500 Vintage Tour - Chianti wine tour - Small group
Traveler rating
5.0/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is 500 Vintage Tour - Chianti wine tour - Small group worth booking?
500 Vintage Tour - Chianti wine tour - Small group is a 7-hour experience in San Gimignano, Italy, from $125 per person. It scores 67 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 67 / 100
- Rating
- 5/5 (6)
- Duration
- 7 hours
- From
- $125 per person
Enjoy a memorable 7-hour journey through the Tuscan countryside aboard a charming vintage Fiat 500. Relax as a professional driver guides you along the scenic roads of the Chianti region, passing rolling hills, vineyards
What you get
About this experience
Enjoy a memorable 7-hour journey through the Tuscan countryside aboard a charming vintage Fiat 500. Relax as a professional driver guides you along the scenic roads of the Chianti region, passing rolling hills, vineyards, and iconic cypress-lined avenues. Discover picturesque medieval villages, where you can wander through historic streets and take in breathtaking panoramic views. During the tour, visit a traditional wine cellar and savor a tasting of renowned Chianti wines, paired with a delicious Tuscan appetizer and lunch. You’ll also sample locally produced extra-virgin olive oil served with fresh bread, offering an authentic taste of the region. This small-group experience is designed for comfort and ease, allowing you to fully immerse yourself in the beauty, flavors, and timeless atmosphere of Tuscany without any stress.
What's included
Included
- Tuscan appetizer + lunch and 2 Chianti wine tasting
- All fuel and operational costs
- Extra-virgin olive oil tasting with bread
- Vintage Fiat 500 with professional driver
- Small group tour guide
Not included
- Gratuities
- Pick up and drop off at accomodation
What you'll see and do
Tuscany
Be enchanted by the medieval villages on the rolling hills of the famous wine region and much more.
Pass by without stopping
Where it starts and ends
Meeting point
San Gimignano
Via Genova 29, Certaldo, 50052 FI.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Via Genova 29, Certaldo, 50052 FI.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 6 travelers per booking
- Operated by
- myTour in Italy
Know before you go
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- The tour take places rain or shine. 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 due to the size of the vehicle, a maximum of 2 people are allowed in a car.
- Please do not wear flip-flops but shoes
Photos
What travelers are saying
Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.
The guide
2 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
1 mentionReviewers describe the commentary as informative rather than scripted.
Organization
1 mentionPickup, timing, and logistics are described as running smoothly.
Good for families
1 mentionReviewers traveling with kids report it landed well with their group.
Traveler reviews
6 verified traveler reviews for 500 Vintage Tour - Chianti wine tour - Small group. Ratings and reviews provided by Viator and Tripadvisor.
The most fun day
My family of 5 had the most amazing experience with Fauzi and Sofia while touring San Gimignana. We rode in vintage Fiats to our first stop, the town of San Gimignano. We had the best gelato at Gelateria Dondoli and wandered through the town for about an hour. We then headed to Altezza Vineyard for yet another amazing experience. We ended our day at Tenuta Torciano Vineyard. Fauzi and Sofia got us safely to all our stops and gave us wonderful tidbits of information along the way. A truly unforgettable experience! ❤️
Response from the operator: Dear Customer, Thank you for your feedback! We are delighted to hear that you and your family had an unforgettable experience with Fauzi and Sofia. We will gladly share your kind words with them. Thank you again for choosing us, and we hope to welcome you again soon. Best regards, my Tour in Italy
via Tripadvisor
Passion between past present and future
The 500 tour is definitely a fantastic experience. Marco prepared us for the experience with a very interesting historical excursus. He is Fauzi then accompanied us to visit San Gimignano. Invaluable were Marco's advice on what to see and what to taste. Then they accompanied us to visit two wineries where we tasted excellent wines typical of the area. We highly recommend this experience, we found competence, professionalism and friendliness. The tour in 500 took us back in time but at the same time we found a well-structured and organized reality. Good guys.
