Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

This review takes a close look at the Vintage Fiat 500 Tour from Siena, an experience that promises to turn your classic Italian dreams into reality. While we haven’t done it ourselves, we’ve gathered plenty of insights from travelers who have, along with the details from the tour provider. If you’ve ever wanted to cruise the Tuscan hills in an adorable vintage car, this might just be the adventure for you.

What we love most about this tour is the chance to see Tuscany in a truly different way — cruising through scenic landscapes in a tiny, charming Fiat 500, and stopping at authentic wineries and charming hilltop towns. The small-group limit of just ten people ensures a more personal, relaxed experience, and the included winery lunch offers a taste of local flavors that’s well worth the price.

On the flip side, it’s worth noting that vintage cars come with their quirks — some reviews mention mechanical issues, and the cars might not be as smooth or reliable as modern vehicles. Plus, the tour is centered around driving and enjoying the scenery, so if you’re more into museums or structured sightseeing, this might not be your ideal choice.

This experience suits travelers looking for a fun, offbeat way to explore Tuscany, especially those who enjoy driving manual transmissions and are open to a bit of adventure behind the wheel. It’s perfect for couples, small groups of friends, or anyone wanting a memorable day immersed in Italian charm.

Key Points

• Unique Experience: Cruising Tuscany in a vintage Fiat 500, a truly classic Italian charm
• Small Group: Limited to just ten participants, ensuring personalized attention
• Scenic Drive: Pass through Monteriggioni and Chianti hills, with plenty of photo-worthy stops
• Tasty Lunch: Enjoy a hearty three-course lunch paired with local wines at Poggio Amorelli
• Driver’s Skill Required: Manual driving experience is necessary, and drivers should be comfortable with vintage cars
• Weather Considerations: Tour happens rain or shine, with safety being a priority in stormy weather
• Cost & Value: At about $192 per person, it offers a memorable blend of scenery, culture, and fun driving

Driving Through Tuscany in a Vintage Fiat

Imagine yourself behind the wheel of a 1960s Fiat 500, zipping along narrow country roads lined with cypress trees and vineyards. This isn’t just a sightseeing bus tour — it’s a hands-on experience that puts you in control of a piece of Italian automotive history. And you’ll be doing this in a small caravan led by your guide, which makes the entire day feel intimate and relaxed.

The experience kicks off from Siena with a pickup included if you select that option, making logistics straightforward. Once you’re all set, you get briefed on the vehicles, which are vintage and charming but can also be temperamental. Several reviews highlight mechanical quirks, but most see this as part of the fun and charm — a reminder that you’re driving a classic car, not a brand-new model.

Exploring Monteriggioni and Chianti

Your first stop is Monteriggioni, a tiny medieval walled town that’s perfect for wandering and soaking up history. The walls, ramparts, and small shops give a real sense of stepping back in time. As one traveler put it, “The scenery, towns, and wineries were outstanding,” capturing the essence of what this tour offers.

From there, the drive continues through the rolling hills of Chianti, a landscape dotted with vineyards, rustic villas, and olive groves. The wide-open views and twisting roads are what make this drive special. Multiple reviews mention the scenic beauty and how the drive itself is a highlight, with one noting it’s a “beautiful countryside” that’s perfect for a leisurely cruise.

The Winery Lunch: Good Food and Fine Wines

At Poggio Amorelli, the group gathers for a three-course lunch paired with wine tasting. The menu features starters like crostini with tomato or olive pâté, followed by pasta with tomato sauce, and a dessert of biscotti with Vin Santo. Reviewers consistently mention the good food, with one describing it as a “hearty Tuscan three-course lunch,” while others point out the wine tastings are generous and well-selected.

A few reviews note that the lunch isn’t a full sit-down affair but more of a tasting platter, which is consistent with the description. Still, the wines receive praise, and the owners’ hospitality makes the visit memorable. Many enjoy the opportunity to learn about local wines, which adds depth to the experience.

The Return Journey and Overall Atmosphere

After the winery, the group heads back toward Siena, often with a quick stop in Monteriggioni for some final photos. The entire day averages around six and a half hours, packed with scenic drives, cultural stops, and good company.

What really comes through from travelers’ comments is that the guides are a huge part of the experience. Several reviews rave about the knowledgeable, enthusiastic guides who keep things fun, share local insights, and manage the vintage cars smoothly. One reviewer said, “Diego drove our Fiat and was great,” emphasizing how important the guide’s personality and competence are to the overall enjoyment.

