Vintage Fiat 500 Tour: Chianti Wine & Lunch from San Gimignano

Drive the Chianti hills in a classic Fiat 500, tasting wine where it's made

A 7-hour scenic tour of Chianti and San Gimignano in a vintage Fiat 500 with a professional private driver, including two wine tastings at San Quirico winery, a Tuscan lunch, and olive oil tasting with bread. The small group travels the most scenic roads around the region with a live guide in English, Spanish or Italian, and all fuel and operational costs are covered.

Step-by-step itinerary

Chianti tour with wine tastings

• Visit San Gimignano
• Visit San Quirico winery

The experience

The Fiat 500 itself is the point: a restored classic that moves through Chianti's narrow roads and switchbacks the way they were built to be driven. Your professional driver handles the curves and the navigation while you sit back and watch the landscape shift from vineyard to hilltop village. The car holds a small group, so it's not a coach full of strangers. It's intimate enough that the guide can talk without shouting over an engine.

The route takes you through San Gimignano first, the medieval town with its famous towers rising above the valley. From there you head to San Quirico winery, still in San Gimignano, where you taste two Chianti wines in the setting where they're made. Before the tastings, you sit down to a Tuscan lunch, not a rushed plate, but a proper meal. The olive oil tasting with bread comes as part of the same stop, so you're tasting the region's staples in one place, not jumping between venues.

Seven hours means you're not racing. The pace lets the landscape sink in and gives the guide time to explain what you're seeing instead of just pointing. All fuel costs are built in, so there's no surprise at the end, and if you're staying in San Gimignano or anywhere in Chianti without a rental car, this solves the day. You don't arrange transport, you don't navigate, you don't hunt for a parking spot at the winery.

What’s included

• Vintage Fiat 500 with professional driver.
• two Chianti wine tastings at San Quirico winery.
• Tuscan lunch.
• olive oil tasting with bread.
• small group tour guide in English, Spanish or Italian.
• all fuel and operational costs.

Before you book

Days and timesEvery dayDeparts at 09:30Last departure this season: 15 Nov

Book up toStart time

AgesAdult (18 and older) · Child (15 to 17 years) · Under 15: can't be booked

GroupUp to 4

Live guideEnglish, Spanish and Italian

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated today

Good to know

Low physical effortPublic transport nearby

Operated by myTour in Italy

Is this one for you?Book this tour if you're staying in San Gimignano or Chianti without a car: the private driver and fixed route mean you skip the rental desk, the GPS and the hunt for parking at the winery, and you arrive at each stop ready to taste instead of stressed about where to leave the keys.

Traveler reviews

4.35★★★★★★★★★★

52 verified traveler reviews

5 ★36

4 ★7

3 ★3

2 ★3

1 ★3

Read all the reviews ›

Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Italian.

Can children come?

Yes. Ticket types: Child (15 to 17 years). Children under 15 can't be included in the booking.

What exactly happens at San Quirico winery?

San Quirico winery is where you taste two Chianti wines and enjoy your Tuscan lunch. The olive oil tasting with bread is also part of the stop, so you're experiencing the region's key products in one place.

Do I need to arrange my own transportation to the tour start?

The tour operates from San Gimignano. If you're staying in the area, public transportation options are available nearby to reach the meeting point, or you can arrange your own transport to the start location.

Is the tour suitable if I'm not very fit?

The tour is suitable for all physical fitness levels. You spend most of the day seated in the vintage Fiat 500, and the winery stop involves walking at a comfortable pace.

What's included in the price?

The tour includes all fuel and operational costs, the vintage Fiat 500 with professional driver, two Chianti wine tastings at San Quirico, a Tuscan lunch, olive oil tasting with bread, and a small group guide.