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

This experience made our article of Our 15 Favorite Siena Lunch Experiences.

Experience Tuscany in a Vintage Fiat 500 from Siena

Imagine cruising through the rolling Chianti hills in one of Italy’s most iconic small cars—the Fiat 500. This tour, priced at around $191.58 per person, lasts about 6.5 hours and offers a blend of scenic drives, charming medieval villages, and a delicious winery lunch. Led by knowledgeable guides, you’ll follow a convoy of vintage Fiat 500s, experiencing the Tuscan landscape in a way that’s both nostalgic and uniquely fun.

What we really love about this experience is its focus on personalized attention—small group sizes (limited to 10 participants) mean the guides can give you real insights and help with driving, especially for those who are comfortable with manual transmissions. Plus, the chance to actually drive a vintage Fiat brings a playful, hands-on element to your Tuscan adventure.

However, it’s worth considering that driving these older cars can be a bit challenging, especially if you’re not used to manual gears or if the vehicle has some mechanical quirks—though most reviews suggest the cars are checked thoroughly before each tour. This tour suits travelers who enjoy scenic drives, authentic towns, and wine tasting—and who don’t mind a bit of adventure behind the wheel.

If you’re after a relaxed, yet engaging way to explore Tuscany’s countryside, this tour offers a memorable blend of sightseeing, local culture, and fun driving—perfect for those who want something more interactive than a typical bus trip, and who love a touch of vintage charm.

Key Points

• Vintage experience: Drive a classic Fiat 500 through Tuscany’s landscapes.
• Small group: Limited to 10 participants, ensuring personal attention.
• Scenic stops: Explore Monteriggioni, Chianti hills, and Radda in Chianti.
• Wine and food: Enjoy a hearty 3-course lunch and wine tasting at Poggio Amorelli.
• Flexible itinerary: Includes stops at a castle, winery, and charming hill towns.
• Weather considerations: Tour runs rain or shine, with options for alternatives if weather prevents touring.

A Detailed Look at the Fiat 500 Tour from Siena

Starting the Day: Hotel Pickup and First Impressions

Your day begins with hotel pickup in Siena, a convenient way to start without the hassle of finding the meeting point. If you choose this option, it’s included in the price, which adds to the overall value—no need to worry about transport logistics after a long journey or a busy sightseeing day.

Once you meet the group, you’ll be introduced to your vintage Fiat 500, a car that’s seen better days but is full of character. Many reviews highlight the cars’ charm, though some mention mechanical quirks; it’s part of the experience. It’s worth noting that drivers must have a valid license and previous manual-driving experience, as the cars require some skill to operate safely.

Monteriggioni: Medieval Charm in Miniature

The first major stop is Monteriggioni, a tiny medieval fortress town that packs a lot of history into its ramparts. It’s often described as a fairytale setting, with well-preserved walls and towers from the Middle Ages. We loved the way the narrow streets and ancient walls evoke a time long past—perfect for wandering and snapping photos.

One reviewer called it a diminutive town with impressive ramparts, and noted the opportunity to pop into small shops. It’s a brief stop, about an hour, but enough for a quick walk and a few memories. The highlight is just soaking in the atmosphere and imagining what life was like in medieval Tuscany.

Cruising the Chianti Hills: Scenery, Villages, and a Sense of Freedom

After leaving Monteriggioni, the tour continues through the breathtaking Chianti countryside. Driving a Fiat 500 along winding country roads feels like a step back in time and offers a very tactile way to appreciate the landscape—vineyards, rustic villas, and gentle hills.

Many travelers describe the scenery as outstanding, with reviews mentioning “beautiful country side” and “picturesque grape vines.” Our guides lead the convoy, and the experience feels intimate, especially in this small group setting, letting you take in the sights at your own pace.

You might find, as some reviewers did, that the cars are a bit temperamental—stuck gas pedals or non-functioning signals—but most see these as part of the charm, a reminder that they are vintage vehicles. Our guides, like Francesco and Giorgio, are praised for their patience and friendliness in handling any mechanical issues.

Poggio Amorelli Winery: Savoring Food and Wine

The highlight for many is the lunch stop at Poggio Amorelli, a family-owned winery. The menu is a delicious display of Tuscan cuisine—from crostini with paté and fresh tomatoes to pasta with tomato sauce. The meal is accompanied by tastes of different wines, water, and a dessert wine called Vin Santo with cantucci cookies.

One guest mentioned that the lunch exceeded expectations, with plenty of food and a relaxed atmosphere. Others noted that the wine tasting was informative and enjoyable, with hospitality from the winery owner making it even more special.