Practical Details and Considerations

The tour is priced at $191.58 per person, which is a fair value considering the combination of driving experience, sightseeing, lunch, and wine tasting. It’s worth noting that most travelers book about 68 days in advance, so if this sounds appealing, plan ahead.

Participants need to have a valid driver’s license and be comfortable with manual gear shifts — the cars are vintage, manual transmission only. The maximum group size of ten travelers ensures plenty of attention from the guide, but it also means the experience is intimate, not crowded.

The tour includes hotel pickup and drop-off if selected during booking, but be aware that without this, you’ll need to meet the group at the specified location in Badesse. Also, the activity runs rain or shine, with safety a priority if weather conditions are severe.

While the experience is generally suitable for most travelers, it’s not recommended for children under 12, and drivers must be at least 18 years old. Be prepared for some mechanical quirks — a few reviews mention car issues — but most see these as part of the charm of vintage driving.

What Do Travelers Say?

Reviews paint a mostly positive picture, with many praising the scenery, the guides, and the wine. For example, “Brilliant way to experience the Chianti Wine Region,” and “Loved driving the the cutest little cars,” capture how enjoyable and memorable this adventure is. Travelers also appreciate the small-group setting, which allows for more personal interaction.

Some concerns are raised about the mechanical condition of the Fiats. A couple of reviews mention that many cars were out of service or had issues, which could be disappointing if you’re expecting a smooth ride. Others highlight that the cars are old and may require patience and a sense of humor.

The lunch, described as light but tasty, complements the drive without feeling overly formal. And many reviewers say they’d do it again or recommend it for a special occasion, especially if they enjoy driving or want a different way to explore Tuscany.

Who Is This Tour Best For?

If you’re someone who loves driving manual cars and wants a hands-on experience, this tour is a fantastic choice. It suits travelers looking for an active, fun day that combines scenic beauty with a touch of nostalgia. It’s especially good for couples, small groups, or anyone who appreciates a quirky, memorable way to see Tuscany.

However, if you prefer a fully guided, no-driving experience or are worried about vintage car reliability, this might not be your best pick. Also, if you’re traveling with very young children or have mobility restrictions, consider whether the stops and driving might be less suitable.

Final Thoughts

The Vintage Fiat 500 Tour from Siena offers a charming way to see Tuscany that’s more about participation than mere sightseeing. You’ll love the chance to drive a piece of Italian history, enjoy spectacular views, and taste the region’s wines in an authentic setting. The small-group format ensures a cozy, personal vibe, and the guides are generally praised for their friendliness and knowledge.

While the vintage cars may have quirks, most travelers see this as part of the adventure — a reminder that sometimes the journey isn’t just about the destination, but the stories you create along the way. This tour provides a playful, engaging way to experience Italy’s countryside, perfect for those who want to add a little excitement to their trip.

If you’re craving a mix of scenic drive, cultural stops, and good wine with a side of nostalgia, this could be just the experience you’re looking for. Just be sure you’re comfortable with manual driving, and keep an open mind about the vintage cars’ quirks. It’s a day that’s likely to leave you with plenty of stories and a big smile.

Frequently Asked Questions

Do I need to have driving experience?
Yes, you must have experience driving a manual transmission, as the vintage Fiat 500s are stick-shift only. You should also be comfortable with vintage cars, which might not have the smoothness of modern vehicles.

Is the tour suitable for children?
The tour is not available for children under 12 years old, and drivers must be 18 or older. The activity involves driving vintage cars, which isn’t ideal for young children or those with mobility issues.

What’s included in the price?
Your ticket covers the vintage Fiat 500 rental, a guide, a winery tour, a three-course lunch, wine tasting, water, and fuel. If you opt for hotel pickup and drop-off, that is included as well.

How long does the tour last?
It’s approximately 6 and a half hours, including driving, stops, lunch, and sightseeing. Expect a full but relaxed day exploring Tuscan hill towns and vineyards.

What should I wear?
Since the cars are open-top, wear comfortable shoes and bring sunglasses. Wear weather-appropriate clothing; the tour runs rain or shine.

Are there any safety concerns?
The cars are vintage but checked thoroughly before each tour. The guide manages safety closely, but mechanical issues can occur, so patience and a sense of humor are recommended.

Can I cancel or reschedule?
Yes, there’s free cancellation available up to 24 hours before the tour. No refunds are given if you cancel less than 24 hours beforehand or if the tour is canceled for safety reasons due to weather.

In the end, this tour offers a blend of driving, sightseeing, and tasting that’s perfect for those eager to see Tuscany from a different angle — with a little vintage flair.