Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Introduction to the Chianti Wine Tour from Florence

This highly-rated private wine tour offers a flavorful slice of Tuscany’s countryside, perfect for those who want a well-rounded, authentic experience without the hassle. Starting at Piazzale Michelangelo, you’ll enjoy sweeping views of Florence before heading out into the rolling hills of Chianti. The day then unfolds with a visit to the medieval town of San Gimignano—famous for its towers—and two carefully selected wineries, all accompanied by a knowledgeable driver and the comfort of an air-conditioned Mercedes-Benz.

What I find particularly appealing about this experience is its thoughtfully balanced mix of scenic beauty, historical charm, and wine education. The fact that you can upgrade to include lunch and tastings makes it flexible depending on your budget and appetite for local flavors. The reviews consistently praise the guides—especially Luigi and Gino—for their friendliness and expertise, which can turn a good tour into an unforgettable one.

One point to consider is that wine tastings are not included in the base price, so if you’re keen on sampling various Chianti wines, you’ll want to budget an extra $30 per winery. Also, because it’s a private tour, expect a more personalized and less hurried pace—great for those who prefer a tailored experience over larger group tours.

Key Points

• Personalized Experience: Private transportation with a knowledgeable, friendly guide ensures a relaxed, customized day.
• Stunning Views & Authentic Towns: Panoramic vistas from Piazzale Michelangelo and medieval charm in San Gimignano make for inspiring stops.
• Flexible Options: You can opt to include a delicious Tuscan lunch and multiple wine tastings, elevating the experience.
• Expert Guides: Testimonials highlight guides like Luigi and Gino, who bring warmth and insight to the day.
• Value for Money: The cost reflects not only the transport but also the curated visits, making it a worthwhile splurge for wine lovers.
• Ideal for Couples & Small Groups: The private setup suits those seeking intimacy, personalized attention, and a more exclusive experience.

Exploring the Itinerary in Detail

Starting at Piazzale Michelangelo

Your day kicks off at Piazzale Michelangelo, famous for its sweeping views over Florence. It’s the perfect spot to get those classic photos of the city skyline, with the Arno River weaving through the buildings. Starting early gives you a quiet moment before the day’s adventures, and from here, your driver takes over. The 15-minute stop offers no ticket costs, but the views alone are priceless—a reminder of Tuscany’s landscape that you’ll carry home long after.

The Charm of San Gimignano

Next, the tour ventures into the medieval streets of San Gimignano—a town that looks like it’s straight out of a storybook. Its towers and walls have stood for centuries, offering a palpable sense of history. Expect to spend about two hours here, enough time to stroll narrow streets, take panoramic photos, and enjoy the town at a relaxed pace. Reviewers love this stop, noting guides like Gino are personable and knowledgeable about the town’s history and architecture. Michelle describes Gino as a “wealth of knowledge,” and it shows in how well he weaves stories about the town’s towers and past into the tour.

The wineries of Chianti

The core of the day is visiting two wineries in Chianti. While the specifics may vary depending on availability, the stops typically include Farm Sant’Appiano and a second vineyard along the Chiantigiana road. These visits are where the tour truly shines because you get to see vineyards up close, learn the secrets of winemaking, and, for an extra fee, sample seven different wines. The reviews are glowing—“The wineries were amazing,” says Lena, highlighting how enjoyable and informative the tastings are.

The price for wine tasting is about $30 per person, but if you choose to add lunch, it’s around $50–$60, and many find the quality of the food and the wines well worth it. It’s an opportunity to experience authentic Tuscan wines and local cuisine in a relaxed setting, often with the chance to chat with winemakers and learn their craft.

Scenic Drive & Return to Florence

The return leg along Strada Statale 222 Chiantigiana offers some of the most breathtaking views of vineyards, olive groves, and rolling hills. It’s a slow drive through some of Italy’s most iconic landscapes, so don’t forget your camera. The whole trip lasts approximately 7 to 8 hours, giving you enough time to savor each stop without feeling rushed.

Why This Tour Excels

Guides Who Make It Special

Multiple reviews praise the knowledge and kindness of the guides, especially highlighting Luigi and Gino. It’s clear that their warmth enhances the experience, making each stop more than just a sightseeing point—they add context, stories, and genuine friendliness. “Luigi was the best tour guide,” shares Michelle, emphasizing how his insights made the wine tastings and towns come alive.

Comfortable & Private Transport

Travel is in a luxurious Mercedes-Benz vehicle, which keeps the ride comfortable and smooth. With air conditioning and WiFi onboard, you can relax, stay connected, or take photos during the drive. The private nature of the tour means your group gets undivided attention and a flexible schedule—perfect for couples or small groups who prefer tailored experiences.

Authentic & Relaxed Experience

This isn’t a quick bus tour with dozens of strangers. Instead, you get a personalized, relaxed day that balances sightseeing, tasting, and wandering. The inclusion of San Gimignano’s medieval charm adds a cultural layer that complements the wine experience beautifully. Also, the option to decide on the day whether you want to add lunch or more tastings provides flexibility.

What Could Be Better

While the tour is excellent overall, a consideration is the additional cost for wine tastings and lunch. Since these are not included in the base price of $319, your final expenses could increase if you indulge in multiple tastings and a hearty meal. Planning ahead helps manage expectations. Also, for those with limited time, the 8-hour duration might be long, but it’s well-spent if you’re eager for a comprehensive taste of Tuscany.

Who Will Love This Tour

This experience is ideal for wine lovers who want a curated, intimate introduction to Chianti wines. Couples looking for a romantic day of sightseeing and tasting will find it especially appealing, as well as small groups wanting personalized attention. History buffs will enjoy San Gimignano’s medieval charm, while anyone who appreciates stunning landscape views will be captivated during the drive.

It’s best suited for travelers who value comfort, informative guides, and the flexibility to customize their experience with optional lunch and tastings. If you’re ready to explore Tuscany beyond Florence’s city limits at a relaxed pace, this tour hits all the right notes.

FAQs

Is transportation included?
Yes, the tour includes private transportation in an air-conditioned Mercedes-Benz vehicle, with hotel pickup and drop-off in Florence.

Can I cancel the tour?
Absolutely. You can cancel up to 24 hours in advance for a full refund, making it a risk-free option if your plans change.

Are wine tastings included?
No, wine tastings cost about $30 per person at each winery but can be added on the day if you wish. Lunch is optional and costs around $50–$60.

How long does the tour last?
The entire experience takes approximately 7 to 8 hours, from Piazzale Michelangelo in the morning to returning to Florence.

What is the group size?
This is a private tour, so only your group will participate, which means more personalized service.

Are children allowed?
While not explicitly stated, most travelers of most ages can participate, but those under 18 should note that wine tastings are not for minors.

What should I bring?
Bring comfortable shoes for walking in San Gimignano, a camera for scenic views, sunscreen, and an appetite for delicious Tuscany wines and food options.

Is lunch included?
No, lunch is optional. If you want it, expect an additional fee of around $50–$60, which also includes wine tastings.

To sum it up, this private Chianti wine tour from Florence offers a thoughtfully curated, intimate taste of Tuscany’s cultural and vinicultural gems. The guides’ warmth and expertise help turn a sightseeing trip into an engaging, delicious adventure. It’s perfect for those who want a flexible, personalized experience with stunning scenery, authentic towns, and quality wines. If your idea of a perfect day includes indulging in local flavors, learning from passionate guides, and soaking in breathtaking views, this tour will certainly satisfy your cravings.