722Drive a vintage Fiat 500 through the Chianti hills, then taste the wines where they grow. Follow a guide along quiet Tuscan roads to a family-run winery, with a light lunch or sunset tasting waiting at the end. Pick your route and book your car today.
A Chianti day in a vintage Fiat 500 comes in two basic forms: you take the wheel yourself, or a driver handles the narrow country roads while you ride. Some outings add a winery visit, a tasting or lunch, others keep the day about the drive. The one difference that decides it is who drives, and that usually follows from whether you want wine with lunch.
Bring your driving licence on the day, and if nobody in your group drives a manual car, pick one of the chauffeured Chianti tours instead, where a professional driver handles the car for you.
Two hours with a private driver, a winery stop and tastings, the quickest way to pair the car with wine
A multi-course Tuscan lunch at a family-run farm in Chianti Classico, with wine and olive oil pairings
Seven hours from Certaldo, the deepest Chianti route, with wine, olive oil and lunch all included
The only one where you take the wheel, with a driving lesson first and two hours in the Chianti hills
The day starts in the Tuscan hills, on quiet secondary roads that wind between vineyards and olive groves. A vintage Fiat 500 carries you through the countryside at a relaxed pace, with your guide close behind in convoy and photo stops at viewpoints along the way.
After roughly ninety minutes of driving, you pull in at a family-run winery. A guided tasting of Chianti wines and local olive oils comes with cheese and Tuscan specialties, plus a light lunch of regional dishes. Then it is back behind the wheel for the return through the same wine country.
A short safety briefing happens before you set off. You drive yourself, so the nominated driver needs to be comfortable with a manual gearbox.
Green marks the lowest price. Prices per person.
Highly recommend escaping the city for this.
Bella was energetic and even showed us the olive mill early. Loved driving the vintage cars after adjusting, top down, great views and stops, tasty lunch, brought wine home. Know manual!
10/10! Taxi trouble, but our guides were beyond accommodating and so friendly. They helped my fiancée pull off a day-of surprise proposal perfectly. Thank you Nino & Christina, forever grateful!
Gabriel was an excellent guide, knowledgeable and fun, clearly proud of his country. Lunch was honestly just ok, but the views and wine made up for it.
Fun drive once I got used to the car and roads.
We'd dreamed of Tuscany, planned a Vespa tour, but the Fiat 500 won out. Driving those charming cars on winding roads was a delight, guides friendly and knowledgeable. Easy 5 stars.
It was wonderful. Amazing views, unreal little car. Been to Florence many times but never saw these spots. Daniele was brilliant, so passionate about history, vineyards, the Galileo museum. And that olive oil! Delighted!
Most reviewers praise their guide by name and call the drive through the hills the highlight of their trip.
Rain and even a taxi strike could not spoil the day, and one guide helped stage a surprise proposal.
Several wished the day lasted longer, after the tasting and the drive ended sooner than they expected.
Start from the format: a 2-hour ride with a private driver, a 4-hour Chianti Classico winery and lunch day, or a 7-hour full Chianti outing from Certaldo. Choose the date, then check the option list for that day before you commit.
Compare what each option adds: some bring a Tuscan appetizer or charcuterie board with the tasting, others a full multi-course lunch. Check who drives, because several Chianti tours put a professional driver in the car for you.
Confirm the date, the option and the number of guests, then pay through the marketplace. Every Chianti tour here allows cancellation up to 24 hours in advance for a full refund, and the confirmation arrives by email.
If you drive, bring your driving licence and, where the option requires it, a credit card in your name. Non-EU drivers need an International Driving Permit alongside their national licence. Read the confirmation message for anything else the operator asks for.
Arrive a few minutes early at the meeting point in central Florence, or be ready where the pickup applies. Wear comfortable shoes for getting in and out of the low car, and listen to the briefing on the vintage gearbox before you set off.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
You choose the format. Two tours hand you the wheel of a vintage Fiat 500 and follow a guide in convoy. The others put a professional driver in the car, so you ride as a passenger and taste freely.
The vintage cars all have manual gears. On the self-drive tours the nominated driver must be a regular manual driver; automatic drivers cannot take the wheel. A briefing on handling the car comes before you set off.
The chauffeured tours carry a maximum of two guests per car plus the driver, and the full-day one needs at least two participants. The self-drive countryside tour fits up to three adults, or two adults and two children aged 3 to 12.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Most tours start from a meeting point in central Florence. One full-day option meets its driver in Certaldo, in the middle of Chianti itself, so check the departure town before you plan the morning.
Bring a valid driving licence for any self-drive option; the minimum driver age is 18. The sunset wine tour also asks for a credit card. On the chauffeured tours you sign a short car rental agreement so the insurance covers you.
The Chianti hills pair two pleasures, a slow country drive and a glass of Chianti at the vineyard that grew it. Which tour gives you the right mix, when to book it, and what to pack: all settled here.
Set aside about four hours for the tour and leave a cushion before any train or dinner reservation, since starts can shift.
Book about 50 days ahead in the busiest months, and two to four weeks ahead during the harvest, when the wineries fill first.
On the self-drive options you need a full licence, real comfort with a manual gearbox, and one glass of wine at most after a tasting.
The road drops away in a long curve between vineyards, and the little car at the front of the line is doing about the speed a bicycle tourist would choose. That is the point.
A vintage Fiat 500 suits these winding Chianti roads because its small size makes it easy to place on narrow lanes, and its slow pace turns the drive itself into part of the experience, the way between stops included.
The format matters as much as the car. On the main Chianti tour, a professional driver takes the wheel and each car carries two guests, so you sit back and watch the olive groves go by.
Drivers in Italy must be at least 18 and hold a valid licence, and on the chauffeured tours that rule belongs to the driver.
Small groups move through these country lanes better than any bus ever could. A convoy of two or three little cars can slip through a hill village, park where a coach cannot, and stop for a viewpoint without blocking anything.
Worth it, then, if you want the drive and the wine in one slow morning, with every stop earning its place.
The day starts in central Florence, where the driver and the little cars wait. Out through the old walls, up into the hills, and the city noise drops off within half an hour. The convoy sticks to quiet secondary roads at a relaxed pace, with vineyards and cypress lines replacing traffic.
A family-run winery is the midday anchor. There you walk the grounds, hear how Chianti wine and olive oil are made, and sit down to a guided tasting.
Food almost always comes with it: some tastings bring cheese, salami, cured ham and bruschetta, and several tours add a traditional Tuscan lunch, sometimes a full multi-course one at the farm itself. The best things to buy after a tasting, regulars say, are the bottles you want shipped home.
Set aside about four hours for the whole thing, start to finish.
Arrive a few minutes early
The guide leads the whole way
Food is usually served with it
Included on the longer tours
Leave a cushion before any fixed plan
That four-hour shape is why the timing matters: a start can shift a little, so leave a cushion before a train, a dinner reservation or anything else with a clock on it. The tour runs in all weathers, and the routes follow quiet back roads with the guide in convoy the whole way.
Two dates on the calendar decide whether you get the day you want. The first is the general busy season, when the cars are booked out well in advance. Travelers who plan Tuscany trips in the peak months book about 50 days ahead to be sure of a spot.
The second is the harvest. Late summer and early autumn pull everyone toward the same handful of family-run wineries, and they fill first. For a food or wine outing in Florence and Chianti, two to four weeks ahead is the working window, and during the harvest the popular wineries can be fully committed inside weeks.
Chianti vintage Fiat 500 tours sell out well ahead of the date Book about 50 days ahead for peak months, and during the harvest plan two to four weeks out
A morning slot is the one worth chasing in high season. You get quieter country roads and winery rooms that are not yet crowded. If your dates fall in the harvest, book the tour first and fit the rest of the trip around it.
Three formats, three different afternoons. The two-hour tour pairs a scenic ride to San Miniato al Monte with a family-run winery stop, a Tuscan appetizer of local products, and a wine and olive-oil tasting, all with a private driver. It fits a short stay in Florence that still wants a winery visit.
The fuller day is Florence: Vintage Fiat 500 Tour with Chianti Winery & Lunch. A private driver takes you into the Chianti Classico countryside, stops for a panoramic view over Florence that locals favor, then settles you at a family-run farm for a multi-course Tuscan lunch with Chianti wines and extra-virgin olive oil.
Four hours, and the closest thing to a whole wine-country day in the car.
| 2-hour winery tasting drive | 4-hour private-driver Chianti Classico tour | Self-guided Chianti Classico drive | |
|---|---|---|---|
| Duration | 2 hours | 4 hours | About 4 hours |
| Who drives | Private driver | Private driver | You, in convoy or on your own |
| Food and drink | Tuscan appetizer, wine and olive-oil tasting | Multi-course Tuscan lunch, wine and olive oil tastings | Tastings are only suggested stops, easy to skip |
| Who it suits | Short stays that want one winery stop | The fullest wine-country day | Drivers who want the roads most of all |
Not every reader drinks. On the self-guided Chianti Classico drive, wine and olive-oil tastings are only suggested stops and nothing more, so someone focused on the countryside can simply skip them. Departures for the guided tours run from Florence, which is where the day begins either way.
Half the appeal is the wheel itself, so this is the choice worth a slow think. Taking it is legal from 18 with a valid licence, and non-EU drivers also carry an International Driving Permit alongside their national one.
A classic B licence covers these vintage cars. EU licences need nothing extra, and UK photocard holders are fine without a permit too.
The bigger test is the gearbox. Every vintage 500 out here is manual, with no power steering and a gearbox that can ask more attention than a modern car's. Some original models have an unsynchronized box that may need double-clutching.
The Chianti self-drive option requires a nominated driver who already knows a manual car, and automatic-only drivers cannot take the wheel. It is not a driving lesson, though a briefing on handling the vintage car comes before you set off.
Riding with a driver costs you nothing but control. From Florence: Self-Drive Fiat 500 Tour in Chianti is the compromise: two hours behind the wheel in the Chianti wine region, with a lesson first and the countryside roads doing what they do best.
On the guided tours, quiet back roads and a guide in convoy take the navigation off your hands.
The question comes up at every tasting table: can the nominated driver still sip? Italian law sets the general blood alcohol limit at 0.5 g/L for most drivers, and zero for anyone in their first three years behind the wheel and for professional drivers.
Stay above 0.5 and up to 0.8 and it is an administrative violation; past 0.8 it becomes a criminal matter, and penalties can reach a driving ban, licence revocation or even a year in prison.
On most of these Chianti tours the law never becomes your problem. The guests are not allowed to drive at all: a professional driver takes the wheel, and you drink as much of the Chianti as the tasting offers. That is the quiet advantage of the chauffeured format.
For the self-drive days, the arithmetic is simple. One glass is the ceiling, and the sensible move is the one regulars make: taste, then hand over, or save the glass for the terrace after the engine is off.
The tour is a wine trip, not a lesson in road law, and the narrow Chianti lanes reward a sober hand anyway.
Plans in Tuscany move around, and the booking terms here allow for that. The Florence-based tours let you cancel up to 24 hours in advance for a full refund, so a shifted itinerary or a forecast that turned grey does not trap the booking.
That deadline is the one to write down; inside 24 hours, the refund is gone.
| If this happens | What happens then |
|---|---|
| Cancel at least 24 hours in advance | Full refund on the Florence tours |
| Weather or a vehicle problem means the operator cannot run the day | The change goes through your marketplace booking |
| Traffic, weather or road closures on the day | The itinerary may shift, and the operator adjusts the route |
The itineraries themselves are flexible by design. Routes can vary with traffic, weather or road closures, and a start time can slide a little, which is why the cushion before any fixed appointment matters.
Weather rarely kills a day here. The drives run in light rain and in all conditions, and severe weather leads to rescheduling with a new date. If the forecast is unsettled, book early enough that rescheduling still has room on your dates.
Florence is the departure point, and that simplifies the morning. The chauffeured tours meet in the city centre, the self-drive tours pick up the cars at a garage near the historic core, and the countryside begins within half an hour of the walls.
That works whether Florence is your base or a stop. City-based travelers walk to the meeting point; anyone city-hopping can slot the tour into a morning and still be back for a late lunch. The four-hour format leaves the afternoon free for the Uffizi or the train to Siena.
One practical note: no hotel pickup comes with these tours, so plan to reach the meeting point on foot or by tram. Leave the car behind.
Parking near the historic centre eats time the tour is meant to spend in the hills, and the little Fiats are the only vehicles you want on these roads anyway.
The little car decides the wardrobe. Doors are narrow, seats are low, and photo stops mean climbing in and out several times a day, so closed-toe shoes and comfortable casual clothes are the foundation. Leave the bulky bags and anything that fights for space in the cabin at the hotel.
Between stops you spend real time outdoors: vineyard terraces, viewpoints over the hills, long lunches on farm tables. That is where a hat, sunscreen and a light layer earn their space, especially in the afternoon sun of summer.
The camera does more work than you expect. A guide helps with poses and angles at the scenic stops, so nobody needs to arrive knowing how to pose. Expect pictures beside the car as well as from it, and the vintage bodywork makes a better backdrop than most city walls, regulars joke.
Pack light, wear the right shoes, and the car asks nothing else of you.
The tour day ends back in Florence, but the roads it uses belong to places worth a return trip on your own. Greve in Chianti is first.
Piazza Matteotti has a distinctive funnel shape, Greve's historic market square, and its arched porticoes shelter shops and workshops selling local food and crafts. A statue of Giovanni da Verrazzano stands in the middle, and the porticoes make it a good free stop with room to sit.
Castellina in Chianti keeps a stranger curiosity. Via delle Volte is a covered walkway through the historic centre, protected by ancient walls and built as an underground defensive route that could withstand gunpowder explosions. It was originally open to the sky and gradually roofed over by the houses pressed against it.
Badia a Passignano rounds out the day among vineyards. The abbey shows visitors a large cloister, a kitchen and a refectory with Ghirlandaio's Last Supper fresco, and the church holds frescoes by Alessandro Allori in the Chapel of San Giovanni Gualberto, where the saint's tomb lies.
Any of the three pairs well with a return drive, and they keep the wine country alive after the tour car is handed back.
It was wonderful. Amazing views, unreal little car. Been to Florence many times but never saw these spots. Daniele was brilliant, so passionate about history, vineyards, the Galileo museum. And that olive oil! Delighted!
A vintage Fiat 500 day in Chianti earns its slot in a Tuscan itinerary. Pick the chauffeured format if you want the wine and the lunch without the wheel, and the self-drive if the narrow roads are the draw.
Book about 50 days out in peak season, two to four weeks during the harvest, and the day is yours.
Straight answers about routes, tastings, driving rules and timing before you pick your Chianti Fiat 500 experience.
Florence2026The Florence wine tasting and lunch tour lets you drive a vintage Fiat 500 through the Tuscan countryside after a short briefing, with your guide leading in convoy. The sunset wine tasting tour from Scandicci is another self-drive option, and it pairs the drive with a Chianti wine tasting and a charcuterie board.
No. Three of the tours include a private driver: the Chianti winery and lunch tour, the short two-hour winery tour, and the seven-hour Chianti tour that starts in Certaldo. You ride as a passenger and spend the drive enjoying the vineyards and olive groves.
It varies by tour. One includes a winery visit with a Tuscan appetizer of local cold cuts and a wine and olive oil tasting. The two longer ones add a traditional Tuscan lunch paired with Chianti wines, plus an olive oil tasting served with bread.
The four-hour self-guided, self-driven Chianti Classico tour treats wine and olive oil tastings as suggested stops you can skip, so the countryside drive becomes the whole point. You set your own pace through the region.
You need a valid driving licence and to be at least 18, and every Chianti driving tour requires you to be comfortable with a manual gearbox. Non-EU citizens also need an International Driving Permit carried alongside their licence. UK photocard holders do not need an IDP.
It has no power steering, so low-speed turns take more muscle, and some models have an unsynchronized gearbox that needs double-clutching. The car feels smaller and lighter than anything modern, and the roads are quiet secondary streets at a relaxed pace. A briefing before you set off covers the rest.
Florence is the practical choice if you are staying in the city: several tours meet there, including the self-drive countryside, winery and lunch options. The longest tour, a seven-hour day with tastings and lunch, starts in Certaldo in the heart of Chianti.
Between two and seven hours. The shortest is a two-hour drive with a winery tasting, the self-drive lunch tour runs three hours, and the full Chianti day with a winery visit, tastings and lunch takes seven.
Give yourself a cushion of about four hours around the tour itself. The start time can shift, and country roads mean the return does not land exactly on the minute. A late-morning tour pairs well with an evening plan rather than an afternoon train.
Italy's limit is 0.5 g/L for most drivers, and zero for drivers under 21 and those with less than three years' experience.
On the Chianti tour with a full tasting and lunch, guests are not allowed to drive at all, so the question only arises on the self-drive options. If you are driving after a tasting, limit yourself to one glass.
On the self-drive countryside tour, each car takes up to three adults, or two adults with two children aged 3 to 12 riding free. The guided seven-hour Chianti tour is not suitable for very young children, and its cars hold a maximum of two guests plus the driver.
For a food or wine outing in Florence and Chianti, plan two to four weeks ahead, and book earlier during the harvest when popular wineries fill quickly. All the tours on this page allow free cancellation up to 24 hours in advance, so an early booking carries little risk.
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Take the wheel in Chianti, taste local wines with a light Tuscan lunch, and cancel up to 24 hours ahead for a full refund.
