Florence: Private Tuscany Wine Tour with San Gimignano

If you’re craving a taste of Tuscany’s renowned wine scene combined with a charming medieval town experience, this private tour offers a well-rounded day out. With a comfortable minivan, expert guides, and a small group feel, it promises both education and relaxation. While the price might seem steep at over $400 per person, the included visits, tastings, and authentic Tuscan lunch make it a solid value for those eager to dive into the region’s viticultural delights.

What really shines are the intimate visits to two distinguished wineries, the chance to learn about wine-making, and the opportunity to explore San Gimignano at your leisure. However, controlling a full day’s schedule with a fixed itinerary means limited flexibility, so it’s best suited for travelers who like planned experiences and are ready for a full day of sightseeing.

This tour is perfect for wine lovers, history enthusiasts, and those wanting a taste of authentic Tuscany without the hassle of self-driving. If you’re after a personalized, guided experience with plenty of tastings and cultural exploration, this is worth considering.

Good To Know

Private Experience: Small group or private tour ensures personalized attention.
Wine Focus: Visit 2 renowned wineries and enjoy tastings of Chianti Classico and Vernaccia.
Authentic Meal: Full Tuscan lunch with wine pairings enhances the tasting experience.
Cultural Stop: Free time in San Gimignano allows for sightseeing, shopping, and gelato.
Educational Aspect: Guided visits and tastings help you understand wine production and regional varieties.
Convenient Transport: Comfortable minivan with pickup at a central Florence meeting point.

You can check if your dates are available here:

Exploring the Itinerary and What You Can Expect

Starting Point and Ease of Access

The tour begins at Piazza della Calza near Porta Romana, a convenient city-center meeting spot in Florence. The guide, who is bilingual in English and Italian, greets you with enthusiasm, ready to kick off what promises to be a full day. The minivan, accommodating up to eight guests, is a cozy yet comfortable way to explore the beautiful Tuscan countryside without the worries of driving yourself.

Most reviews note that the pickup is smooth, and the guide is friendly and knowledgeable — a key factor in setting the tone for the day. Expect the first hour of travel to be scenic as you leave the city behind and start ascending into Tuscany’s rolling hills.

First Winery Visit: Chianti’s Hidden Gems

The first stop takes about an hour, giving you time to enjoy the scenic drive through the Chianti hills. Once at the first winery, you’ll partake in a guided tour of the vineyards and cellars. Here, guests have learned that “the guide shared both technical details and fun anecdotes about wine-making,” which helped make the experience both educational and engaging.

You will taste a selection of local wines, including Chianti Classico, which is the region’s most iconic red. Some guests mention they appreciated the opportunity to learn how to discern different flavors, which “felt like a small wine class.” Extra virgin olive oil tasting is also included, offering a taste of Tuscany’s other famous product.

Moving on to the Second Winery: Lunch and More Tasting

Next, you’ll hop back into the van and head to a second winery, set against the backdrop of the famous San Gimignano towers. Here, the experience deepens: a guided tour of the vineyards and cellars, coupled with tastings of various wines. The highlight for many is the full Tuscan lunch with carefully curated wine pairings.

Guests frequently comment that “the meal was authentic and generous,” with some mentioning the wine pairing elevates everything. It’s a great moment to relax, enjoy the flavors, and ask questions about regional wine and food traditions.

More Great Thing To Do Nearby

San Gimignano: Medieval Charm at Your Pace

Most of the group’s free time in San Gimignano lasts around 1.5 hours, giving plenty of opportunity to wander the narrow streets, shop in boutique stores, or indulge in a scoop of gelato from the town’s renowned gelateria — often called a world-champion spot. The views of the countryside from the town’s vantage points are stunning, and many visitors say that “the medieval towers make for perfect photos.”

While guided tours aren’t included here, plenty of reviews mention that the town’s charm and scenic vistas are worth every minute of wandering. The free time allows for a relaxed exploration, as opposed to rushing through sights.

Return Journey

After your time in San Gimignano, the van heads back toward Florence, with a brief stop in the Chianti area for scenic views. The return journey typically lasts about an hour, giving you time to unwind and reflect on the day’s experiences. Most guests appreciate the comfortable transport and the fact that the tour ends right back where it started, at the same Florence meeting point.

