837Drive a vintage Fiat 500 through Tuscany's quiet lanes, vineyards and hill towns, with wine or food along the way. Book the countryside outing that fits your trip - self-drive it yourself in convoy with a guide, or ride with a private driver to a Chianti winery for lunch. Full refund if you cancel up to 24 hours ahead.
Tuscan Fiat 500 outings come in two main shapes: you take the wheel yourself on quiet country roads, or a driver and guide handle everything while you ride and taste. Driving yourself suits confident manual drivers who want the vintage car to be the point; a guided or chauffeured ride suits anyone who would rather spend the day on wine, views and photos.
Bring your national licence and your IDP or a certified Italian translation on the day, and if you hold a UK photocard licence you can drive in Italy without the permit.
A five-hour countryside drive you steer yourself, with ham and cheese and a glass of Chianti included at the end.
The shortest outing on this page, and it runs on fuel already paid for, so nothing extra to plan.
A private driver takes the wheel through Chianti Classico, so the whole group can taste without counting glasses.
A yellow vintage cabrio with room to breathe, plus a three-hour climb to Fiesole for the hilltop views.
The first thing worth the price is the view through a cypress-lined avenue as the hills of Tuscany open up, with your own restored Fiat 500 humming underneath you. This five-hour drive from Florence puts you behind the wheel on quiet country lanes, always in convoy with a guide who stays on the radio.
Between the photo stops you get a terrace overlooking the rolling hills, a plate of Tuscan ham and cheese, and a glass of Chianti. Fuel and insurance are included; hotel pickup is not.
Green marks the lowest price. Prices per person.
Highly recommend escaping the city for this.
Unforgettable! We rented a gorgeous vintage Fiat 500 for a Tuscan aperitivo at a vineyard with km0 products: magical atmosphere, stunning views, iconic car.
Amazing experience with wonderful guides Leo and Antonio, supportive, informative, great vibes. Well planned, packing lots into half a day.
Bella was energetic and even had us tour the olive mill early. Driving the vintage cars was a blast once you get used to them.
Wonderful guides! The convertible Fiats were perfect for our family of 5 exploring Florence's scenic edges, best views.
Most fun tour. Gorgeous views, fun cars, and Bella and Edoardo were knowledgeable hosts on wine and EVOO production. Stunning winery with fascinating family history.
10/10!! Taxi trouble, but our guides were accommodating and the friendliest ever. They helped my fiancée pull off a day-of surprise proposal, perfect and so special. Nino and Christina, we'll remember you forever!
Their guide made the drive, walking them through the old car before the hills and staying patient the whole way.
Several visitors did not expect how many people waved and honked at the little cars on the road.
Many reviewers wished the ride lasted longer, and a few said the tasting portions could have been more generous.
Choose a date and time that leaves room in your day, because the countryside driving tour runs about five hours. Weekend slots in the busy months fill first.
The countryside driving tour has a single option, so the real choice is between tour styles on this page: self-drive with ham and cheese tasting, or guided rides with wine and lunch.
After payment you get a confirmation with the meeting details, and the operator may message you through the booking platform with anything extra. Read those messages before the day.
The countryside driving tour starts from a garage in central Florence, once the coach house of a palazzo, and there is no hotel pickup. Show the voucher on your phone and arrive a little early to meet the guide.
Wear shoes you can drive in and get to the meeting point with time to spare. The guide briefs you on the car, hands out the two-way radios, and the convoy sets off through Florence before the cypress-lined road into the hills.
Most of these tours start from a set meeting point in Florence, and you get there on your own. The private electric Fiat tour is the exception: it picks you up at a meeting spot you choose from its listed locations, and the operator tries to accommodate special requests.
You choose the format. On self-drive outings you follow a guide in convoy or a mapped route, and the driving itself becomes part of the day on quiet country roads. On the Chianti winery tours and the electric Florence tour a professional driver takes the wheel, so you can taste the wine freely.
The countryside driving tour fits up to 3 adults, or 2 adults with 2 children aged 3 to 12 in one car. The Chianti winery tours carry 2 guests plus the driver, and price is set per car. The electric Florence tour is private, just you and your guide.
The five-hour countryside drive covers the car rental, fuel, third-party and driver insurance, a two-way radio to stay in touch with the guide, and a Tuscan ham and cheese tasting with Chianti. The Chianti winery tours include lunch or appetizers plus wine and olive oil tastings.
A few things sit outside the booking. The wine-and-lunch tour collects a fuel surcharge per car on the day, and tips for guides are optional and at your discretion. Bottles of wine or olive oil you buy at the winery are yours to pay for, though shipping home is sometimes available.
For food and wine outings around Florence and Chianti, book roughly two to four weeks ahead. In harvest season the popular wineries fill quickly, so earlier is safer if your trip falls between late September and October.
Every tour on this page can be cancelled up to 24 hours in advance for a full refund, so a change of plans the day before costs you nothing. The electric Florence tour uses that same free window to help you reschedule if heavy rain rolls in.
Bring your driving licence to every self-drive tour. EU licences work on their own, and UK photocard holders do not need an International Driving Permit in Italy. Non-EU drivers must carry an IDP alongside their national licence; it supplements the licence, it does not replace it. Some tours also ask for a credit card.
The sunset wine tour runs rain or shine, so check the forecast and dress for what is coming, with a layer you can add or shed. One more thing to weigh: after a sunset picnic the drive back happens in the dark, which some drivers find is part of the adventure.
Wear comfortable clothes that let you move easily, and shoes suited to uneven ground near farms and wineries. Sunglasses, sunscreen and a camera earn their place, and a light jacket covers the wind on an open road. Drivers bring their licence, plus a credit card where requested.
The winery tours decline pregnant women, people with back problems, and anyone over about 200 cm, because the cabin is tight. The electric Florence tour excludes wheelchair users and children under 3. Check the tour page for the limits on the specific experience you pick.
Vintage Fiat 500s have manual gearboxes, and the wine-and-lunch tour flatly rules out automatic drivers at the wheel. These drives are not lessons: the nominated driver has to be comfortable with a stick shift before setting off.
A restored Cinquecento, quiet Chianti roads and a glass of wine at the end: Tuscany was made for this little car. It asks in return for a manual gearbox and a bit of planning, and the right route rewards both.
Book the busiest months about 50 days ahead; harvest wine outings need two to four weeks.
You must be able to drive a manual car, or choose a tour with a private driver.
Every Florence tour here refunds in full if you cancel up to 24 hours before the start.
A restored Cinquecento idles at the edge of a cypress-lined avenue, engine buzzing like a sewing machine, and the hills ahead belong to no schedule.
On winding Tuscan country roads the little car comes into its own, small enough to place exactly where you want it, with a pace that turns the drive into the sight itself.
The car tells you everything a modern one filters out. There is no power steering, so low-speed turns take muscle, and the gearbox wants more attention than a modern car's; some original models carry an unsynchronized gearbox that asks for double-clutching.
On a motorway all of this turns tiring. On a quiet country lane it becomes the point.
Self-drive tours require the nominated driver to be comfortable driving a manual car Automatic-only drivers cannot take the wheel on these tours, so pick an outing with a private driver instead
There is one honest catch, and you meet it before you reach the road. Book a self-drive date only if the nominated driver can handle a manual car, since the briefing on the day is a refresher only. Ride as a passenger with a driver-guide and the same roads still pass your window.
The morning starts in a Florence garage that was once the stables and coach house of a palazzo. A restored Fiat 500 waits there, and the guide walks the nominated driver through the car's habits before anyone turns a key: clutch travel, gearing, hill starts.
A briefing covers the vintage gearbox before you set off
A two-way radio keeps every car in touch with the guide
The guide sets a relaxed pace through the Chianti hills
An early stop at one of Florence's oldest churches
A vegetarian option exists, gluten-free does not
Fuel and insurance are included in the day
Then the convoy rolls out and into the hills. The Florence: Countryside Vintage Fiat 500 Driving Tour runs five hours at a relaxed pace on quiet secondary roads, with the guide in radio contact the whole way. Fuel, third-party and driver insurance, and a ham-and-cheese stop with Chianti are all included.
Stops come often: a viewpoint over Florence early on, photo sessions with the car itself, villages where the lanes are barely wider than the car. Keep the tasting to a single glass if you are the driver. Italian law allows 0.5 g/L for most drivers, and the ride home on country roads deserves full attention.
Chianti is the postcard most people carry in their heads: steep, vine-terraced hills and medieval castle villages. The Chiantigiana road twists around hillsides and dips into small wooded valleys, and the villages sit close enough together to walk between after a tasting. If your Tuscany picture has vines on every slope, start here.
Val d'Orcia holds a Renaissance rural landscape where farms, fields and cypress rows grew up together with the land around them.
The Val d'Orcia: Fiat 500 tour with picnic at a Pecorino cheese farm gives it five hours, with petrol and third-party insurance included, a local guide leading, and room for up to three guests per car or four in a Fiat 600.
The hill towns around San Gimignano and Volterra bring the surprises. A manual 500 finds uphill starts a genuine challenge, and a drive back after a sunset picnic becomes an adventure in the dark. If medieval streets are the draw, set your departure hour by the light, because the drive back runs late.
Three formats, really. On a guided convoy drive you operate the car yourself and follow the guide by radio. On a private-driver outing someone else handles every road. On a rental you go alone. The difference shows most clearly over lunch.
| Guided drive you operate | Ride with a private driver | Self-drive rental | |
|---|---|---|---|
| Who drives | You, with the guide leading by radio | A professional driver, guests never take the wheel | You alone, on your own route |
| Duration | 5 hours on the Florence countryside drive | 4 hours to a Chianti winery lunch | Half a day or more |
| Food and drink | Tuscan ham and cheese with Chianti | Multi-course lunch, Chianti wine and olive oil | Whatever stops you plan |
| Included | Fuel, third-party and driver insurance, two-way radio | Car, driver, wine and oil tastings | Usually fuel and a mileage allowance |
| Best for | Drivers at ease with a manual gearbox | Passengers, nervous drivers, wine tasters | Confident drivers who want freedom |
The Florence Wine Tasting and Tuscan Lunch in a Vintage Fiat 500 sits in the middle of that table: three hours, a professional guide, car hire and standard insurance, ending with a light Tuscan lunch and wine tasting at a Renaissance-era villa's vineyards.
The nominated driver must drive a manual regularly, and an automatic driver cannot take the wheel.
Two cautions before you shortlist. The Chianti outing with a professional driver carries at most two guests per car, booked as a whole car.
And the cabin itself: travelers around 6 ft 1 in and taller find a vintage 500 increasingly uncomfortable, and people who spend real time in them describe it as essentially a two-person car.
High season moves the calendar before it moves the car. The busiest months sell out around 50 days ahead, so a July or September date wants booking in late spring, while the departure hours are still open.
Wine and food outings run on a shorter clock but a sharper one: two to four weeks ahead. Harvest-season winery visits fill quickly, so the weeks when the grapes come in are the best and the busiest at once.
Sunset drives need the daylight worked backwards. A three-hour outing that ends at a winery at dusk must start with enough light left for the winding roads out, and the drive home after dark on unfamiliar hills is part of the deal if you plan for it.
Book the earlier departure in late spring, when the evenings still shorten quickly.
Most Fiat 500 tours in Tuscany start in Florence, and the first hour of the day decides whether it begins calmly. From Amerigo Vespucci airport, the T2 tram runs direct to the city centre in about 20 minutes, with no parking to think about at either end.
Driving in takes far longer, about an hour and 37 minutes by the usual estimate without traffic, and it lands you in a city built to discourage cars. For a morning tour start the tram wins; save your driving for the hills.
Whichever way you come, arrive with minutes to spare rather than seconds. The briefing on the car happens at the meeting point, and the convoy leaves when it leaves.
Florence's historic centre sits inside a restricted-traffic zone, and electronic gates photograph every plate that crosses.
The ZTL runs Monday to Friday from 7:30 am to 8 pm and Saturday from 7:30 am to 4 pm, goes quiet on Sundays and holidays, and stretches into Thursday to Saturday nights from the first Thursday in April to the first Sunday in October.
There is no parking on the street inside the zone, and garages outside cost less than those within. If a hotel or garage inside the ZTL is your destination, hand over the car's details within three hours of entering, or a fine follows anyway.
Size changes nothing, the gates fine every unauthorised plate automatically
Registration goes through the property, and even then it may not cover parking
Cameras record each entry, so the notice arrives long after the trip
The same logic holds in the Chianti towns you may pass through on your own. Monteriggioni's castle zone bars unauthorised cars at all times, and Castellina in Chianti restricts its historic centre by authorisation. Park outside the walls and walk in; the towns are small, and the walk is the pleasant part.
The paperwork is simpler than it looks. A category B car licence is enough to drive a vintage 500, and the Florence countryside driving tour asks every nominated driver for a valid driving licence, a minimum age of 18 and comfort with a manual transmission.
Where you come from decides the extra page. EU licences work on their own, and UK photocard holders do not need a permit to drive in Italy. Non-EU drivers must carry an International Driving Permit alongside their national licence, and the permit supplements the licence rather than replacing it.
For rentals, bring an identity document and a credit card in the driver's name, and expect operators to want a licence held for at least a year.
On cover: the countryside drive includes third-party and driver insurance, which is the legal baseline plus a little more. All of this takes ten minutes to verify, and it is worth doing before you pay, not at the meeting point.
An old car with an open roof hands the day over to the weather. Sun lands on your face for hours, wind arrives at speed, and the shade at a winery can feel suddenly cool. Dress in clothes that move easily and keep a layer within reach that you can add or take off.
Shoes matter more than outfits. Stops involve gravel, farm tracks and uneven ground near vineyards, so closed shoes beat sandals. Add sunglasses, a hat that stays on at speed, sunscreen and a camera; the guide stops where the light earns a photograph.
Families should look at the seating before booking. The rear seats on the countryside drive carry no safety belts, each car takes up to three adults or two adults with two children aged 3 to 12 riding free, and belts are compulsory wherever a seat has one fitted.
Plan changes cost nothing if you catch them a day early: cancellation up to 24 hours in advance brings a full refund on the Florence tours, covering the delayed flight, the sick child and the changed mind.
| If this happens | What happens then |
|---|---|
| Cancel up to 24 hours before the start | Full refund on the Florence tours |
| Severe weather on the day | Rescheduling, subject to the dates the operator still has free |
| Plans change inside 24 hours | No refund, the 24-hour mark is the cutoff |
| A date you cannot pin down yet | Book the day you expect, then cancel free a full day ahead if it wobbles |
Weather plays by its own rules beside that. Several of these outings run rain or shine, including the sunset drive, though severe conditions can push the date back subject to availability. Light rain rarely stops a roofed Cinquecento; it only changes the photographs.
So book with slack around anything fixed like a wedding or a cruise, and cancel a full day before the start the moment a plan wobbles.
10/10!! Taxi trouble, but our guides were accommodating and the friendliest ever. They helped my fiancée pull off a day-of surprise proposal, perfect and so special. Nino and Christina, we'll remember you forever!
A vintage Tuscany drive earns its reputation on quiet Chianti roads, where the car's slowness belongs to the landscape around it.
Book about 50 days ahead for peak months, confirm the nominated driver can manage a manual gearbox, and pick a private-driver tour if the wine tasting will outrun the driving. Every tour here refunds in full when you cancel a day ahead.
Straight answers about routes, driving, wine stops and booking a vintage Fiat 500 tour in Tuscany.
Florence2026Self-driving takes more attention, but you feel every mile of the country roads and notice the vineyards and villages as you pass. A guided route, usually in convoy with a lead car, handles the navigation so you can focus on the car itself.
On self-drive tours, no. The nominated driver must be a regular manual driver, because the vintage car needs an experienced touch. Automatic-only drivers should pick one of the guided rides with a private driver instead.
A category B driving licence is enough for these classic cars, and drivers on the tours must present a valid licence. Non-EU citizens also need an International Driving Permit, carried together with the national licence.
Drivers must be at least 18, which is also the legal minimum driving age in Italy. One sunset wine tour additionally asks that drivers do not weigh more than 130 kg.
Book about 50 days ahead to secure a spot in the busiest travel months. For harvest season, when popular wineries fill quickly, plan two to four weeks ahead at minimum.
Some self-drive tours include a wine tasting, so keep it to one glass and hand over the keys if you plan to drink more. Other Chianti tours bring a private driver precisely so guests can taste freely.
These cars are all manual, with no power steering, so steering at low speeds takes real effort, and the gearbox asks for more attention than a modern one. Starting on an uphill slope can be a challenge too.
No. The five-hour countryside tour includes a Tuscan ham and cheese tasting with a glass of Chianti, while the shorter two-hour winery ride pairs tastings with a private driver. Some options carry no food or wine at all.
Wear comfortable clothes and shoes, since stops can involve some walking. In summer add sunglasses and sunscreen; bring a light extra layer for windy stretches at altitude in spring or autumn.
Chianti combines rolling hills, vineyards, olive groves, cypress trees and stone farmhouses, with winding roads that dip into small wooded valleys. Around San Gimignano and Volterra, the hilly towns make the manual transmission more of a factor on the slopes.
Tours there pair the drive with a picnic at a pecorino cheese farm, and the landscape draws people on its own: the hills and fields were shaped over centuries into the Renaissance rural scene you still see today.
The sunset wine tour runs rain or shine, and the electric Florence tour helps you reschedule if heavy rain arrives, with free cancellation up to 24 hours before. Light rain rarely stops the drive, though an open-top car calls for a jacket.
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Five hours behind the wheel of a restored Fiat 500 through the Tuscan hills, with fuel, insurance and a ham and cheese stop included, and free cancellation up to 24 hours before.
