Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Experience the Best of Tuscany with a Private Chianti Wine Tour from Florence

A full-day journey that takes you from the bustling streets of Florence to the peaceful rolling hills of Chianti, this private tour offers a taste of Tuscany’s best. For $319.30 per person, you’ll spend around 7 to 8 hours exploring medieval San Gimignano, visiting two carefully selected wineries, and enjoying panoramic views across vineyards and historic towns. The tour begins with a pickup from your Florence accommodation in a comfortable Mercedes-Benz vehicle, making the entire experience seamless and stress-free.

What we love most about this tour: First, the personalized attention you get in a private setting, which means you can tailor your experience—whether it’s more time in San Gimignano or extra wine tastings. Second, the expert guides, who are not just drivers but sources of local knowledge, making every stop more meaningful. A minor consideration might be the cost if you’re on a tight budget, but when you factor in the private transport, exclusive visits, and the potential for an optional delicious lunch, the value quickly adds up.

This tour suits travelers who want an in-depth, authentic experience of Tuscany’s wine country, combined with cultural highlights like San Gimignano’s iconic towers. Perfect for those who appreciate good wine, stunning scenery, and personalized service, especially if you prefer avoiding large group tours.

Key Points

• Private, personalized experience tailored to your pace and interests
• Visit San Gimignano, a medieval jewel with unique towers and scenic views
• Explore two Chianti wineries, learning from local wine producers
• Optional lunch and wine tasting available for extra indulgence
• Comfortable, air-conditioned Mercedes-Benz transport with WiFi
• Ideal for those seeking an intimate, authentic Tuscan experience

An In-Depth Look at the Chianti Wine Tour from Florence

Starting Point: Piazzale Michelangelo

Your day begins at the Piazzale Michelangelo, one of Florence’s most famous lookout points. Here, you can snap photos of the city skyline and the majestic Arno River before heading into the countryside. It’s a great way to set the scene for the day, with panoramic views that hint at the beauty ahead. The meeting point is easy to find, and the tour operator provides a smooth start, setting the tone with their professional service.

Exploring San Gimignano: A Medieval Masterpiece

After a relaxed drive through tuscan hills, you arrive at San Gimignano, often called the “Town of Fine Towers.” This medieval village has a compact, walkable layout with ancient walls, narrow cobblestone streets, and towers that historically served as symbols of wealth and power. Expect about two hours here—ample time to wander, take photos, and soak in the atmosphere.

Travelers consistently praise the guide’s knowledge about San Gimignano’s history and architecture—one review mentions that Gino, the guide, is “very personable and knowledgeable.” Some visitors use this time to enjoy a gelato or explore local artisan shops, all while taking in views of the surrounding vineyards and olive groves. It’s an authentic slice of Italian history, far removed from tourist traps.

First Winery Visit: Farm Sant’Appiano

Next, you’ll visit Farm Sant’Appiano, where you’ll tour the cellars and see firsthand how Tuscan wines are produced. This stop is more than just tasting; it’s an educational experience that reveals the craftsmanship behind the wines. Depending on availability, the winery may vary, but the focus remains on quality and authenticity.

You’ll have the option to enjoy a wine tasting session at this point. The price is €30 per person, which covers tasting several wines directly from the producer’s cellar. For those interested in a more indulgent experience, an optional lunch with seven wines can be added for €50–€60. This allows you to savor local flavors paired with the wines, adding a culinary dimension to your day.

Second Winery: Exploring Chianti’s Vineyards

Following the first winery, you’ll head to another Chianti region’s winery to see vineyards up close and learn about the winemaking process. The drive along the famous Strada Statale 222 Chiantigiana offers breathtaking views—rolling hills dotted with vineyards, cypress trees, and rustic farmhouses. This stretch alone is worth the trip, with many travelers commenting on the “breathtaking” scenery.

At this winery, you’ll again have an opportunity to taste Chianti wines—another €30 for the tasting, with the lunch option available for €50-€60. Many reviews highlight the quality of wines and the personable guides, who provide insights into the regional differences between wines produced here.

