811Drive a restored Cinquecento out of Florence and into the Chianti hills. Follow a guide in convoy through cypress-lined lanes, stop for Tuscan ham and cheese with a glass of Chianti, and see the countryside the way the cars of the 1960s were built for. Pick your route and book your car today.
Florence has two ways to meet the Cinquecento. You can take the wheel yourself and follow a guide into the Tuscan hills, or sit back while a local drives and narrates. Drivers need a manual gearbox and a licence; everyone else can simply enjoy the view.
If you normally drive an automatic, pick one of the driver-led tours instead, where a private driver handles the car. Before booking a self-drive option, check that your licence is valid and that the nominated driver in your group can handle stick-shift gears on hilly roads.
The longest outing at five hours, with ham and cheese tasting and radio contact with your guide, and a 4.9 rating from over 300 reviews.
Just two hours at the wheel, with a driving lesson and a credit card for insurance, at 4.9 stars from 20 reviews.
A private guide drives a vintage yellow electric cabrio, taking photos at every viewpoint, rated 4.9 by 89 travelers.
A private driver takes you to a family-run winery for a multi-course Tuscan lunch, with a 5-star rating across 27 reviews.
The five-hour countryside driving tour puts you behind the wheel of a restored Cinquecento, with a guide in radio contact the whole way. You leave Florence through a cypress-lined avenue, follow quiet country lanes past vineyards and stone farmhouses, and stop for photos where the rolling hills open up.
The day ends on a private terrace with Tuscan ham, cheese and a glass of Chianti. Fuel, insurance and the car itself are all included, so the only thing to bring is a valid licence and a willingness to work a stick shift.
Green marks the lowest price. Prices per person.
Perfect escape from the city! Met so many friendly people, our guide was wonderfully warm.
Amazing half day with Leo and Antonio, supportive, informative, great vibes, well planned. The old cars have quirks but you're led from the front.
Bella was energetic, met us early, even toured the olive mill first. Five cars, tops down, fresh air, gorgeous views and stops. Light lunch was great, took wine home.
The convertible Fiats were perfect for our family of 5 exploring Florence's scenic edges, best views! Worth every penny to Fiesole and Piazzale Michelangelo. Felt spoiled, learned so much history and culture.
Most fun tour ever. Gorgeous views, such fun cars.
10/10! Taxi trouble, but our guides were so accommodating and friendly, they even helped my fiancée pull off a surprise proposal, day-of! Nino and Christina are unforgettable. <3
Gabriel was an excellent guide, knowledgeable, fun, and clearly proud of his country. Lunch was honestly just ok, but the views and wine more than made up for it.
Most reviewers name their guide as the reason the day worked, patient with the clutch and full of local stories.
Several travelers did not expect strangers to wave, honk and photograph the little car all the way round the hills.
A few wished the ride lasted longer, or that they had shared the driving with someone else.
Choose a date first, then compare the tour options listed for it. The countryside drive runs about five hours, the wine tours three, so pick one that fits the day you have.
Decide whether you want to drive yourself or ride with a driver. Self-drive tours need one nominated driver; the winery and Chianti lunch tours provide a private driver instead.
Confirm the driver is at least 18, holds a valid driving licence and can use a manual gearbox. Non-EU visitors should also carry an International Driving Permit.
Reserve your slot and arrive early for the briefing on driving the vintage car, which is part of the schedule. Add buffer time before any train or flight afterwards.
Pack comfortable shoes, sunglasses and a hat, and dress for the weather since some routes run rain or shine. Leave bulk bags at your hotel, as the cabin is snug.
Every Florence tour works one of two ways. On the countryside, sunset and picnic tours you take the wheel yourself, following a guide. On the winery tours, the Chianti lunch tour and the electric city tour you ride as a passenger with a driver or guide.
The city tour in the electric Fiat 500 is private, just you and your guide. The self-drive countryside tour runs as a convoy, with cars in radio contact with the guide. The Chianti lunch tour prices per car and seats two guests plus the driver.
The self-drive countryside tour covers most of what the day needs, but a few things sit outside the price. On the page:
Florence food and wine outings fill quickly, and during the autumn harvest popular wineries fill faster still. Book two to four weeks ahead for those, and earlier in high season if you want a specific date and time.
Florence outings run from about 90 minutes to six hours, so leave buffer after the tour for the briefing and any tasting, which are part of the schedule. The sunset tour runs rain or shine. If you plan to self-drive into the historic centre, remember the ZTL cameras there fine unauthorised plates.
A change of plan costs you nothing if it comes early. All of the Florence tours refund in full when you cancel at least 24 hours ahead, and the electric city tour uses that same window to help you reschedule after heavy rain.