Some reviews mention that the lunch might be lighter or different from expectations—cold cuts versus a hearty pasta dish—and that the wines sampled are generous but not necessarily enough to fill an entire meal. Still, most agree it’s a good value for the price, considering the setting and the quality of wine.

Final Scenic Stops and Return to Siena

Post-lunch, the group heads back toward Monteriggioni for a quick stop before returning to Siena. The drive back offers more winding roads and scenic vistas, perfect for soaking in the Tuscan air and reflecting on the day.

The tour concludes back at the original meeting point in Siena, with most reviewers expressing excitement about the fun, authentic experience.

What’s Included and What’s Not

You receive a vintage Fiat 500 to drive, a knowledgeable tour escort, the winery tour, and lunch with wine tasting. Fuel is included, so you won’t have to worry about additional costs on the day.

However, hotel pickup and drop-off are optional, and if not booked, you’ll need to arrange your own transport to the meeting point. A driver’s license and previous experience with manual gears are required, as these cars are quite old and less forgiving than modern vehicles.

Mechanical Concerns and Vehicle Condition

A few reviews mention that some Fiats are out of service or in need of maintenance. This is an ongoing challenge with vintage vehicles, and the tour provider seems proactive in checking cars beforehand. Still, it’s something potential drivers should be aware of—expect a bit of unpredictability and a sense of adventure.

Who Will Enjoy This Tour?

This experience is ideal for travelers who enjoy driving and authentic cultural experiences. If you like scenic country drives, exploring historic hill towns, and sampling Tuscan wines in a relaxed setting, this tour offers a delightful way to spend a day.

Adventurous spirits will appreciate the challenge of driving vintage cars, and those with a sense of humor about mechanical quirks will find this tour even more enjoyable. It’s also perfect for couples or small groups who want a personalized experience and to create memories that stand out from typical sightseeing.

This isn’t a tour for those looking for a luxury, hassle-free experience—the vintage cars require patience and a sense of fun. Also, if you prefer larger groups or more structured tours, this might not be the best fit. But if you’re open to a little adventure, expect genuine Tuscan charm and a day filled with laughs, scenic beauty, and good wine.

FAQs

Is hotel pickup included?
Yes, if you book the pickup option, the tour includes hotel pickup and drop-off from Siena. Without this, you’ll need to arrange your own transportation to the meeting point.

What is the minimum age to drive?
You must be at least 18 years old and hold a valid driver’s license. Previous manual driving experience is required, as the Fiat 500 is a vintage car.

How many people are in each car?
Up to two adults per vehicle. The tour limits participation to 10 travelers, with a maximum of 5 cars, to ensure a personalized experience.

What should I wear?
Comfortable shoes are recommended—avoid flip-flops, as you’ll be handling manual gears and driving the car. Bring weather-appropriate clothing; the tour runs rain or shine.

What is included in the lunch?
A three-course meal with starters like crostino and bruschetta, a main course of pasta and cold cuts, and a dessert of cantucci with Vin Santo. Wine tastings are included but not a full wine pairing meal.

Are the vintage Fiat cars safe?
The vehicles are checked before each tour, but being vintage, they may have quirks. Most reviews find them reliable enough for the scenic drive, but mechanical issues can occur.

What happens if the weather is bad?
The tour runs in rain or shine. If weather conditions are severe, the guide may alter plans or cancel with a full refund.

Can children participate?
Not suitable for children under 12. The driver must have a valid license, and younger travelers can join as passengers.

How much does the tour cost?
Approximately $191.58 per person, which includes all the key experiences—driving, sightseeing, lunch, and wine tasting.

Final Thoughts

This Vintage Fiat 500 Tour from Siena offers a genuinely different way to explore Tuscany’s iconic landscapes. The chance to drive a classic car, combined with visits to a medieval village and a scenic winery, make it a memorable day. Most travelers praise the knowledgeable guides, excellent wine, and stunning views, making it a good value for those who enjoy hands-on experiences.

While mechanical quirks and the vintage nature of the cars can be a concern for some, those with a sense of adventure and love of authentic Italy will find this tour charming and fun. It’s best suited for small groups, couples, or friends looking for a relaxed yet engaging way to see Tuscany.

If you’re ready for a day of scenic drives, storytelling, and wine tasting in a small, friendly setting, this tour is worth considering. Just pack a good pair of shoes, your driver’s license, and a sense of humor—because this is truly a day to remember.