, and the pickup is straightforward — guests need only arrive 10 minutes early and look for the black van with the Truescany logo.

The Guide and Overall Experience

The guides are praised for being knowledgeable and friendly, with reviews highlighting the personalized attention and ability to adapt the trip to the group’s interests. One guide, Alberto, is noted for his wealth of knowledge and engaging style, while Francisco is appreciated for his humor and explanations, even in rainy weather.

The tour’s small group size ensures a more intimate atmosphere, allowing for meaningful interactions and a relaxed pace. The inclusion of audio guides in English helps enhance understanding, especially during the walking parts of the town visit.

Practical Details and Booking Flexibility

This tour is designed for comfort and convenience. Comfortable shoes are recommended for walking around towns and wineries, and large luggage is not allowed, making it suitable for most travelers. The full-day experience lasts 9 hours, with flexible starting times available.

Booking is flexible with the option to cancel up to 24 hours in advance for a full refund, and the reserve now, pay later policy helps travelers plan with confidence. Pickup locations are easy to access, with meeting points at Hotel Boccaccio or Hotel Davanzati.

Authenticity and Personalization in Every Stop

The family-run wineries and the guided visits focus on regional authenticity, offering genuine insights into Tuscany’s wine-making traditions. The lunch emphasizes local ingredients, and the stops in San Gimignano and the Chianti hills showcase the area’s rich history and stunning natural beauty.

The itinerary strikes a good balance between structured visits and leisure time, making it ideal for those who want to enjoy a comprehensive taste of Tuscany without feeling rushed.

Who Will Most Appreciate This Tour?

This experience works best for wine lovers, history enthusiasts, and anyone seeking a personalized way to discover Tuscany’s landscapes and towns. The small-group format makes it especially appealing for travelers who prefer a more intimate, engaging setting.

While the tour is well-paced, those sensitive to walking or driving may want to consider their comfort level with the various stops. The delicious food, stunning views, and knowledgeable guides make it a worthwhile choice for a memorable day in Tuscany.

Frequently Asked Questions

Is this tour suitable for small groups?
Yes, the tour is limited to 8 participants, ensuring a more personalized experience.

What is included in the wine tastings?
Guests taste a variety of Chianti wines at two different wineries, including a family-run estate and a second vineyard in the Chianti hills.

How long is the lunch?
The full Tuscan lunch lasts around 2 hours and 15 minutes, featuring local cheese, salami, and olive oil paired with regional wines.

Are the pickup and drop-off locations convenient?
Yes, guests are picked up and dropped off at Hotel Boccaccio or Hotel Davanzati, both central Florence locations.

What should I bring?
Comfortable shoes are recommended for walking around towns and wineries.

Can I cancel this tour?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility for planning.

You can check availability for your dates here: More Great Tours Nearby