On self-drive tours you must be able to use a stick shift, and the nominated driver presents a valid licence at the start. Drivers must be 18 or older. The wine tasting tours do not let guests drive at all, so you can taste freely.
The vintage cabin is snug. Two of the Florence tours turn away people over 200 cm and those with back problems, and the countryside cars have no belts fitted in the rear seats, so check the limits for children on the tour you pick.
Some tours pick you up and some do not. The electric city tour collects you at a meeting point you choose in advance, while the countryside driving tours start at a garage in Florence. Check before you book, since a few leave you to arrive on your own.
You get photos without lifting a finger on some tours. The electric city tour has your guide shooting at every viewpoint, and the countryside driving tour builds in photo stops at the church, the cypress avenue and the overlooks over the rolling hills.
Florence is the city where you can drive a 2.97-metre piece of Italian history into the hills the Renaissance shaped. Which format fits your trip, and how early you book, decide how good that day turns out.
Book about 50 days ahead for the busiest months, and 2 to 4 weeks ahead for a harvest-season wine outing.
You need a manual licence to drive; non-EU drivers also need an International Driving Permit carried with their licence.
Every main Florence tour lets you cancel free up to 24 hours before, so book early and change later if you must.
A few minutes after you leave the garage, the question answers itself. The Cinquecento, as Italians call it, is 2.97 metres long, rear-engined and rear-wheel drive, and it carries you at a pace where the drive itself is the experience.
The hills around Florence were shaped for exactly this speed. Renaissance-era landowners laid out the roads, farms and cypress lines to make the countryside look orderly from a carriage or a slow car, and hilltop farmhouses still stand where they can be seen across the fields.
So yes, if you want the countryside and the wheel to be the whole point of the morning. A vintage Florence day rewards people who like driving as much as the views.
It has no power steering and an unsynchronized gearbox, so it asks more attention than a rental
It is made for winding country roads at a slow pace; long highway runs feel tiring
The vintage Nuova 500 is rear-engined, rear-wheel drive and 58 cm shorter than the modern one
If those rows change your picture of the car, the driver-led tours keep the hills and the views and hand the gears to someone else.
The day on the Florence Countryside Vintage Fiat 500 Driving Tour has a shape you can picture before you book. It starts in a garage that was once the stables of a Florentine palazzo, where a guide walks you through the quirks of a 1960s car until you feel confident with it.
Then the convoy sets off. The rule of the day is quiet secondary roads at a relaxed pace, radio contact with the guide the whole way, and stops whenever the light earns one.
The Chiantigiana road twists around hillsides and dips into small wooded valleys, passing compact hill towns with vineyards, olive groves, cypress lines and old stone farmhouses close by.
You practise until confident
First stop at one of Florence's oldest churches
Cars travel at a relaxed pace
Included, with a glass of Chianti
The rhythm, more than the itinerary, is what people remember: short stops, slow bends, and a terrace at the end.
Four formats, four different days. The wheel decides the first split: on the self-drive countryside tour you follow a guide in convoy; on the driver-led tours you never touch the wheel, which also means everyone can taste the wine.
If photos and hills matter more than driving, the Florence Private City Tour in a Vintage Electric Fiat 500 puts you in a sun-yellow cabrio with a local guide who takes pictures at every viewpoint, with no other group in the car. It runs 90 minutes or three hours, the longer version climbing to Fiesole.
Food lovers have two further paths: a wine-and-lunch tour with a private driver through Chianti Classico, or a self-drive picnic day in Tuscany with a three-course lunch.
Chianti is steep, vine-terraced hill country around medieval castle villages, and a Val d'Orcia route swaps that for a picnic at a pecorino farm, in a wider and gentler landscape further south.
| Private electric city tour | Countryside driving tour | Winery and lunch tour | |
|---|---|---|---|
| Who drives | Guide drives, you ride | You drive, guide leads convoy | Private driver drives |
| How long | 90 minutes to 3 hours | 5 hours | 2 to 4 hours |
| Food | None | Tuscan ham and cheese tasting | Tuscan lunch with wine and olive oil |
| Crowds | Private, no fixed groups | Small convoy | Private car, up to 2 guests plus driver |
| Suits | Photos, hills, comfort | Drivers who want the road | Wine lovers who want to relax |
Use the rows as a filter. Decide first who drives, then how much of the day the meal should take, and the right tour is usually the one left standing.
Timing decides two things at once: the light you drive in and whether a car is left for you. In the busiest months, book about 50 days ahead to be sure of a spot.
Wine outings run on their own clock. Chianti wineries fill quickly during harvest, so a food or wine tour needs 2 to 4 weeks of lead time, and popular wine estates fill first.
The sunset tours depart in the late afternoon from April through October, which is when the day's best light and the tour schedule overlap; from November the departure options thin out sharply.
June: 5 out of 5 for sunset. 8:57 pm
Tap a month to read it.
April: 5 out of 5 for 5 pm tour departure listed. Listed by one tour operator.
Tap a month to read it.
The pattern points one way. Aim for late spring or early autumn if you can, lock the date in early, and treat summer weekends as dates that sell out long before the week you book.
The honest answer to the wine question: Italy's blood alcohol limit is 0.5 g/L for most drivers, and zero for anyone in their first three years of licence. If you are the nominated driver on a self-drive day, the practical rule is one glass, no more.
The cleaner way out is to pick a format where you never drive. On the Florence Vintage Fiat 500 Tour with Chianti Winery & Lunch a private driver handles the car, so the whole table can taste Chianti and the olive oil alongside a multi-course Tuscan lunch at a family-run farm.
Guests are simply not allowed to drive on it, and Italian law means you sign a short rental agreement before setting off so the insurance covers you as a passenger.
Dietary needs work best when they are flagged at booking time. Some countryside tours offer a vegetarian option but cannot handle gluten-free or other alternative diets, while winery kitchens can often adapt menus for vegans and allergies if you tell them when you reserve, so the kitchen can plan.
Florence is an easy city to arrive in without a car, which is exactly what you want on a day you spend behind the wheel of someone else's classic.
Amerigo Vespucci airport sits about 20 minutes from the central Santa Maria Novella station on the T2 tram, with last services near midnight on most nights and later on Fridays and Saturdays.
By train, Pisa is a 90-minute trip with a short shuttle connection, Bologna is direct in about 35 minutes, and Milan runs direct in roughly an hour and 40 minutes. From central Florence, the Scandicci meeting point for the sunset tour is a short taxi hop.
Whichever way you come, build the connection time into the day. The countryside tours start from a garage in the city, and a missed briefing means a missed car.
Self-drive is the format people underestimate, so here is the whole picture.
Drivers must be at least 18 with a valid licence, and manual experience is not negotiable: automatic-only drivers cannot take the wheel on these tours, and a briefing on the vintage car comes before you set off because it is not a driving lesson.
Documents follow the rules. A Category B licence is enough for a vintage car, EU licences travel as they are, UK photocard holders need no extra permit, and non-EU citizens must carry an International Driving Permit together with their national licence.
What the car itself feels like matters too. There is no radio, no air conditioning, no power steering, and on some models an unsynchronized gearbox that needs double-clutching. It is smaller and lighter than anything modern and tells you far more about the road.
Read the middle row against yourself. If you change gears in traffic without thinking, the self-drive tour is yours; if the word clutch makes you pause, the driver-led formats give you the same hills with none of the paperwork.
Florence fines by camera, so the ZTL is worth two minutes of attention. The historic-centre zone runs Monday to Friday from 7:30 am to 8 pm and Saturday from 7:30 am to 4 pm, staying quiet on Sundays and holidays.
From the first Thursday in April to the first Sunday in October, the hours stretch into Thursday, Friday and Saturday nights too.
Electronic gates read every plate that crosses, and unauthorised vehicles are fined automatically. If your hotel sits inside the zone, hand the facility your vehicle details within three hours of entering or the fine stands. Street parking inside the ZTL is not allowed at all; garages outside the zone cost less anyway.
The same logic holds in the Chianti villages. Monteriggioni's castle zone bars unauthorised vehicles from driving and parking at all times, and Castellina in Chianti restricts its historic centre on authorisation grounds.
The simple version: park outside the town, walk in, and let the tour handle the roads it knows.
A vintage 500 is a small 1960s car, and the honest answer is that comfort depends on you.
Operators list people over 200 cm and guests with back problems as unsuitable, and travelers who have spent real time in these cars say discomfort tends to set in above about 1.85 m, or 6 ft 1 in.
The rear seats carry no safety belts on the self-drive countryside cars, which is worth knowing before you plan who sits where. On the driving tour, each car takes up to three adults, or two adults with two children aged 3 to 12 riding free.
Tall drivers can manage, but long stretches in the cabin get tight
For hours in the hills, plan the seating around that
It is part of the vintage charm, and part of what some guests hand back
None of this is a reason to skip the day. It just makes the choice of format worth weighing against your own height and back before you commit.
The practical planning note is about time more than luggage. A Florence outing runs from about two hours to about six depending on the tour, and the safety briefing and the tasting are part of the schedule, not extras squeezed around it.
