Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

Badge of ExcellenceSiena, Italy
Self Drive Vintage Fiat 500 Tour from Siena Tuscan Hills and Winery Lunch

From $162.47

Select Date and Travelers

up to 24 hours before the experience starts (local time)

  • 7 hours 30 minutes
  • Pickup offered
  • Mobile ticket
  • Offered in: English


See Tuscany in classic Italian style by exploring the rustic region via a vintage Fiat 500, the classic, beloved and diminutive Italian automobile. Get picked up at your hotel in Siena and then ride to the stunning hilltop town of Monteriggioni, cruising through the rolling hills of Chianti along the way. Stop at a local vineyard and sample some delicious Italian wines with a hearty lunch of local fare. Follow the guide in a caravan. The number of participants on this small-group tour is limited to just ten, so you’re sure to get plenty of personalized attention from the guide.
  • Drive a vintage Fiat 500 through Tuscany
  • Cruise from Monteriggioni through the breathtaking Chianti hills in a classic Italian car
  • Dine on Italian cuisine during a 3-course lunch at a local winery
  • Learn about the area from your host, who’ll lead the caravan of cars
  • Hotel pickup and drop-off from Siena included
  • Small-group tour limited to 10 people ensures a more personalized experience

Sample Menu






Cantuccini with Vin Santo

What's Included

  • Vintage Fiat 500 car to drive during tour
  • Tour escort/host
  • Winery tour
  • Lunch
  • Tasting of different wines, water
  • Gratuities
  • Pick up and drop off at accomodation

Meeting and Pickup

You can head directly to the meeting point, or request pickup

Meeting point

  • Via della Resistenza, 95, 53035 Badesse SI, Italy

    If you have not selected the pick up and drop-off option, please meet our staff member in Badesse.

Pickup point

  • Via Giuseppe Garibaldi, 72, 53100 Siena SI, Italy

    In front of Hotel Minerva

End point

This activity ends back at the meeting point.

Pickup details

If you select the option with pick up service included, please note that the pick up point is in front of Hotel Minerva, in Via Giuseppe Garibaldi 72, 53100, SI.

What To Expect

Step outside your hotel and then step inside your Fiat 500 for the day. This unique guided tour allows you to see Tuscany via a vintage Fiat 500, a beloved diminutive car. With two aduls per car and only five cars, this small-group tour ensures plenty of attention from the guide. 

After getting behind the wheel and following your guide caravan style, head to Monteriggioni, an impressive walled medieval village. Explore the diminutive town, taking in its ramparts from the Middle Ages and popping into small shops. Get back in the car and keep driving, cruising through the classic rolling hills of Tuscany, taking in the grape vine-clad landscape and the hills that are crowned by rustic villas. 

Pull up to Poggio Amorelli, a local winery, and indulge in a hearty Tuscany three-course lunch, complete with a wine tasting, of course. Later, start the Fiat 500 again and step on the pedal to meander back to Monteriggioni again. After a brief stop, ride back to Siena to conclude your day of Italian automotive style. 

Sample Menu

• Crostino with paté di olive
• Crostino with fresh tomatoes
• Bruschetta with extra virgin olive oilMain Course
• Pasta con pomodoro
• Cold cuts of prosciutto, salami, cheese and crostino with truffle olive oil Dessert and Wine
• Cantucci (biscotti cookie) with Vin Santo dessert wine

Castellina in Chianti (Pass By)

Cantinetta di Monteriggioni (Pass By)

Castello di Radda

30 minutesAdmission Ticket Free

Chianti Road (Pass By)

