From Firenze | Chianti day trip in a classic car

Exploring Tuscany in a Vintage Car: A Unique Chianti Day Trip from Florence

If you’re dreaming of exploring Tuscany’s rolling hills, charming villages, and iconic vineyards without the hassle of planning every detail, a Chianti day trip in a vintage car might just be what you need. This experience promises a relaxed, immersive way to see some of Italy’s most celebrated landscapes, all while cruising in style.

From what we’ve gathered from travelers and detailed descriptions, this tour offers two standout features: driving a classic, eye-catching car—perfect for photo ops—and visiting tantalizing towns like San Gimignano and Greve in Chianti that are overflowing with character.

That said, it’s worth considering that if you’re not comfortable driving a manual transmission or don’t have a valid EU driver’s license, you’ll need to opt for the chauffeur service, which adds to the cost. Still, for fans of vintage automobiles and authentic Tuscany experiences, it’s hard to beat.

This tour is ideal for small groups, couples, or friends who enjoy scenic drives, picturesque towns, and a touch of adventure behind the wheel. If you’re after a laid-back, personalized day with plenty of photo opportunities and local flavor, this could be your perfect escape.

Key Points

• Drive a vintage car through some of Tuscany’s most photo-worthy landscapes and towns.
• Visit key locations such as San Gimignano, Greve in Chianti, Panzano, and Radda in Chianti.
• Includes a delicious lunch at Borgo Vescine, with time for walks and sightseeing in charming villages.
• Small group setting (limited to 6), ensuring personalized attention and a relaxed pace.
• Flexible options: Drivers with a valid license can pilot the car, or you can opt for a professional driver for an extra fee.
• Weather-resistant: The car features a hard or soft top, with heating if the weather turns chilly.

You can check availability for your dates here:

A Detailed Look at the Experience

The Starting Point: Piazza di Verzaia

The adventure begins in Florence at Piazza di Verzaia. Here, you’ll meet your guide and fellow travelers, and get a brief overview of the route and what to expect. It’s a convenient location that sets the tone for a relaxed, local experience.

Cruising the Chianti Hills

Once behind the wheel, the first stretch takes you through some of the most scenic parts of the Chianti region. The gentle undulations of the landscape, dotted with vineyards and olive groves, unfold through the car’s windows. We loved the way the vintage car adds a tangible sense of nostalgia—driving one feels like stepping back in time, yet the views remain timeless.

Exploring Panzano in Chianti

Next up is Panzano, a quaint village famous for its authentic charm. Here, the group often stops for a walk and photo breaks. Travelers often comment on the beautiful town squares and the opportunity to see traditional Tuscan life up close. It’s a chance to stretch your legs and soak in the local atmosphere.

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Radda in Chianti: Lunch and a Break

The highlight for many is Radda in Chianti, where a two-hour stop allows for a leisurely lunch at Borgo Vescine. This medieval village offers not only delicious local cuisine but also stunning panoramic views. Many reviewers mention the quality of the food and the warm ambiance as a highlight—you’ll enjoy hearty Tuscan dishes and regional wines.

Visiting San Gimignano

The tour’s climax is a stop in San Gimignano, famous for its medieval towers that create a skyline straight out of a storybook. You’ll have about an hour to explore, photograph, and soak in the atmosphere of this UNESCO World Heritage site. It’s a favorite among travelers for its well-preserved architecture and vibrant artisan shops.

The Return Journey

After a full day of sightseeing and driving, you’ll head back to Florence, passing through the charming towns of Greve in Chianti, Poggibonsi, and more. The relaxed pace means you won’t feel rushed, and you’ll have plenty of opportunities for photos and quick walks.

What Makes This Tour Stand Out

The vintage car is more than just transportation: it’s a conversation starter and a memorable way to connect with Tuscany’s iconic landscape. The cars come equipped with both a soft and hard top, making the experience enjoyable regardless of the weather—rain or shine, you’re covered. The heating feature ensures comfort during cooler days.