What Makes This Tour Stand Out

Personalized and Small Group Experience

The private nature of this tour means you’re not just another face in a large bus. Guests consistently mention how the guide’s insights made the experience more meaningful, offering a deeper understanding of Tuscan wines and culture. The small group size fosters a relaxed atmosphere, perfect for asking questions and engaging with the guide.

Focus on Authentic Wine and Food

Unlike generic tours, this experience emphasizes regional wines like Chianti Classico and Vernaccia, giving you a real taste of Tuscany’s viticultural identity. The inclusion of a full Tuscan lunch paired with wine adds significant value, allowing for a true culinary experience rather than just tastings.

Well-Accompanied Scenic Drive

The drive through Chianti and towards San Gimignano isn’t just transportation — it’s part of the experience. The guide points out landmarks and shares stories that animate the landscape, making the journey as enjoyable as the stops.

Authentic Town Exploration

San Gimignano’s medieval streets are a highlight, offering a glimpse into Italy’s past. Guests have loved wandering freely, shopping for local products, or simply soaking in the atmospheric views, which are often described as ” postcard-perfect.”

The Practical Side: What You Should Know

Duration and Timing

The 7-hour itinerary is well-paced but can be considered full. Starting at 9:45 am, this tour ends around 5 pm, making it suitable for those with a full day to dedicate. Check availability to confirm starting times, as they may vary.

Cost and Value

At $402.29 per person, this tour might seem pricey, but it includes everything from private transport, guided wine visits, tastings, a full meal, and town exploration. For wine lovers and those eager for a curated experience, the cost aligns with the value.

Accessibility and Limitations

This tour isn’t suitable for pregnant women or wheelchair users, primarily due to the nature of winery visits and walking through medieval streets. It’s a good choice for those comfortable in a small group and on their feet.

Flexibility and Customization

The itinerary is described as customizable, so if you have specific preferences or dietary needs, it’s worth mentioning in advance. Most reviews indicate the guide was accommodating to special requests.

Booking and Cancellation

Flexible booking options are available — cancel up to 24 hours in advance for a full refund. This makes planning less stressful, especially for spontaneous travelers.

Final Thoughts

This private Tuscany wine tour from Florence offers a comprehensive look into the region’s best-known wines, rich culture, and scenic towns. It’s a well-rounded experience that combines education, indulgence, and leisure, all within a small-group setting that feels personalized.

Ideal for wine aficionados, history buffs, and food lovers, the tour ensures you’ll leave with a deeper appreciation of Tuscany’s culinary and cultural traditions. The included lunch and the opportunity to wander San Gimignano’s historic streets elevate the experience beyond just wine tasting.

While the price isn’t pocket change, the quality of the visits, guide expertise, and authentic cuisine make it a worthwhile splurge for those wanting a memorable day in Tuscany. If you’re comfortable with a full schedule and eager to learn about regional wines while soaking in picturesque landscapes, this tour hits all the right notes.

FAQ

Is transportation included?
Yes, transportation in a comfortable 8-seat minivan is included from Florence to the wineries and San Gimignano.

Where does the tour start and end?
It starts at Piazza della Calza near Porta Romana in Florence at around 9:45 am and returns to the same point by 5 pm.

Are meals included?
Yes, a full Tuscan lunch with wine pairings at the second winery is part of the package.

Can I customize the itinerary?
The itinerary is described as customizable, so you should inform the tour provider of any preferences or dietary needs.

Is this tour suitable for children or pregnant women?
No, it’s not recommended for pregnant women or those in wheelchairs due to winery visits and walking in historic streets.

What types of wines will I taste?
You will sample local varieties including Chianti Classico and Vernaccia, with tastings of extra virgin olive oil included.

Is there free time during the town visit?
Yes, you’ll have approximately 1.5 hours in San Gimignano for sightseeing, shopping, and enjoying gelato at the acclaimed gelateria.

This tour blends the best of Tuscan wine, cuisine, and medieval charm into one memorable day — perfect for those wanting a guided, authentic experience without rushing.

You can check if your dates are available here: