When we were planning our 30th anniversary trip to Italy, we knew we wanted to do something unforgettable. Seeing Michelangelo’s David and eating Florentine steak were definitely on the list, but we also wanted to escape the busy city crowds of Florence and see the rolling hills of Tuscany.
Enter the Self-Drive Vintage Fiat 500 Tour.
If you have ever romanticized driving a classic Italian car through the sun-drenched vineyards of Tuscany (and let’s be honest, who hasn’t?), this experience needs to be on your radar. Here is our honest review of the tour, what to expect, and what you should pack for the ride!
What is the Vintage Fiat 500 Tour?




This isn’t a tour where you just sit in the back of a bus and look out the window. You actually get the keys to a beautifully restored, classic 1960s Fiat 500.
We booked the Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine.
The tour starts in Florence, where you meet your guide and get acquainted with your car. Good Journey Tip: These classic cars are manual transmission (stick shift), so make sure the designated driver in your duo is comfortable using a clutch!
Once everyone is ready, you follow your guide in a colorful convoy out of the city and into the breathtaking Chianti wine region.
The Experience: Tuscan Hills and Italian Cuisine

Driving this tiny, zippy car through the winding, cypress-lined roads of Tuscany is just pure joy. It feels like you have stepped onto a movie set. The guide takes you along quiet, scenic routes with plenty of stops to stretch your legs, take photos, and enjoy the panoramic views of olive groves and vineyards.
The climax of the tour is pulling into a stunning Renaissance villa and wine estate. After a fantastic drive, we sat down to an incredible, authentic Tuscan meal featuring local meats, cheeses, and (of course) wine. It was one of the most romantic and memorable afternoons of our entire 17-day anniversary trip.
Is the Tour Worth the Money?
Absolutely. It is a premium experience, but it delivers on every single level. You aren’t just paying for a meal; you are paying for the thrill of driving an iconic piece of Italian history, the safety of having a guide navigate the Tuscan roads for you, and a fantastic culinary experience.
If you are planning a honeymoon, anniversary, or couples’ trip to Florence, we cannot recommend this enough.
- Book it here: Check availability and prices for the Fiat 500 Tour here. (Note: This tour frequently sells out, especially in September/October, so book well in advance!)
What to Pack for Your Tuscan Road Trip

Because the classic Fiats are small and lack modern AC, you want to be comfortable! Here are a few travel essentials we highly recommend bringing along for this tour:
- Polarized Sunglasses: The Tuscan sun is incredibly bright, especially when bouncing off the winding roads. A good pair of polarized sunglasses is an absolute must for whoever is driving. These are our favorite lightweight polarized travel sunglasses.
- An Anti-Theft Crossbody Bag: Space is tight in a vintage Fiat! Instead of a bulky backpack, we use a sleek, anti-theft crossbody bag to hold our passports, wallets, and phones. It fits perfectly at your feet or on your lap. Check out this great travel crossbody bag.
- A High-Capacity Power Bank: You are going to take a ridiculous amount of photos and videos of the car and the scenery. Don’t let your phone die halfway through the tour! We never leave the hotel without this compact, fast-charging power bank.
Where to Stay in Florence

For our 4 days in Florence, we decided to book a local apartment, the RED PEARL Airbnb, which gave us a fantastic, authentic home base to return to after our Tuscan drive. If you prefer hotels with amenities, Florence has incredible boutique options right in the city center.
- Browse Florence Accommodations:
Would you feel confident driving a manual classic car through Italy?
Read Next: The Ultimate 17-Day Italy & Greece Anniversary Itinerary (Rome to Santorini)