The small group size (up to 6 participants) means personalized attention and a more intimate atmosphere. This setup allows for casual conversations, tips from your guide, and flexibility to enjoy spontaneous photo stops or extra sightseeing.

The guided aspect is also a plus. The tour is offered in multiple languages, including Italian, English, and Spanish, ensuring clear communication. The guide’s local knowledge enriches the experience, and you can ask questions or get tips for your own Tuscany adventures.

Is the Value Right for You?

When you consider the cost of car rental, insurance, and fuel, the experience offers good value, especially if you appreciate the allure of vintage cars and scenic drives. The inclusion of lunch and the opportunity to explore multiple towns adds to the overall package, although it’s worth noting that lunch and extras like coffee breaks are not included.

The flexibility to either drive yourself (if you have a valid license and feel comfortable with manual transmission) or opt for the driver service makes this tour accessible for different preferences. The fact that it’s a half-day means you get a satisfying taste of Chianti without a full day commitment.

The reviews give this experience a top rating (5/5), with travelers praising the service and overall experience. One review simply states, “Excellent, very good service,” highlighting that the tour delivers on its promises.

Who Should Consider This Tour?

This experience is best suited for adventure-loving couples, small groups of friends, or vintage car enthusiasts looking for a relaxed but memorable way to explore Tuscany. It’s perfect if you’re keen on driving a classic vehicle, enjoying authentic scenery, and visiting iconic towns in a comfortable, intimate setting.

However, if you’re not comfortable driving a manual or don’t have a license, don’t worry—an additional cost for a driver is available. Those seeking a more structured or guided experience without driving might prefer other options, but for lovers of open-road exploration, this tour hits the mark.

Frequently Asked Questions

Do I need a driver’s license to participate?
Yes, if you want to drive the vintage car yourself, you need a valid EU driver’s license and to be comfortable with manual transmission. Otherwise, a driver service is available at an extra charge.

How long is the tour?
The tour lasts approximately 6 hours, with multiple sightseeing stops, lunch, and free time for walks and photos.

What should I bring?
Bring your passport or ID card, driver’s license (if you plan to drive), sunscreen, a hat, or scarf for sun protection.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund. It’s flexible enough for most travel plans.

Is lunch included?
Lunch at Borgo Vescine is not included in the tour price but is available during the stop at Radda in Chianti.

What if it rains?
The car has a soft or hard top and heating, so you’ll stay dry and comfortable regardless of the weather.

Is this experience suitable for children?
The tour is designed for adults, especially since driving requires a valid license. Children can enjoy the scenery but would need to be accompanied by adults.

Are there other experiences similar to this?
Yes, there are other small-group wine and food tours, Vespa excursions, and even luxury Ferrari drives. Links to similar options are provided for those interested in broader Tuscan explorations.

Final Thoughts

This vintage car tour offers a distinctive way to experience Tuscany’s heartland—combining scenic drives, charming towns, and a touch of nostalgia. It’s perfect for travelers who want to skip the tourist bus and instead enjoy a personalized, relaxed day exploring at their own pace.

The opportunity to drive or be driven in a classic car, paired with visits to renowned villages like San Gimignano and the wine-rich hills of Chianti, makes it a memorable choice. The small group format ensures comfort, while the flexible options and beautiful scenery cater to a variety of tastes.

For those who cherish authentic experiences, love picturesque settings, and aren’t afraid of a little driving adventure, this tour offers excellent value and a chance to create lasting memories in Tuscany. It’s a perfect fit for classic car fans, romantic couples, or small groups seeking a truly special day out.

Whether you’re a vintage car enthusiast, a lover of Italian scenery, or just after a different way to see Tuscany, this tour delivers a charming, personable experience that’s worth considering. Just remember to bring your driver’s license and a sense of adventure.

You can check availability for your dates here: