Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Exploring the Heart of Tuscany: A Deep Dive into the Chianti Wine Tour from Florence to San Gimignano

If you’re dreaming of rolling hills, ancient towns, and some of Italy’s best wines, a private Chianti wine tour from Florence might be just what you need. This full-day experience offers a perfect mix of scenic drives, historic charm, and tasty wine tastings — all in the comfort of a private vehicle. From the moment you start at Piazzale Michelangelo with its panoramic views of Florence, to wandering the enchanting streets of San Gimignano, the tour promises a genuine taste of Tuscany’s timeless beauty.

What we love most about this tour is its combination of intimate guided visits to two different wineries, and the chance to explore San Gimignano’s medieval streets at your own pace. Plus, the option to upgrade and enjoy a delicious Tuscan lunch paired with local wines really enhances the experience. The only potential downside? The tour’s duration means a somewhat packed schedule, but that’s typical for a full-day excursion.

This tour is best suited for travelers who want a balanced mix of scenic sightseeing, wine education, and authentic Tuscan flavor — especially those who appreciate personalized attention and want to avoid the crowds. If you’re curious about Italy’s wine-making process or want a hassle-free way to explore Chianti’s vineyards, this experience could be a perfect fit.

Key Points

• Private, full-day experience offering personalized attention
• Visits to San Gimignano and two wineries in Chianti
• Options to upgrade for lunch and wine tastings
• Hotel pickup and drop-off included for convenience
• Comfortable transportation in a Mercedes-Benz vehicle
• Flexible cancellation policy with full refund if canceled 24 hours in advance

An In-Depth Look at the Chianti Wine Tour

Starting Point: Piazzale Michelangelo

Our journey begins at Piazzale Michelangelo, one of Florence’s most iconic viewpoints. Here, you’re greeted with sweeping views of the city skyline, the Arno River winding through the historic center, and the surrounding hills blanketed in vineyards. It’s a perfect photo op and a serene spot to start your day. Reviewers mention this as a highlight, describing it as a way to set the mood before heading into the Tuscan countryside.

Scenic Drive to San Gimignano

From Florence, you’ll leave behind the hustle and bustle, traveling through gentle rolling hills and vineyards, a sight that immediately transports you to Tuscany’s postcard-perfect landscape. The drive alone is worth the trip, with travelers like Michelle praising the “beautiful views” during their 2-hour ride to San Gimignano.

Exploring San Gimignano

Once in San Gimignano, the experience shifts to wandering through a medieval marvel. Its walls, narrow cobblestone streets, and towers create a fairy-tale setting that enchants every visitor. Reviewers highlight Gino’s personable and knowledgeable guidance, sharing that “Gino was a wealth of local insights,” making the visit more than just a walk through an old town — it’s a journey into Tuscany’s history.

Wine Tasting at Farm Sant’Appiano

Next comes the first winery visit at Farm Sant’Appiano, where you get to see the wine production process firsthand. The focus here is on education — learn how local wines are crafted, from grape to bottle. The tasting experience costs €30 per person, and many guests opt to also enjoy a lunch with wine pairing for around €50-60, which reviewers say significantly enhances the experience.

One guest, Lena, appreciated that “the wineries were quite nice and the tastings were great,” noting the quality of the wines and the friendly staff. The winery’s atmosphere, coupled with insights from the guides, makes this stop especially valuable for wine enthusiasts.

Exploring Chianti Vineyards

The journey continues on the Chianti road (Strada Statale 222 Chiantigiana), a stretch famous for its stunning vistas of vineyards, cypress trees, and rolling hills. Traveling along this scenic route, you’ll see why Chianti is world-renowned for its wines.

At the second winery, the focus is on getting up close with the winemaking process. The tasting here also costs €30, with the option to upgrade to include a meal. Reviewers note the wines are “exquisite,” and the opportunity to see the vineyards up close adds to the sense of authenticity.

Return to Florence

After a full day of sightseeing and tasting, your driver will take you back, driving along the Chiantigiana, which many describe as one of the most beautiful roads in Tuscany. The 45-minute drive is full of spectacular views, making it a fitting end to your adventure.

Practicalities and Comfort

Throughout the day, the group remains private, with a Mercedes-Benz vehicle providing comfort and air-conditioning. WiFi on board and bottled water keep you refreshed, while the timing ensures you’re not rushing through each stop. Many reviewers, including Brandon, appreciated the professional guides like Gino, who shared stories and insights that made the experience both educational and entertaining.

Cost-Value Analysis

With a starting price of just over $300 per person, this tour offers significant value considering the all-inclusive transport, the private nature, and the guided visits. The option to upgrade for lunch and tastings makes it customizable, catering to those who want a more indulgent experience.

While wine tastings are not included in the basic fee, the €30 charge per tasting is reasonable and grants access to high-quality wines. Many guests felt that the overall experience, including the scenic drives, expert guides, and charming stops, justified the cost.

Who Should Consider This Tour?

This tour is ideal for travelers who want a personalized, in-depth introduction to Tuscany’s wine and medieval towns without the hassle of organizing multiple visits themselves. It’s perfect for couples, small groups, or solo travelers who appreciate comfort and expert guidance.

Wine lovers will especially enjoy the chance to taste exquisite Chianti wines and learn about winemaking. History buffs will appreciate the stop in San Gimignano, while those looking for scenic beauty will love the breathtaking landscapes along the route.

Final Thoughts: Is It Worth It?

In terms of value, this private Chianti tour checks most boxes. The combination of beautiful scenery, authentic wine visits, and expert guides makes it stand out among Tuscany excursions. The flexibility to upgrade for meals and tastings allows each guest to tailor their experience.

Travelers who want a stress-free day with a personal touch will find this tour a memorable way to explore Tuscany’s highlights. Whether you’re celebrating a special occasion, seeking a relaxing escape, or simply looking to indulge your senses, this experience offers a well-rounded and immersive taste of Italy’s wine country.

FAQs

What is included in the tour price?
The tour includes private transportation in an air-conditioned vehicle, all fees and taxes, bottled water, WiFi onboard, and pickup/drop-off at your hotel.

Are wine tastings included in the price?
No, wine tastings are €30 per person at each winery, and can be paid directly during the stops. You can also upgrade to enjoy a full lunch with wine for around €50-60.

Can I cancel the tour?
Yes, you can cancel free of charge up to 24 hours before the scheduled start time, receiving a full refund.

Is this tour suitable for all ages?
It’s mainly designed for adults over 18 due to wine tastings. The tour’s timing and activity level suit most travelers, but check with the provider if you have specific needs.

How long is the drive from Florence to San Gimignano?
Approximately 2 hours. The scenic drive is part of the enjoyment, with many guests remarking on the lovely views along the way.

Is lunch included?
Lunch is optional and can be added on the day for an extra cost. The tour price does not include lunch unless you choose the upgrade.

What guides will be with us?
A professional driver, often knowledgeable about local history and wine, will accompany you. Reviewers mention guides like Gino and Luigi, who are praised for their friendliness and expertise.

Can I customize the experience?
The tour is private, so you can discuss preferences with your guide, and upgrades for meals and tastings are available.

In essence, this private Chianti wine tour from Florence offers an ideal mix of stunning scenery, authentic wine experiences, and personal guidance — perfect for those who want to truly savor Tuscany without the crowds or complications.