Casale dello Sparviero Winetour

2 hours Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Minimum age to drive is 18 years. A valid driver's license is required in order to attend the tour.
  • A valid credit card is required as a guarantee if you sign up as a driver.
  • Stroller accessible
  • Previous experience using manual gears is required. Your guide reserves the right, at his or her discretion, to terminate the participation of any driver who is unable to control the car safely without any refund.
  • Please note that due to the size of the vehicle, a maximum of 3 people are allowed in a car.
  • Near public transportation
  • Infants must sit on laps
  • At the time of the rental a pre-authorization on credit card will be made as a guarantee for any damage, which will be canceled upon return from the tour if there has been no material damage to the vehicle.
  • Infant seats available
  • Most travelers can participate
  • The tour will take place also with rain. In case the weather does not allow us to attend the tour due to heavy rain or wind, clients will be offered an alternative or a full refund. In case a storm occur during the tour and the guide decide that for security reasons is better not to continue with the tour you will be escorted back to the departure place but if this happen no refund will be issued as this is beyond our control.
  • Please note that pick up and departure are not included in the price, a pick up service can be requested at an additional cost.
  • Please do not wear flip-flops but shoes
  • This tour/activity will have a maximum of 12 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.

Traveler Photos

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Featured review
Amazing way to travel through the landscape of the Chianti region in Tuscany and the car was fun to drive. Our guide, Paolo, was very friendly and informative. Definitely recommend this trivandrum a great way to spend my birthday


49 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 49 reviews
Must do!!!!
Derek, Oct 2023
Of course, 1960s Fiat makes for an interesting challenge…and yes you can smell gas, but we LOVED this experience! The guide and other guests were so much fun. We bonded over laughs and poking fun at some lackluster driving moments, but this made for an experience we’ll never forget! The scenery, towns and wineries were outstanding. If we had a free day, we’d come back for the Vespa tour!
Response from Host, Oct 2023
Dear Customer, Thank you for sharing your feedback. Our customers are our priority, and we are happy to know that you enjoyed everything about this tour. Thank you for choosing us to travel through Italy. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
Pretty Dry "Tour"
Daniel_H, Oct 2023
To be fair, the description says you will be accompanied by an "escort", not a guide. However, our escort said as little as he could possibly get away with. We didn't know what town we were in unless we specifically asked him. He even seemed reluctant to guide us with hand gestures in and out of parking situations. So you have a working a car, and some stops in some cool towns, but nothing like every other "tour" I've booked in various places around the world, during which you are made to feel really welcome and usually have some quality interactions with the guide. It is what it is, but I don't think it deserves a high rating, just on this basis. As long as you know what you are getting, fine. If it were only that, I would give it another star, but we paid for the pickup/drop-off, over 100 Euros for two 20 minute rides, and they simply abandoned us at their warehouse (at least in our perception--I really can't say if anything was happening in the background). Things happen, I know, but when we got back to the warehouse with our cars and scooters, the leader/representative (or whatever he was) never said a word to us--turned his back and started toward his personal car. I chased him down and asked about my return ride and he said just wait here 5-10 minutes (in about 4 words). Then he left. It seemed kind of obvious to me that no one knew we were there waiting (all other guests seemed to have their own transportation and were gone) and after a half hour we were getting pretty anxious--we were alone at a warehouse in a little dingy office with really not much of an idea of where we were or how to find a taxi. I had trouble getting the tour operator's phone number to work--I think there is a typo at one location in the operator info--but finally got in touch with them and the lady got someone there in about 10 minutes to take us back. So it worked out in the end after waiting 45 minutes or so. I disputed the transfer charge with Viator (at Viator's suggestion) and was denied, the operator saying that it was a traffic issue, out of their control. Again, things happen, but the fact that we were just left there with really no idea what was going on, along with the nearly total lack of communication even during the tour, adds up to something I wouldn't do again. Re the cars, they are what you would expect. A little oil smell, a grabby clutch, no turn signals, no seat belts, etc. All part of the fun and it always started. However, even if you have driven manual transmissions, this one takes a little time to get used to. I wouldn't want to learn on it, but I enjoyed it. Also, realize that the pickup/drop-off is not to your hotel, but to a location in Siena that was about a 20 minute walk for us. The Fiat ride itself starts and ends in Badesse, a town near Siena.
Vintage Fiat tour- a one of a kind experience. It’s not for everyone.
Lynne_B, Sep 2023
The countryside was absolutely gorgeous, we enjoyed the hill towns, winery tour and the light lunch. We’ll love telling stories about the drive in the vintage Fiat, but frankly we were worried it would break down so many times. Fortunately, my friend who drove the car was familiar with this model- otherwise, it would have been a disaster. The others in our group were on Vespas, and I think they enjoyed the comic relief we provided in the Fiat. I wish our tour leader would have joined us and engaged at the stops we made. It was such a unique experience/ very hard to give an overall rating. In the end, we were really happy we did it.
Response from Host, Sep 2023
Dear Customer, Thank you for taking your time and sharing your feedback with us. We are glad to know that you had a beautiful experience and enjoyed the tour itself. As you've said too, Fiat is a Vintage vehicle and for this reason it may have seemed a little bit scary for you and like the car was going to break down. You didn't have to worry at all, as the vehicles are controlled before the tour starts to be sure that our customers will drive safe. There is no danger to drive the Fiat or Vespa either. The tour leader has been always at the disposal of each customer and was taking care of everyone, sorry for the moments that you've felt like wasn't engaging you enough at each stop. Overall, we are happy that you experienced a unique tour with us and hope we will have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
Worst ever
Bobby_S, Sep 2023
Please do yourself a favour and stay away. We booked a day, arrived (after taking 25min taxi) to warehouse in car park, waiting 1.30hr with other people to be told it is cancelled and then had to get taxi back
Response from Host, Sep 2023
Dear Customer, Thank you for the feedback and sharing your experience with us. We are really sorry for the inconvience and for what happened. As we also explained it to you on the phone too, we had a last issue with our tour guide and that's why we unfortunately had to cancel the tour. Our guide was not feeling well and notified us for this at the last moment. The only solution was to cancel the tour and reschedule it for another time or give our customers a full refund, which was the thing we did to you in this case. Again we are sorry and we request your understanding, as what happened was something unpredictable for us and our guide too. We are really sorry. For any further concerns you may have please contact us at our email address Thank you for your understanding. Best regards, My Tour in Italy.
Carefree exploring in Chianti!
Marek_W, Sep 2023
Brilliant way to experience the Chianti Wine Region. Easy and carefree, Unique memories made with other travellers. Special day and great Tour guide
Response from Host, Sep 2023
Dear Customer, Thank you for sharing your feedback with us. Glad to know that you had a good experience with our staff and other travellers too. Thank you for appreciating our guide's work and hope to have you again in our upcoming tours in the near future. Best regards, My Tour in Italy team.
Amazing experience driving a fiat 500 in Tuscany, Siena
Jeanine_W, Sep 2023
Giorgio and Francesco were the perfect guides for an incredible experience. Loved driving the the cutest little cars. Loved the locations and the Scenery. Loved the wine tasting of Tuscany Wines. In all it was one of my favorite days in Italy.
Response from Host, Sep 2023
Dear Customer, Thank you for taking your time and sharing your feedback with us. Glad to know that you had an incredible experience with our guides. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
Fiat 500 fun
Jan_C, Sep 2023
We had the best time ever! Matilda was so knowledgeable and great fun. Francis was amazing and giving me the confidence i needed. I hadnt driven a manuel for many years, but it all came back to me. The winery was lovely. Francis and Matilda even drove my daughter and i home as it was on his way. So very kind. I would highly recommend this tour!!!
Response from Host, Sep 2023
Hello from My Tour, Thank you for sharing your feedback with us. We are glad to know that you had a good time on the tour. Many thanks for the good words for our guides, we are happy that you appreciate their work. Thank you for recommending the tour to other customers too. Hope to have you again in our upcoming tours in the near future, to give you more experiences like this one. Best regards, My Tour in Italy team.
Fun and Exciting but have a good breakfast
Berangely_C, Jul 2023
At first didn’t know what to expect! I was worried we would be super hot in these vintage Fiat cars because of the no air conditioning but surprisingly with sunroof and open windows it was fresh breeze in July! Loved all the spots and the wine on the tour was fantastic! The only negative was that there really isn’t a lunch. We were traveling with 3 kids between 10-12 years old and they were starving. It’s more of a tasting with charcuterie boards and appetizers. Nothing that a child would really like. We still made the best of it but they shouldn’t advertise “lunch”. It’s more appetizers with wine. Regardless, tour guide was great and it was a real fun experience
Response from Host, Jul 2023
Dear Customer, Thank you for your positive feedback. We are really glad to know that you liked the tour and had a good experience. As for the lunch, the customers are well informed that this tour has included A LIGHT LUNCH. We are really sorry for the confusion. Regardless, we are happy to know that you had a fun experience. Hope to have you again in our tours in the future. Best regards, My Tour in Italy team.
Super fun Fiat 500 tour
Astrid_M, Jul 2023
Loved driving the little Fiat 500, of course it’s an old classic car which doesn’t drive as smooth as a normal car but that’s part of the experience and charm. We loved every single bit of it! The only improvement we can think of, is either to change the description of the lunch or to actually serve what’s described in the add. We did not have a three course lunch. It was just a charcuterie with a bit of rice salad. Luckily we weren’t that hungry. Apart from that it was an amazing day!
Response from Host, Jul 2023
Dear Customer, Thank you for sharing your experience with us. We are happy to hear that you have enjoyed this tour. Hope to see you again in our other upcoming tour, in order so we can show you the improvement we have made and give you another great experience with us and our staff in Italy. Bset regards, My Tour in Italy team.
The Fiats are an Accident Waiting to Happen
Meghan_C, Jun 2023
My wish with this review is not to cause problems for the company but to provide other potential travelers a realistic view of this tour. Four of us went on the tour, 2 drivers and 2 passengers. Although the drivers have had much experience with manual and even with vintage manual vehicles, the fiats were in the worst condition that they had ever driven! Signals and break lights were not working, seat belts weren’t functional, multiple times the gas pedal was stuck to the floor, the breaks were sketchy and one vehicle needed to be pushed to start (you can see in the photo two of the travelers pushing the car that the guide was trying to start). In short, these vehicles just aren’t safe to be on the road with other cars and pedestrians. Before beginning we received zero instruction or what to expect. We were very unimpressed with our guide who was not at all engaging. Miraculously, we made it between the different stops, first being a stop for gelato (which we paid for out of pocket), then we arrived to a small town to browse the shops. Then finally we made it to the winery, which was enjoyable. We were given several wines to taste, however, contrary to what is advertised a lunch of bruschetta and pasta along with dessert, we received a platter of cold cuts and cheese to share with the other guests and a cold rice salad— which barely passed as a snack. All in all, the surroundings were beautiful and if you are considering going with this company, we all suggest that you rent the Vespas or e-bikes instead and hope you get a friendlier guide.
