







Get behind the wheel of a vintage Cinquecento. Over 300 drivers have taken the restored classic out of Florence and into the Chianti hills, following a guide by radio past cypress lines, vineyards and old farmhouses. Manual gears, fuel and insurance included. Pick your date and start the car.
A Fiat 500 rental in Florence, Italy, here takes the form of a guided countryside drive: the car is provided for the day, and you drive it yourself through the hills south of the city.
What you get is the restored vintage car, a guide leading the route, fuel, insurance and a ham and cheese tasting, in five hours.
The closest match is the Florence Countryside Vintage Fiat 500 Driving Tour. It gives you a real vintage Cinquecento to drive, but on a set route in convoy with a guide, not an open rental you take wherever you like.
If your goal is the drive itself, the countryside around Florence is the best place for it: quiet secondary roads, cypress-lined avenues and hill views.








A standalone vintage Fiat 500 rental is not on sale here, so this page recommends the next best thing: a five-hour drive where the car is yours for the whole day out.
The Florence: Countryside Vintage Fiat 500 Driving Tour includes the rental of a beautifully restored Cinquecento, picked up from a garage near the centre that once served as a palazzo's coach house.
A guide shows you how the 1960s gearbox works, then leads a convoy through the streets and out along a cypress-lined avenue into the hills.
You drive quiet secondary roads at an easy pace, stop at one of Florence's oldest churches, and finish with Tuscan ham, cheese and a glass of Chianti on a private terrace. Fuel, guide, two-way radio and insurance are all included.
The trade-off is clear: the car is reserved for the guided route rather than free hire on your own itinerary, and there is no hotel pickup. Even so, it gives you the real thing behind the wheel, with a lead car handling the navigation.
It suits anyone comfortable with a stick shift; drivers must be 18 or older with a valid licence, and the rear seats have no belts. Book a few weeks ahead in high season.



Green marks the lowest price. Prices per person.




The first thing worth seeing arrives before you leave town: the view of Florence from the cypress-lined avenue on the way out of the city.
On this five-hour drive you take the wheel of a restored vintage Fiat 500, follow a guide in convoy through quiet country lanes, and stop along the way for photos, a church visit and a tasting.
The rental part is real: the restored car is included, as are fuel, insurance and a two-way radio to hear your guide. What you get in return for five hours is rolling Tuscan hills, villages, a terrace overlooking the countryside, and a glass of Chianti with ham and cheese at the end.













You collect your restored Fiat 500 from a garage that was once the stables and coach house of a Florentine palazzo. The guide introduces the quirks of driving a car from the 1960s before you set off through the streets of the city.

Leaving the center behind, the route climbs an avenue lined with cypress trees. The trees give the drive its classic Tuscan frame, and the views over the city open up as you go.

The first stop is one of the oldest churches in Florence. You step inside for a short visit, then take photos with your Fiat 500 in front of the city spread out below.

From there the convoy follows quiet secondary roads through villages and country lanes at a relaxed pace. Your guide stays in two-way radio contact the whole way, and there are stops for photos of the rolling hills.
The drive ends on a private terrace overlooking the Tuscan hills. You taste a selection of Tuscan ham and cheese with a glass of Chianti before heading back to Florence with the guide.

Amazing experience with wonderful guides Leo and Antonio. Supportive, informative, great vibes.

Leo made sure everyone was comfortable driving manual and walked through everything on the old cars. Super knowledgeable, kept the group together, answered everything.

Christian and Helena were excellent guides. Luxurious bus to the Fiat garage, great lunch and scenery. Mechanic Massimo blocked roads for safe crossings.

Lots of fun, great mix of travellers, Vespas plus us in vintage Fiats. Training took time but Antonio made everyone comfortable. Then we were off! Nice pasta meal, wine for all. Very nice experience.

LEO WAS THE COOLEST GUIDE!!!! Worth every penny. Staff took time for a one-on-one with the vehicle.

BRILLIANT! Fun from the start. Leo was knowledgeable, involved and kept everyone safe. Cars were a blast, especially for petrol heads, and he knew the best photo spots.

Very well run tour, vehicles in excellent condition. Instructions and a quick driving test made sure we were comfortable. Leo was helpful and entertaining, lunch was tasty. We all loved our day, highly recommend!
Most reviewers praise the guides by name, from Leo to Bella, for their patience with the old cars.
Many travelers found the driving lesson easier than expected and loved lunch at a hillside villa.
Several wished they had booked the lunch or picnic option, after hearing about it from other guests.
Choose the day you want to drive the Tuscan hills and book the Florence: Countryside Vintage Fiat 500 Driving Tour. You can cancel up to 24 hours in advance for a full refund, so a date fixed a few weeks out stays flexible.
Read what the booking includes before you pay: the restored Fiat 500, the guide, a two-way radio, fuel, insurance, and a Tuscan ham and cheese tasting. Hotel pickup is not included, so plan to reach the garage in Florence yourself.
Make sure the person who will drive is at least 18, holds a valid driving licence, and can use a stick shift. This vintage car has no automatic version, and an automatic-only driver cannot take the wheel.
After payment you get a voucher and confirmation with the meeting details. Check the start time, note where to collect the car in Florence, and see what the operator says to bring on the day.
Turn up at the meeting point with a little time to spare. The guide hands over the car, walks you through driving a 1960s Fiat 500, and you set off once everyone feels confident with the clutch.
Both self-drive outings use cars with a stick shift, and the Chianti tour opens with a lesson in the double-clutch before you set off. A vintage 500 needs more attention to its gears than a modern car, and it can feel sluggish uphill. The pace stays relaxed, so the hills are manageable if you drive slowly.
Book about 2 to 4 weeks ahead for a Florence food or wine outing, because wineries fill quickly during the harvest. For a summer trip generally, 10 to 12 weeks of lead time is the sensible window. Popular dates go early in Tuscany.
Each countryside car carries a maximum of 3 adults, or 2 adults and 2 children aged 3 to 12, who ride free of charge. The winery and lunch tour is priced per car rather than per person, and each car holds 2 guests plus the private driver.
Every Florence drive on this page lets you cancel up to 24 hours in advance for a full refund. That covers the countryside tour, the Chianti self-drive, the picnic tour and the winery lunch. Plans shifting a day or two out cost you nothing.
You must present a valid driving licence to drive, and the minimum age is 18. The Chianti tour asks for a driver who is already a regular manual-car driver, since it is not a driving lesson. Bring a credit card too, as the Chianti outing needs it for insurance purposes.
The countryside drive bundles the essentials into the booking:
The picnic tour rules out wheelchair users, anyone over 6 ft 6 in (200 cm) and anyone over 309 lbs (140 kg), and the winery tour excludes pregnant women and people with mobility impairments. The nominated driver must feel fully confident in a manual car; automatic-only drivers cannot drive on the picnic tour.
The countryside tour states plainly that its rear seats have no safety belts fitted, so children ride in cars on the understanding that the front takes an adult. If you plan to carry kids in the back, weigh that fact before you book.
The Chianti self-drive tour lists a 15-euro gas surcharge and gratuities as extras you pay separately. The countryside tour covers fuel and insurance in the booking, so nothing further comes up there. Hotel pickup and drop-off sit outside both tours.
The countryside tour starts at a garage in Florence that once served as the stables and coach house of a palazzo, where the guide walks you through driving a car from the 1960s. None of the self-drive tours include hotel pickup, so plan your own way there.
Florence's restricted-traffic zone covers the historic centre, and electronic gates photograph your plate, so an unauthorised entry brings an automatic fine. If you drive the car yourself, park outside the zone and walk in. The guided tours route you out of the city, so the zone never becomes your problem on them.
The drives leave Florence for quiet secondary roads in the hills, always in convoy behind the guide and in radio contact. Tuscan country lanes run narrow and winding, and you may meet a bus or truck coming the other way. Long stretches rarely pass 40 mph, so leave buffer time and stay alert on curves.
























The garage where your vintage Fiat waits was once the coach house of a Florentine palazzo, and four such days run out of Florence, three with you at the wheel. Choosing between them is the whole decision, and the countryside drive leads the field.

The five-hour countryside drive hands you the keys to a restored 500, with fuel and both insurances covered.
Every car here is a manual: bring your licence, and an International Driving Permit too if yours is a non-EU licence.
Cancel free up to 24 hours ahead, and book about 50 days ahead for the busiest months.
The pick-up garage was once the stables and coach house of a Florentine palazzo, and the car waiting inside is a restored Cinquecento with the keys in it. That is where a Fiat 500 rental in Florence begins on this page: at the wheel of a vintage car, heading for the hills.
Four vintage Fiat experiences run from Florence, three with you driving and one with a private driver at the controls.
The Florence: Countryside Vintage Fiat 500 Driving Tour is the closest to a free set of wheels: five hours, a restored car, fuel, insurance, a guide in convoy and a ham and cheese tasting, all in one booking.
Three questions decide the rest: who drives, how long the day runs, and what the price already includes.
| Check | Why it matters | Our pick |
|---|---|---|
| Who drives | If the drive itself is the point, pick a self-drive; if the views matter more, a driver-led day works | You drive a restored 500 yourself, following a guide in convoy |
| Manual gearbox | Every vintage 500 here is a stick shift, and automatic drivers cannot take the wheel | Stick shift only, and the guide introduces the car before you set off |
| Duration | Short drives fit around a city day, long ones become the day itself | Five hours from the city outskirts into the Tuscan hills |
| What is included | Fuel, insurance and food quietly change the real cost of the day | Car, guide, two-way radio, fuel, both insurances and a ham and cheese tasting |
On every count the countryside drive covers the basics, so the price on screen stays close to the price you pay at the garage.

A modern hire car earns its keep on the autostrada, though it can feel small against crosswinds and passing trucks on a long run. A vintage 500 is a different instrument.
Its size makes it easy to place on winding Tuscan lanes, and its naturally slow pace turns the drive itself into the thing you came for.
The vintage car belongs in the hills. Florence's lanes are narrow and crowded with scooters, and historic centres run restricted-traffic rules, which is why every experience on this page leaves the city behind and keeps to quiet country roads.
| Countryside self-drive | Picnic convoy | Driver-led winery day | |
|---|---|---|---|
| Duration | 5 hours | 4 hours | 4 hours |
| Who drives | You, stick shift, guide leading | You, stick shift, in a colourful convoy | A private driver; guests never drive |
| Food and drink | Tuscan ham and cheese with a glass of Chianti | Three-course Tuscan lunch, wine and olive oil tasting | Multi-course farm lunch with Chianti wine and olive oil |
| Best for | Drivers who want the road itself | Food lovers who still want the wheel | Anyone who wants to taste freely |
Match the format to the day you have: two spare hours point to the short Chianti self-drive, and a full morning or afternoon buys the picnic or winery day. All three end back in Florence.


The day starts with a briefing, because a car from the 1960s has habits worth knowing. Then the convoy threads out of Florence along a cypress-lined avenue, with the red rooftops dropping away below.
What follows is the Chianti countryside at its postcard best: rolling hills, vineyards and olive groves, cypress trees standing in lines, old stone farmhouses on the slopes. The Chiantigiana road twists around hillsides and dips into small wooded valleys, passing compact hill towns with the fields close enough to touch.
Around Florence the route adds historic villas and castles scattered across the hills, and the stops are built for photos, with the car parked where the backdrop does the work.
At the garage, once a palazzo coach house
First views over Florence from the cypress avenue
The car parked with the city as your backdrop
Vineyards, olive groves and stone farmhouses
Short on time, the two-hour Chianti run covers the same idea
The shortest version of this day is the From Florence: Self-Drive Fiat 500 Tour in Chianti, two hours with a driving lesson included, so it fits a schedule that also wants museums or a long lunch.


The last car most visitors drove filtered the road through sensors and power steering. The 500 does the opposite: it feels smaller and lighter, and it tells you everything the surface is doing.
Steering at low speeds takes real effort, because there is no power steering, and the gearbox asks more attention than a modern one, with some original models needing double-clutching.
The hills add their own notes. Uphill the car can feel sluggish, and downhills put those old brakes to work. On narrow two-way roads you may meet a bus or a truck coming the other way, so the trick is patience and slow hands.
The tours are built around all of this: quiet secondary streets, an easy pace, and a guide in convoy with a two-way radio keeping everyone together. Long stretches rarely run past 40 mph, which is the point of the day.
You must be 18 or over, show a valid licence and genuinely handle a stick shift; the picnic tour wants a confident, regular manual driver
No power steering, a gearbox that takes attention, and hills that slow it down; the car communicates the road instead of hiding it
They belong on winding country lanes at an easy pace, and that easy pace is what you booked the day for
None of that makes the car hard; it makes the day slow in the best possible way, with the guide's radio close if a hill or a junction needs a second pair of hands.


This is the catch every wine lover meets. Italy's general blood alcohol limit is 0.5 g/L, with a zero limit for drivers in their first three years and for professional drivers, and above that limit the penalties can include a driving ban.
The tours split into two honest answers. The countryside driving tour includes wine tasting but requires a nominated driver, so whoever holds the keys stops at one glass.
The Florence: Vintage Fiat 500 Tour with Chianti Winery & Lunch goes the other way entirely: a private driver takes the wheel, guests are not allowed to drive, and everyone at the table can taste the Chianti and olive oils without a second thought.
One more honesty note: the self-drive tours are not driving lessons in the usual sense. The Chianti run includes a driving lesson on the double-clutch, but the countryside day expects you to arrive already comfortable with a manual gearbox.

October is the month to aim for: harvest colour on the vines, milder air for the open stretches, and crowds noticeably thinner than summer. The hills around the Chiantigiana look their best with the work of the vintage underway.
May brings spring green and wildflowers, which is why it is also the busiest month on these roads. September sits between the two, harvest season with peak-season crowds, so the views are generous and the roads are busy.
July and August run at full heat and full traffic, with the convoy format doing some of the work of keeping the day calm. Winter is the quiet season on the lanes, with the light gone early.
May: 5 out of 5 for how busy it gets. Spring color and long days come with some of Florence's highest visitor numbers.
Tap a month to read it.
Whichever month you choose, book it early; the busiest months sell out of restored cars first.
The paperwork is short but unforgiving. You must be at least 18 and hold a valid driving licence, and a Category B licence is sufficient for these vintage cars. Every self-drive tour on this page checks the same thing: the nominated driver can actually use a manual gearbox.
Non-EU licences need company. Americans can drive in Italy on a valid US licence as long as they also carry an International Driving Permit or a certified Italian translation, and the permit sits alongside the licence; carry the two together.
Italy accepts both the 1949 Geneva and 1968 Vienna permit types. EU licences travel without a permit, and UK photocard holders need none either, except those with an Isle of Man licence.
Sort the permit before you fly; it is the one document that can stop the day from starting.
Arriving as a non-EU driver without an International Driving Permit or certified Italian translation Arrange it at home before you fly, and carry it together with your licence on the day
With licence and permit in the same pocket, the paperwork is done and the day is yours.
The arrival itself is easy. The tram from Florence airport reaches the centre in about twenty minutes, which beats any argument with the city's traffic on the A1. Most visitors arrive this way and meet their vintage car on foot, keys in hand.
Florence's ZTL is the thing to respect. Cameras at every electronic gate read each plate, so an unauthorised vehicle earns a fine in the post without ever being stopped.
The zone runs Monday to Friday from 7:30 am to 8 pm and Saturday from 7:30 am to 4 pm, resting on Sundays and holidays, and from the first Thursday in April to the first Sunday in October the Thursday, Friday and Saturday nights are added.
If a hotel or garage inside the zone is part of your plan, hand them your vehicle details within three hours of entering or the fine follows. Garages outside the ZTL charge less anyway, and the walk in is short.
The countryside driving tour keeps the arithmetic simple: the restored car, fuel, third-party and driver insurance, the guide and the radio all sit inside the booking. What you see is close to what you pay.
The Chianti self-drive splits the difference. The driving lesson and the two hours on the road are in the price, and a fuel surcharge is settled separately, so carry a little cash or card for the end of the day.
That same tour asks for a credit card at the start for insurance purposes, which is standard for vintage cars.
On the winery lunch tour the structure changes again: pricing works per car, so a couple or two friends split one day between them, and the farm lunch, wine and olive oil tastings are all included.
Gratuities sit outside every tour here, and worth remembering is what is never billed on the countryside drive: no deposit to chase and no fuel receipts to collect.
The rhythm of these bookings runs slower than most city plans. For the busiest travel months in Tuscany, book about 50 days ahead to hold a spot; the restored cars are few and the convoys fill from the front.
Food and wine days follow a different clock. Around Florence and in Chianti, two to four weeks ahead is enough in ordinary weeks, but during harvest the popular wineries fill quickly and the picnic and winery tours go with them, so plan those dates early.
The drive you really want on the day you really want needs the longest lead time, and the day that flexes can be booked later. Summer dates and weekend convoys sit at the strict end of the scale; a midweek October run is the forgiving end.
Every Florence tour on this page carries the same term, which is the reason you can commit to a date without holding your breath: cancel up to 24 hours in advance for a full refund. Plans move, flights shift, and this clause is what makes booking early feel safe.
| If this happens | What happens then |
|---|---|
| Plans change more than a day ahead | Cancel for a full refund, on every Florence tour on this page |
| You want a different date instead | Cancel free up to 24 hours ahead and rebook the day that suits |
| Inside the last 24 hours | The refund window has closed, so book the date you can genuinely commit to |
Inside that final day the terms have nothing on offer, which is the one place to be careful with a tight itinerary. Build a little buffer before the meeting time, arrive with the licence in the right pocket, and the day runs itself from there.
A Fiat day leaves room around it, and the other tours here slot in without competing. The two-hour Chianti self-drive pairs naturally with a morning in the city: it is short, it includes the driving lesson, and it returns you with the afternoon intact.
The five-hour countryside drive owns most of a day, so the honest pairing is the evening: dinner in Florence and an easy walk afterward. If the weather or your legs argue for a slower day, the driver-led winery lunch asks nothing of you but appetite, four hours door to door.
One drive and one slow day works better than two drives back to back. The hills are the same hills, and the picnic and winery days give you the vineyards from a lunch table, with the same views outside.
Two hours teaches you the double-clutch and leaves the day for everything else Florence does well
A line of bright vintage 500s on a quiet Tuscan road turns heads at every village
Whichever pairing you pick, book the drive first and let the rest of Florence fill in around it.
Very well run tour, vehicles in excellent condition. Instructions and a quick driving test made sure we were comfortable. Leo was helpful and entertaining, lunch was tasty. We all loved our day, highly recommend!
Take the Florence: Countryside Vintage Fiat 500 Driving Tour if you can drive a manual and want five unhurried hours in the hills, with fuel, insurance and lunch-time tasting sorted.
Choose the picnic or winery day for food, the two-hour Chianti run for a tight schedule, and the driver-led tour if you would rather taste the Chianti than change its gears.

Quick answers on driving a vintage Fiat 500 from Florence, from licences and gearboxes to wine stops.
Florence2026The closest options on sale here are self-drive tours that include the car. The five-hour countryside driving tour includes the rental of a restored Fiat 500 for the whole route, and the two-hour Chianti drive puts you behind the wheel after a short lesson.
The Florence drives listed here run in classic Cinquecentos with fixed roofs, so no open-top version is part of these tours. What you get instead is the drive itself: quiet country lanes, cypress-lined avenues and viewpoints over the Chianti hills from a restored 1960s car.
Yes. Every self-drive option requires a driver comfortable with a stick shift, and automatic drivers cannot take the wheel. The two-hour Chianti tour starts with a driving lesson that covers the double-clutch before you set off.
Bring a valid full driving licence. Non-EU citizens also need an International Driving Permit carried alongside the licence, so sort that out before you fly. The Chianti self-drive tour also asks you to bring a credit card for insurance purposes.
Drivers must be at least 18, which matches Italy's legal minimum for driving a car. The five-hour countryside tour and the two-hour Chianti drive both state this in their booking terms.
You can pick the length that suits the day. The Chianti self-drive runs two hours, the picnic tour takes four, and the countryside driving tour lasts five, ending back in Florence. Each leaves time for photo stops along the way.
It takes more attention than a modern car: no power steering, a gearbox that can demand double-clutching, and brakes that work hard on downhill stretches. The routes use quiet secondary streets at a relaxed pace, a briefing covers the car before you start, and the guide travels in convoy with a two-way radio.
On the five-hour countryside tour, each car takes up to three adults, or two adults and two children aged 3 to 12 who travel free. One thing to plan around: the rear seats have no safety belts fitted.
The five-hour tour includes a glass of Chianti with the ham and cheese tasting, so keep it to one glass. If you want a proper winery lunch with several tastings, the four-hour Chianti tour brings a private driver instead, so nobody in your car drinks and drives.
The routes wind through Chianti country: rolling hills, vineyards, olive groves, cypress-lined roads and old stone farmhouses. The picnic tour stops at a 13th-century castle and a hilltop viewpoint over Florence's red rooftops, and the countryside tour pauses at one of the city's oldest churches.
Not on these tours. The guide leads you out of the city and onto quiet country roads, so the historic-centre ZTL rules that trap rental drivers never come into play. Your drive starts at a garage in Florence and returns there.
All four Florence tours on this page let you cancel up to 24 hours in advance for a full refund. That gives you room to book early and still adjust if your itinerary shifts.

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Five hours behind the wheel of a restored vintage Fiat 500 through the Tuscan hills, with fuel, insurance and free cancellation up to 24 hours ahead.