Return to Florence with Scenic Vistas

After a leisurely exploration of vineyards and perhaps some last tasting, your driver will take you back to Florence along the Chianti wine road. This scenic route provides perfect photo opportunities and a relaxed way to end the day, with views of vineyards stretching to the horizon. The drive lasts about 45 minutes and is a fitting conclusion to a day of sensory delights.

What Makes This Tour Stand Out

Authentic learning and tasting experiences are at the core of this private tour. Unlike larger groups, you’ll get personalized attention from guides like Gino or Luigi, who are praised for their knowledge and kindness. Several reviews mention that guides made the experience “unforgettable,” sharing stories and insights that enrich the tastings and sightseeing.

The flexibility of optional lunch and tastings is a significant plus. For just a bit extra, you gain a hearty, local meal paired with wines, transforming a sightseeing tour into a culinary adventure. Many travelers appreciate this opportunity, describing the wines and food as “delicious” and “absolutely worth it.”

The scenery along the Chianti road is another highlight. The views of hilltop vineyards, cypress-lined roads, and charming farmhouses provide countless photo opportunities. These vistas are what make Tuscany’s countryside famous, and this tour offers plenty of chances to appreciate them.

Considerations and Who Will Love This Tour

While the experience is highly praised, it’s worth noting that cost might be a barrier for some, especially with optional lunch and tastings. However, the private format means you’re paying for a more intimate, tailored experience—something that many travelers find justifies the expense.

This tour is best suited for wine enthusiasts who want to learn about the production process and taste high-quality wines in an authentic setting. It’s also perfect for culture lovers keen to explore medieval towns like San Gimignano without rushing. Travelers who value comfort—thanks to air-conditioned transport and WiFi—will also find this tour appealing.

If you’re after a relaxed yet immersive day in Tuscany, combining scenic beauty, history, and wine, this tour offers a comprehensive introduction that’s hard to beat.

FAQ

Is the tour suitable for non-drinkers or those under 18?
While wine tastings are for guests 18 and older, the tour itself is mainly about sightseeing and scenery. Non-drinkers can enjoy the stunning views, history, and the charming town of San Gimignano without participating in tastings.

Does the tour include lunch?
Lunch is optional and available at an additional cost (€50–€60). If you choose to include it, you’ll enjoy a hearty Tuscan meal paired with seven different wines, making for a memorable dining experience.

How long is the drive between Florence and San Gimignano?
The drive from Florence to San Gimignano takes about two hours, giving you plenty of time to enjoy the countryside and scenic vistas along the way.

What is included in the tour price?
The price covers private transportation in an air-conditioned Mercedes-Benz vehicle, all taxes and fees, bottled water, and WiFi on board. Tastings and lunch are extra.

Can I customize the tour?
Since this is a private tour, guides are often flexible and willing to accommodate preferences, whether it’s extra time in certain locations or specific interests like more wine tastings.

What is the tour duration?
The entire experience lasts approximately 7 to 8 hours, including sightseeing, winery visits, and travel time.

Are the wineries visited the same each day?
Not necessarily. The wineries may change depending on availability, but they are always selected to offer quality tastings and insights into local winemaking.

Is this tour family-friendly?
While mainly geared toward adult guests interested in wine and culture, families with older children can enjoy the scenic drives and sightseeing. Non-drinking children are welcome but won’t participate in tastings.

Final Thoughts

This private Chianti wine tour from Florence offers a well-rounded, authentic taste of Tuscany’s famed landscapes, wine, and history. With knowledgeable guides, stunning scenery, and the chance to enjoy local wines and cuisine, it’s an excellent choice for travelers who value quality, comfort, and personalized service. Whether you’re a wine connoisseur, a history buff, or simply looking for a memorable day outside Florence’s city streets, this tour delivers an experience that’s both informative and delightfully relaxing.

If you’re seeking a day that combines scenic beauty with cultural richness and delicious wine, this tour fits the bill perfectly. It’s particularly suited for those willing to spend a bit more for a private, tailored experience that offers genuine insights and authentic flavors of Tuscany.

Note: Always check availability and confirm details directly with the provider. The tour can be customized to fit your interests, and booking in advance is recommended, especially during peak seasons.