Response from Host, Jun 2023
Dear customer, Thank you for sharing your feedback with us. The idea of this tour is to experience nostalgy while driving this vintage vehicles. As you know this vehicles are oldmade so they cannot be as modern as the new cars today. The vintages are in good condition although they are old. We have more than 20 years in a row organizing this tour and our customers never had any problem while driving them. The vehicles are always checked before being used for driving and we ensure you that they are safe to ride. We always see the safety of our clients as our first priority, so there is not any reason being concerned for this part. In the second place, we always choose the best wineries for our customers to enjoy their time there. We are sorry for the innconvience and the experience you had while our tour. Please if you want contact us at our email address to explain us with more detail the full experience you had on the tour and the dissatisfactions you have. Best regards, My Tour in Italy team.
Was ok
Luci_F, Jun 2023
Diego drove our fiat and was great ! But by the time we got to winery we got only 2 sips of wine and some cheese and meats that would have never filled anyone ! Winery was a waste of time
Response from Host, Jun 2023
Dear Luci, Thank you for sharing your experience with us. We're glad to hear that you enjoyed our Vintage Fiat 500 Tour! We always do our best to offer travellers the best experiences in Tuscany. As for the small amount of wine provided in the winery, we're sorry that this could not meet your expectations, but since it was a tasting, the quantity couldn't be more than what had been offered. We hope to see you again also in the future and to accompany you in other interesting Italian experiences. Best regards, myTour in Italy
Fiat 500 tour
wanda_o, Jun 2023
Even when we had a good time. The Fiat 500 we arranged for the tour many of them were out of service. They give us a Polaris when we asked if there had another type of car in order to us not to loose the tour. (The Fiat need maintenance. )
Fiat 500’s. Awesome
Gary_M, Apr 2023
Was able to spend the wonderful day with my son, on his birthday, and his family. My wife and I were trying to find a surprise that he would never figure out. It worked.
Exciting and fun way to vist Chianti
AnnaMarie_M, Apr 2023
Amazing way to travel through the landscape of the Chianti region in Tuscany and the car was fun to drive. Our guide, Paolo, was very friendly and informative. Definitely recommend this trivandrum a great way to spend my birthday
Love that Fiat. It was star of show everywhere we stopped!
Clark_Z, Sep 2022
All! The Fiat and Vespas and two guides. All friendly and created a great time. GREAT JOB!! Route was scenic and explanation of where we were and wine tasting and food were very well thought out.
True Adventure
Janice_S, Jun 2022
The scenery and luncheon/wine tour, and all the stops were great! Driving these windy roads is exciting and takes skill. The guide Diego was absolutely the best- considering these cars are Vintage by age only- it took a special person to deal with all the mechanical issues with grace and patience! He was kind, beyond helpful, and fun and went out of his way to make sure everyone was happy! If you like adventure and you don’t need perfection of a Collector’s car, do this! It’s a trip to remember.
Tour fantastic - pickup/drop off information incorrect
Suzette_Y, May 2022
The tour was fantastic. Fabio, the tour guide, was fabulous! Everyone had a fabulous time. HOWEVER, - The information on Viator is not accurate! Under “what’s included”, they state “hotel pickup and drop off on request”. However, we had to pay $100 euros from central Siena (5 mike drive) for pick up/drop off. Didn’t get the cost until too late to cancel.
Response from Host, May 2022
Dear Suzette, thank you for your feedback. We're glad that you enjoyed this experience with our team! We're sorry for the misunderstanding, on Viator has the "pick-up and drop-off" on request, it means that we can provide pick-up with an extra charge if customers can't reach the meeting point on their own. I put here the Viator's note about pick-up "Please note that pick up and departure are not included in the price, a pick up service can be requested at an additional cost." I am sorry but we try to be the most clear as possibile to avoid misunderstandings. Anyway, we hope you like the experience and we hope to see you again on another tour all around Italy!
A perfect, fun way to see Tuscany!!
Ellen_C, Apr 2022
This tour is fantastic!! I booked it on my husband's birthday and it couldn't have been more memorable. Yes, the car is old and it was temperamental, but thats the fun. My husband is 6'4", so it was interesting to see him behind the wheel, but he did it. The guides were so nice and knowledgeable and made sure we stopped in all the right sports for perfect pictures. The winery tour was nice and the food was plentiful. Couldn't have asked for a better birthday experience!
Response from Host, Apr 2022
Dear Ellen, thank you for your feedback. We appreciate it so much. We're glad to hear that you spent such a lovely time with our staff in one of the best scenery of Tuscany! Hope to see you again for another experience with us!
Tuscany fairytale
Nina_G, Sep 2020
Alex was a pro. The best guide ever. He explained everything. It wouldn’t be the same without him. The winery owner Andrea showed us nothing but hospitality and kindness. Good food and excellent wine. Worth every euro. Thanks guys.
Vintage Fiat 500m Tour - Fantastic
DARRYL_V, Oct 2019
This was such a cool tour in a Vintage 500 that you drove for the whole tour. The hosts were attentive and outstanding with stops for a wine tour and munch, medieval village, ice cream and pictures at the most photogenic winery. Book this tour to see Tuscany as the locals experience it.

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