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Experience Tuscany in a vintage Fiat 500 on this 4-hour Chianti tour including scenic drives, medieval villages, and wine tasting for $149.46 per person.

The Chianti Classic Vintage Fiat 500 Tour offers a rare chance to explore Tuscany’s iconic countryside in a 1950s Fiat 500. Priced at $149.46 per person, this 4-hour experience is ideal for those eager to enjoy a vintage vehicle adventure amidst picturesque vineyards and medieval villages. The tour begins from Badesse, Siena, and includes pickup options, making logistics straightforward for participants. With a limited group size of up to 8 travelers, the tour maintains an intimate and relaxed atmosphere.
This tour stands out by combining scenic drives in a classic car with visits to Chiantian villages and a wine tasting experience at a local winery. It is especially suited for auto enthusiasts, wine lovers, and anyone looking for a fun, nostalgic journey through Tuscany’s landscape. While participants must be at least 18 years old to drive, it offers an engaging day with self-driving opportunities or accompaniment by a professional escort.

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The tour kicks off at Via della Resistenza, 95, Badesse, where a professional guide greets the group. The pickup service can be arranged, easing access for travelers staying nearby. The meeting point is conveniently located near public transportation, making it easy to reach.
Once assembled, the vintage Fiat 500 becomes your vehicle for the day, and the guide provides an overview of the route and stops. The group size of up to 8 ensures a personal experience with plenty of space for up to 3 passengers per car.

The journey begins along Strada Statale 222 Chiantigiana, a renowned route winding through hills dotted with vineyards and olive groves. The classic Fiat 500 adds a nostalgic touch to the landscape, allowing passengers to enjoy the open air and views. The one-hour drive sets the tone for a relaxed, scenic exploration of the Chianti region.
This stretch offers sweeping views of the rolling hills, helping visitors feel like they’re stepping into an old Italian film. The slow pace and vintage charm make every mile feel special, providing ample opportunity for photos and soaking in the Tuscan atmosphere.

The tour stops for about an hour at Castellina in Chianti, a medieval village famous for its Rocca and romanic-style church. Visitors have time to walk around the walled town, take photos of its historic architecture, and enjoy its quaint shops.
The medieval feel of Castellina offers a glimpse into Tuscany’s past, with narrow streets and stone buildings that have stood for centuries. This stop provides authentic scenery and history without the crowds often found in larger towns.

The next stop includes a visit to a Chianti winery, where the group enjoys a photo break at a scenic viewpoint. Here, participants can appreciate breathtaking vistas of the countryside, perfect for capturing memories.
Following the photo stop, the tour offers a typical lunch at the winery, featuring regional dishes served amidst the vineyard backdrop. During this time, guests can also participate in a wine tasting, sampling local wines produced in the Chianti area. This cellar tour and tasting deepen the appreciation for Tuscany’s renowned wine culture.

The day concludes with a drive back to the meeting point in Badesse, allowing travelers to reflect on their scenic experience. The final hour in the vintage Fiat 500 ensures a leisurely return, often filled with conversation about the countryside and the history encountered.
Participants then have the option to relax after their 4-hour adventure, with drop-off options available if booked in advance. The tour ends back at the initial meeting spot, making logistics simple and stress-free.

The tour includes a vintage Fiat 500 car, a professional escort, a cellar tour, and wine tastings. It is designed for adults aged 18 and above who are comfortable driving the vehicle, with driver’s license and credit card required for rental.
Participants must be at least 13 years old to join as passengers, and up to 3 people can share a vehicle. The tour is available rain or shine, with contingency plans such as alternative dates or refunds in case of severe weather.
The price of $149.46 per person is competitive, especially given the inclusion of scenic drives, stops, wine tasting, and lunch. Advance booking is recommended, typically 71 days in advance, ensuring a spot on this popular experience.

One of the most praised aspects of this tour is the fun of driving a vintage Fiat 500, which provides a unique connection to Italy’s automotive past. The scenic routes along Chianti’s hills are some of the region’s most beautiful, and the medieval villages like Castellina in Chianti bring history to life.
Unlike some tours that only feature sightseeing, this experience combines driving, tasting, and cultural stops into a well-rounded day. The limited group size makes for a friendly atmosphere, and the professional escort ensures smooth navigation and commentary.
While the tour is accessible for most, drivers must be able to operate a manual transmission and be at least 18 years old. The vehicle’s size restricts the group to three per car, so booking early is advised for those traveling with friends or family.
Since alcoholic beverages are served during the wine tasting, only adults 18 and over can participate in wine consumption. Children under 13 are not permitted on the tour, aligning with safety regulations.
The Chianti Classic Vintage Fiat 500 Tour stands out for its nostalgic charm and scenic immersion in Tuscany’s countryside. The combination of vintage driving, medieval stops, and wine tasting creates a leisurely, engaging experience perfect for auto lovers, wine enthusiasts, or those simply seeking a memorable day through Italy’s rolling hills.
While the 4-hour duration keeps it manageable for most itineraries, the tour offers ample opportunities to enjoy breathtaking views and delight in regional flavors. The small group size and professional guidance ensure a personalized journey through one of Italy’s most beloved regions.
“It was a blast trying to drive the vintage Fiats built in 1950s. A true appreciation of the automobile evolution was formed. Until you experience…”
Can I drive the vintage Fiat 500 myself?
Yes, drivers must be at least 18 years old and possess a valid driver’s license and a credit card for the rental agreement.
Is the tour suitable if I don’t want to drive?
The tour is designed for those comfortable driving, but alternatives like the “ape calessino” can be offered if the guide assesses insufficient driving skills.
What is included in the price?
The price covers the vintage Fiat 500, escort, cellar tour, and wine tasting. Lunch is also part of the experience at the winery.
Are children allowed?
Children under 13 are not permitted to join.
Can I book this tour last-minute?
Advance booking is recommended, as it is usually booked about 71 days in advance. The tour offers free cancellation up to 24 hours before the start.
What happens in case of bad weather?
The tour runs rain or shine. In case of severe weather, an alternative date or a full refund is provided.