That means the block you protect in your diary is longer than the tour's headline duration. A short city ride still needs the meeting, the introduction to the car and the walk back, and a countryside day with lunch can swallow most of an afternoon.
Book onward travel, trains and flights, around the whole block, never around the stated two hours.
As for luggage, comfortable shoes cover most stops, and a camera earns its place. Everything else the car itself provides, mostly by not having it.
The booking risk on these tours is low, and it is worth saying plainly before you click. The main Florence tours, the countryside drive, the wine-and-lunch outing and the sunset tour, all allow free cancellation up to 24 hours ahead for a full refund.
That changes how you should book. In a peak month or around harvest, when cars and wineries fill weeks ahead, the right move is to reserve early for the date you want and cancel without cost if the trip shifts. Waiting until you are certain is the way to lose the date.
| If this happens | What happens then |
|---|---|
| Cancel up to 24 hours before | Full refund on the countryside, wine-lunch and sunset tours |
| Plans change within 24 hours | No refund, so treat that window as committed |
| Weather or the operator cancels | An alternative date or refund, per each tour's own terms |
Check the exact window on the card of the tour you pick, since terms can differ, but the 24-hour rule holds across the Florence line-up.
Once the drive is booked, the day has edges worth filling. Greve in Chianti's main food market runs on Saturday mornings only, so if your tour lands on a Saturday, arrive early and eat your way through the square before the convoy leaves.
Wineries keep their own clocks. Rural estates can close one day a week, and from late November to February many cut their opening days or ask for advance booking, so a winter wine stop needs a check before you plan the afternoon around it.
The rest builds itself. San Miniato al Monte and the panoramic hills give you views over Florence on the way out, the Fiesole climb adds an ancient hilltop town for anyone with a spare three hours, and a late return leaves the evening for the city.
Treat the drive as the spine of the day and the food and viewpoints as the reason the schedule works.
The convertible Fiats were perfect for our family of 5 exploring Florence's scenic edges, best views! Worth every penny to Fiesole and Piazzale Michelangelo. Felt spoiled, learned so much history and culture.
A vintage Fiat 500 day around Florence earns its slot when the countryside and the car are the point of it.
Pick self-drive if you can handle a manual gearbox and want the road, pick a driver-led wine or city tour if you want everyone free to taste and photograph. Book early, cancel free up to 24 hours out, and check your height against the car before you commit.
Short answers to what Florence-bound readers ask most before choosing their Fiat 500 outing.
Florence2026For the self-drive countryside tour, yes. Drivers must be comfortable with stick-shift gears, and the guide briefs you on the car before you set off. If you only drive automatic, pick one of the driver-led tours instead and ride as a passenger.
Bring a valid driving licence, and drivers must be at least 18. If your licence is from outside the EU, carry an International Driving Permit alongside it. EU licences are fine on their own.
For the food and wine outings in Florence and Chianti, plan about two to four weeks ahead, because harvest-season winery visits fill quickly. Popular dates in general reward early booking, and all the tours here allow free cancellation up to 24 hours before.
Several of the Florence tours run rain or shine, so a grey sky does not end the day. On the private electric city tour, heavy rain is the one case that leads to rescheduling, and the 24-hour free cancellation covers you either way.
A vintage 500 is snug. Some Florence tours list people over 200 cm, about 6 ft 6 in, as unsuitable, and riders around 6 ft 1 in often find it tight. If you are tall, the private city ride with more room to settle in may suit you better than a long countryside stretch.
On the winery tours you are not allowed to drive at all; a private driver handles the car so everyone can taste. The self-drive countryside tour keeps the wine to a glass with the ham and cheese stop, since the nominated driver stays behind the wheel.
Yes, with limits. The countryside driving tour takes two children aged 3 to 12 free of charge alongside two adults, while the private electric city tour does not take children under 3. Check the age rules on the tour you have in mind before you book.
The countryside driving tour offers a vegetarian option but cannot cover gluten-free or other alternative diets. If you have a dietary restriction, mention it to the tour operator when you book so they can tell you what is possible.
The private electric city tour includes pickup from designated meeting points you choose when booking. The countryside driving tour and the winery tours do not include hotel pickup, so plan to reach the starting point in central Florence yourself.
Comfortable shoes are the one thing every Florence tour asks for, since you will walk at the stops. Add a hat, sunscreen and a camera for the open-top city ride, and keep a light layer handy for the hills after sunset.
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Five hours at the wheel, a guide on the radio, ham and cheese with Chianti on a terrace. Cancel free up to 24 hours before.
