Private Tour in San Gimignano and Chianti Day Trip from Florence

A Day in Tuscany: Private Tour to San Gimignano and Chianti from Florence

If you’re craving a taste of Tuscany’s timeless charm, this private day trip from Florence offers a well-rounded experience of medieval towns, scenic vineyards, and delicious food. Costing around $197.38 per person, and lasting roughly 8 hours, this tour includes stops at San Gimignano, Monteriggioni, a family-run winery, and Greve in Chianti. With a personalized touch, your guide Gino (who gets glowing reviews) will help bring the region to life with stories, tastings, and a genuine appreciation for the local way of life.

What we love most? First, the chance to stroll San Gimignano, the “Medieval Manhattan,” with its iconic towers and unforgettable gelato. Second, the intimate visit to a family-owned vineyard where you’ll enjoy authentic wine and olive oil — a real taste of Tuscany’s soul. The only caveat? The day moves quickly, so be prepared for a full itinerary, especially if you want to linger in each village.

This trip suits history buffs, wine lovers, or anyone eager to experience Tuscany beyond Florence. It’s particularly perfect for those who appreciate small-group tours that allow for flexibility and personalized attention.

Key Points

• Authentic Experiences: Visit historic towns, local wineries, and family-run shops, gaining genuine insight into Tuscan life.
• Comfort & Convenience: Air-conditioned transport and private group setting make for a relaxed day.
• Scenic Beauty: Enjoy immersive views of rolling vineyards, medieval walls, and charming squares.
• Flexible Schedule: While packed, the itinerary balances guided visits with free time, perfect for your personal pace.
• Expert Guidance: Gino’s knowledge enriches the experience, sharing stories and recommendations.
• Value for Money: For less than $200, you get a full day of sightseeing, tastings, and authentic local encounters.

A Deep Dive into the Experience

The tour starts at 9:30 am in Florence, with a comfortable ride to your first stop—San Gimignano. Known as the “Medieval Manhattan,” this UNESCO World Heritage site offers a walk through narrow cobblestone streets lined with towers that once signified wealth and power. The highlight? A chance to sample what many consider the best gelato in the world. It’s a small window of time—about two hours—but enough to savor the atmosphere and indulge in a scoop of creamy, artisan ice cream. One reviewer described it as “the best gelato ever,” which speaks volumes about the quality here.

Next, you’ll visit Monteriggioni, a beautifully preserved medieval fortress town with original walls that still surround the village. It’s a short 20-minute drive and offers a glimpse into Tuscany’s strategic past. Expect about 20 minutes here, enough for photos and a quick wander along the ancient ramparts. It’s a picturesque spot that transports you back centuries, ideal for history lovers and photography enthusiasts alike.

The heart of the tour lies at Poggio Amorelli, a family-run vineyard and olive oil producer. Here, the focus is on small-group, personalized experiences. You’ll tour the estate, learn about the production process, and indulge in a lunch paired with local wines. The guide’s careful planning shines through — you’ll get to sip wines that reflect the region’s best, while enjoying a homemade meal in the midst of rolling vineyards. The reviews highlight how much guests appreciated the “creative, lively itineraries” and the “careful planning” that ensured everyone enjoyed every moment.

Finally, the journey wraps up at Greve in Chianti, a charming medieval village with a lively square and a famous butcher shop, Falorni. This shop is renowned for its high-quality meats and traditional Tuscan delicacies. A 30-minute drive back to Florence concludes the day, giving you just enough time to reflect on the day’s discoveries. The last leg includes some free time, so you can browse shops or relax in the piazza.

Transport and Group Size

The use of an air-conditioned vehicle ensures comfort throughout the day, especially important in warmer months. The tour is private, which means only your group participates, allowing for a more tailored experience. While the exact group size isn’t specified, the focus on personalized attention and expert guides suggests a small, manageable group—perfect for those who dislike the feeling of being just another tourist.

Cost and Value

At $197.38 per person, this tour offers a lot—visiting multiple towns, wine tastings, and a scenic drive—making it a good value for a full-day, immersive experience. The inclusion of admission-free stops (like San Gimignano and Monteriggioni) helps keep costs transparent, focusing on the experience rather than hidden fees.

Authenticity and Personal Touch

Guests consistently praise Gino and other guides for their knowledgeable, friendly manner and ability to bring the region’s history and culture alive. As one reviewer noted, “Gino was wonderful,” emphasizing the value of a passionate guide. The carefully curated stops ensure you taste the real Tuscany, not just tourist traps.

Who Should Consider This Tour?

This experience is ideal for travelers who want a personalized, relaxing day outside Florence, with a focus on history, food, and wine. It suits those who appreciate small-group settings for more meaningful interactions. If you’re eager to see iconic sights like San Gimignano and get insider access to a family-run vineyard, this tour delivers. It also fits well for those who value authentic local foods and wines over commercialized experiences.

While the day is busy, the pacing allows for plenty of photo opportunities and free time to soak in the atmosphere. If you’re traveling with family, friends, or as a couple seeking a memorable day in Tuscany, this trip balances guided storytelling with personal exploration.

The Sum Up: Is This Tour Worth It?

In a nutshell, this private day trip offers a well-rounded taste of Tuscany’s best—medieval towns, vineyards, and authentic flavors—all wrapped in the comfort of private transportation and expert guidance. For around $200, you gain access to a carefully curated itinerary that highlights top sights and local treasures.

If your goal is to experience Tuscany’s history, scenery, and culinary delights without the hassle of planning, this trip provides excellent value and a chance for genuine, memorable moments. The flexibility within the schedule, combined with the warmth and knowledge of guides like Gino, makes it a standout choice for those eager to explore Tuscany’s heart.

This tour is perfect for travelers who want an authentic, comfortable, and insightful glimpse into Italy’s most charming region—without the crowds or the rush. It’s a wonderful way to deepen your appreciation of Tuscany’s landscape, food, and ancient towns—all in one memorable day.

FAQ

What is the start time for the tour?
The tour begins at 9:30 am in Florence.

How long does the entire trip last?
It is approximately 8 hours, including travel time, sightseeing, and free moments.

Is transportation provided?
Yes, an air-conditioned vehicle is included for all parts of the trip.

Can I cancel the tour?
Yes, there is free cancellation available up to 24 hours in advance for a full refund.

Is this a group tour or private?
It’s a private tour, meaning only your group participates, ensuring a more personalized experience.

Are meals included?
Lunch is not included but is enjoyed at Poggio Amorelli, where wine tastings and a meal are part of the experience.

Are there any additional costs?
Tips and any extra purchases (like souvenirs) are not included. Admission fees for San Gimignano and Monteriggioni are free.

Who is the tour provider?
Continental Tuscany operates this experience, with expert guides and a focus on authentic Tuscan encounters.

Is this suitable for families?
Yes, the tour’s pace and sights make it family-friendly, especially with the engaging stops and scenic views.

This private Tuscany day trip from Florence balances scenic beauty, history, and culinary delights in a way that leaves travelers with genuine memories. Whether it’s your first visit or your tenth time in Italy, you’ll find this tour a well-crafted way to experience the soul of Tuscany.