Response from the operator: Dear Customer, Thank you for your feedback! We’re glad you enjoyed the 500 tour, San Gimignano, and the winery visits with Marco and Fabrizio We truly appreciate your recommendation and hope to welcome you again soon. Best regards, my Tour in Italy
via Tripadvisor (translated)
I can't believe we drove a Vintage Fiat in Tuscany!
Late late review BUT what an amazing experience that was. My husband and I visited Tuscany last August and booked a tour that included a vintage Fiat to be driven through the Tuscan Hills. We had an amazing tour guide whom chaparoned us while driving a Vespa. It was quite the experience of a lifetime never to be forgotten! Highly recommend it!
Response from the operator: Dear Customer, We’re delighted that you and your husband enjoyed the vintage Fiat tour and the Vespa ride through the beautiful Tuscan hills.It sounds like a truly unforgettable adventure.We appreciate your recommendation and hope to welcome you again for another amazing tour soon. Best regards, My Tour In Italy.
via Viator
Fun day in the Chianti countryside
What a fun day this was! The tour company was "My Tour". Riding in the vintage Fiat 500 with my husband and 9 year old son, along with Duccho, our spirited, English speaking driver, was the best way for us to see the Chianti region. Driving through the windy roads while following the rest of our group on vespas and e-bikes was quite an adventure. We stopped in a quaint little village- Castellina in Chianti, then on to a wine tasting and lunch at Poggio Amorelli vineyard, which was lovely, as we sat with the rest of our group and shared our vacation stories. We were scheduled to visit a 2nd village, but there were heavy thunderstorms, so the whole group headed over to Gelateria Castellina, where I had the most unbelievable Stracciatella gelato! A point of note- When booking this tour, if you want a driver to be provided, be sure to select tour # TG19. There was some confusion about our initial booking, as they thought we wanted to drive the vehicle ourselves. Everything worked out in the end. Also, the description of the tour says its from San Gimignano. We were picked up from our SG hotel in a van and taken to the departure point 30 minutes away. This was unexpected, and the only reason I mention it is because the van driver was speeding almost the while time. I was very uneasy during that journey. I highly recommend this tour. A great way to see the area if you aren't renting your own vehicle.
via Tripadvisor
Absolutely loved this tour! Such a...
<p>Absolutely loved this tour! Such a unique way of seeing the Tuscany countryside. The areas/ villages we visited and passed through were so beautiful and gave us a great overall feel for the area. Lunch was also fantastic and felt like a real Italian experience. Highly recommend this fun and unique tour!</p>
via Viator
Good to know
- Duration
- 7 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $125 to $150
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Who runs this experience
Operated by myTour in Italy, who run 51 experiences we rank across 5 cities, with an average Outty Ranking of 57.8.
See everything myTour in Italy runsWhy this scores 67
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
500 Vintage Tour - Chianti wine tour - Small group: questions travelers ask
Practical detail on this experience, plus the wider planning questions for San Gimignano.
How much does 500 Vintage Tour - Chianti wine tour - Small group cost?
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Prices start at $125 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in San Gimignano usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does 500 Vintage Tour - Chianti wine tour - Small group take?
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Plan for about 7 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in San Gimignano is not rushed.
Is 500 Vintage Tour - Chianti wine tour - Small group worth it?
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It holds an Outty Ranking of 67 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in San Gimignano, and how flexible the cancellation terms are.
Can I cancel or reschedule 500 Vintage Tour - Chianti wine tour - Small group?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is 500 Vintage Tour - Chianti wine tour - Small group suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 7-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book 500 Vintage Tour - Chianti wine tour - Small group?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in San Gimignano can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in San Gimignano and add a light layer if any part of the 7-hour experience runs outdoors or after sunset.
Where does 500 Vintage Tour - Chianti wine tour - Small group start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central San Gimignano within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in San Gimignano?
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On Outty we rank every San Gimignano experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Wine and food tasting in an organic family winery, Tuscan Cooking Class, Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit San Gimignano?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in San Gimignano?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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