BEAUTIFUL TUSCAN WINE ESTATES BY VINTAGE FIAT 500 FROM FLORENCE

Last Updated on 2nd March 2026 by Bejal

The vintage Fiat 500, is the epitome of Tuscan countryside cruising, in our opinion. Winding country roads, the low September sun in your face, Raybans pushed back on the bridge of ones nose, weaving effortlessly through narrow lanes seeming purposefully made for this 1960’s classic. If you are considering booking a tour in a vintage Fiat 500 from Florence, read on to learn more about the experience packed with useful tips and what to expect.

Pin & Save

If you’ve read our article on the Vespa experience you’ll already be familiar with the booking process via Withlocals and We Like Tuscany. we’ve linked the post below if you fancy a read or refresh!

Related Article: Vespa Tour From Florence To The Chianti Hills, Tuscany

The Best Time to Take a Fiat 500 Tour From Florence?

We would say when it’s dry! So opt for shoulder season or summer but bear in mind, summer can be very busy and hot in Florence and Tuscany. We did ours in late September. We opted for an afternoon slot so we could take a drive and enjoy a nice leisurely lunch at a vineyard with wine. It therefore worked out well that these particular vintage Fiat 500s could only be driven by a guide rather than self drive.

Things to Consider Before Booking Your Fiat 500 Tour

As always before booking your trip, we’d recommend the following considerations:

• Does the tour involve you driving the Fiat 500 or will there be a guide/driver that will accompany you?
• The time of year you’ll be taking part in the experience.
• Would you like a half day morning or afternoon experience?
• If you are self driving, do you feel confident driving in Italian traffic and know the local regulations?

Be-lavie Tip: Do note that some tour companies and experiences do not allow you to drive their Vintage Fiat 500s. This is certainly the case with We Like Tuscany and Withlocals. These cars are classics and they don’t want anything going wrong and incur huge costs as on some occasions things just can’t be fixed.

Vintage Fiat 500 From Florence: The Experience

We met Montague or Monte, our Fiat 500 chauffeur and guide, at midday at the We Like Tuscany HQ in Oltrarno. Shortly after, we were swiftly introduced to the most beautiful little, but perfectly formed lady ever created, Tiffany more widely known as a vintage 1960’s Fiat 500. Why is this adorable lady named Tiffany? Well if you hadn’t guessed, her armour sports the medium light robin egg blue colour associated with Tiffany & Co.

Once we acquainted ourselves with Tiffany, by that I mean I bagged the passenger seat and Dr C sat in the back, it was time to set off on our four hour jaunt of the country!

The first stop was Piazzale Michelangelo, we headed straight for one of our most favourite views in Florence on San Miniato hill, where stands the San Miniato Basilica with breathtaking panoramas of Florence city.

Monte shared his knowledge of the church and surrounding area with us and after a short photo opportunity, we continued our journey past the birthplace and location of imprisonment of the famous astronomer, physicist and engineer Galilei Galileo.

Another photo opportunity came at a low stoned wall with the city of Florence in the distance and the observatory to the right. This is where Tiffany sported her model like finesse.

It was then time to meander through the beautiful Cyprus tree lined roads into the heart of Tuscany and more specifically Chianti. The most charming drive looking over farm houses, Cyprus tree guarded driveways and terracotta rooftops into the barely visible distance. We listened to Monte’s facts about the area and historical snippets of information that he shared in a region he chose to call his home.

The scenic Tuscan roads lead us along olive groves, medieval castles, vineyards and a number of wine estates.

Villa Le Corti & Principe Corsini Wine Estate

After all that cruising we’d worked up an appetite and right on cue we arrived at Principe Corsini. A beautiful rustic family owned wine estate in San Casciano. The villa, Villa Le Corti, is the Corsini family’s historic reside estate in Chianti overlooking 250 hectares of land of which 49 are vineyards, planted with Sangiovese grapes providing a lovely rich Chianti Classico.

Monte accompanied us on a tour of the stunning gardens surrounding the villa to take in the incredible panoramic views.

Our guide, Monte also took us down to see where the Villa Le Corti wine was produced, as grapes were being harvested during our visit in late September and gave us a little insight into the wineries business. Villa Le Corti also produces great quality olive oil, which we sampled at lunch, where the family still picks all the olives by hand to use in their delicious oil.

Lunch At Oseteria Le Corti

All wines can be purchased on the their website or in their Osteria Le Corti, where we proceeded for a tasting of three of their delicious wines and enjoyed a three course lunch.

The Osteria is located in the building housing the wine cellars. All the food is paired beautifully with the selection of Principe Corsini wines and prepared by chef Laura Ceccherini. The dishes are made from locally sourced fresh ingredients. We started with drizzling some of the Principe Corsini Olive oil on some fresh bread whilst we worked our way through the wine selection.

To start, it was pecorino cheese and potato croquettes, next a main of ravioli and to finish a panna cotta with a thick grape jus.

Post lunch it was time for a little walk around the estate and a relaxing drive back to Florence in our little lady, Tiffany.

Top Facts About Fiat 500

• Fiat 500s were launched in Italy in 1957, infact the original model was manufactured at the Lingotto Plant in Turin.
• The Fiat 500 was designed by Dante Giacosa to be driven in the narrow myriad of streets in the cities of Italy.
• The car was originally called “Cinquecento” and was marketed as an affordable, functional, and economical city car following the war in Italy. 
• The very original model was a two door car with a 479 cc, air cooled, two cylinder engine, and could only reach a maximum speed of 53 mph.
• The Fiat 500s production unfortunately stopped in 1975 as consumers wanted much more luxurious cars.
• According to Fiat,  about 400,000 of the original Fiat 500s are still being used today. In total only 3,893,294 Fiat 500’s were built. 
  

Top Tips About Driving The Fiat 500

• You must be over 18 to drive a Fiat 500 in Italy.
• If you are planning to drive a Fiat 500 in Tuscany, make sure you have a full driving license from your country of residence.
• Ensure you have adequate car insurance to cover you for anything accidental, should it occur.
• Make sure you are aware of Italian driving regulations and are confident driving in Italy.
• It goes without saying always wear your seat belt at all times and ensure that your passengers do to.
• You may not realise but those with long legs may find it difficult to sit and more difficult to drive these small cars. Vintage Fiat 500’s in particular do not have much legroom so driving yoursefl may not be the greatest of ideas.
• Vintages Fiat 500’s are generally two door and if you’re tall quite tricky to get in and out of.

Be-lavie Tip: Remember if you are having lunch with wine or visiting wine estates, then it’s best to have a driver or guide take you around. Don’t risk consuming alcohol and driving.

Recommended Florence & Chianti Tours

Although this Vintage Fiat 500 experience with We Like Tuscany is a great way to explore the area, there are some other tours which focus on self-driving in a small group, which you may want to consider too if you prefer this style. Additionally a few Chianti Hill tours which are perfect for small groups if you have a larger party and can work out more cost effective.

Vintage Fiat 500 From Florence Tour: Round Up

A fantastic knowledgeable and friendly guide, the Tuscan hills as a backdrop and the star of the show Tiffany, our Vintage Fiat 500. Oh and lets not forget a great lunch and vino! If you’re looking for a relaxing afternoon away from the city crowds this experience is a perfect way to see the surroundings as well as experience sitting in a Fiat 500.

This is a memorable tour, which we loved because we got the chance to sit back and enjoy the experience, rather than having to worry about focussing on driving the Fiat 500. Having a guide and driver most certainly has its advantages.

**Disclaimer: Be-lavie received a press rate for the Fiat 500 experience in exchange for this review for Withlocals. All opinions, views and photography are honest and our own, and as always remain a copyright of Be-lavie.

The Details

• Street Address: We Like Tuscany I Via del Campuccio, 88 I 50125 Florence. I Tel. +39 342 935 2395.
• Find it Here: Map Location.
• More information: We Like Tuscany.
• Reviews: Read what other We Like Tuscany customers are saying.
• Price Range: $$, personalised experiences do cost more as you’d expect but are totally worth it.

 

 

Related Articles to Vintage Fiat 500 From Florence

• 9 of the most Amazing Postcard-friendly Views of Florence
• Oltrarno: An Artisanal Neighbourhood in Florence
• A Luxury Stay At The Belmond Villa San Michele, Fiesole
• SoprArno Suites: A beautiful Boutique Hotel in Florence
• Ad Astra Florence: A Beautiful Hotel Located In Private Gardens
• A Luxury Stay At The Beautiful Bernini Palace Hotel
• The Best Fine Dining Restaurants in Florence
• Where To Find Vegetarian-Friendly Food in Florence
• La Bottega del Buon Caffe – Michelin Star Review
• Il Locale Firenze: Contemporary Fine Dining in Palatial Surroundings
• A Vespa Tour From Florence into The Chianti Hills, Tuscany
• An Artisan Tour of Oltrarno
• A food tour of Florence with a local
• A cookery lesson in Florence with The Cooking Lab

Resources To Help Plan Your Trip

À bientôt

Pin & Save