myTour in Italy · Siena area
You get behind the wheel of a 1960s Fiat 500 and follow a guide in convoy to Monteriggioni and a winery near Castellina in Chianti for lunch. Pick it for the car, the noise and the photos, not for comfort or a serious tasting.
First, the question everyone asks: who drives? You do. The inclusions list says "Vintage Fiat 500 with professional driver", but the itinerary says you get behind the wheel and follow the guide caravan style, and almost every review describes guests driving after a test lap. One guest in 2017 was driven by the guide all day. If you can't drive a manual car, ask the operator before you book rather than assume.
The cars are the real thing: toggle ignition, crash gearbox, no air conditioning. Reviewers also report no working turn signals, loose seat belts, a smell of fuel and the odd breakdown, and a 2019 guest's car had to be abandoned in a storm. Others call that half the fun. Know which group you're in. The route goes to Monteriggioni's walls, through the hills to Castellina in Chianti, and to the Poggio Amorelli winery near Castellina, a Chianti Classico estate, for lunch with two wines and olive oil on bread.
Lunch is the other split. The listing promises bruschetta, pasta and cantucci with Vin Santo; several reviewers since 2023 got a shared platter of cold cuts and a rice salad instead. The meeting point is Via Genova 29 in Certaldo at 9:30, while older reviews describe a depot at Badesse near Siena and a paid transfer (one couple paid EUR 100 from central Siena). A 4.3 rating from 52 reviews tells you the rest: loved by car people, a risk for everyone else. The Vespa tour has newer machines and a far steadier record.
Via Genova 29, Certaldo. Confirm the meeting point after booking: past groups started near Siena.
A practice run in the yard to get used to the gearbox and the brakes.
Park outside the walls and walk the tiny medieval village.
Scenic roads and photo stops on the way into Chianti Classico.
Tuscan starters, a main and dessert with two Chianti wines and olive oil on bread.
The convoy returns to the start.
★★★★★Before driving out of the lot, you get to do a quick and safe test drive to get comfortable with driving these things, something I really appreciated [...] These are not pristine cars; they are rentals and as such they take quite a beating.
★★★★★To make this experience authentic the wind in your hair instead of the air conditioning, the toggle ignition and the gearbox of the time. [...] we visited the Poggio Amorelli winery, one of the best wineries in the area, where we tasted excellent quality wines accompanied by a lunch based on typical Tuscan products!
★★★★★Brush up on your manual driving skills and you'll be good to go. If you have driven a volkswagen beetle, pretty much the italian version. Beautiful country side. Great tour guide. Great host at the winery.
Read next:
You drive. The listing mentions a professional driver in its inclusions, but the itinerary and nearly all reviews describe guests at the wheel in convoy behind the guide. Ask the operator in writing if you need to be driven.
Yes. The Fiat 500s are 1960s cars with an old manual gearbox and toggle ignition. Even experienced drivers say it takes a few minutes; there's a test drive before you set off.
The listing gives Via Genova 29 in Certaldo at 9:30. Earlier reviews describe a depot near Siena. Check your confirmation and arrange transport early, since pickup costs extra.
The itinerary names Poggio Amorelli, a family estate near Castellina in Chianti, inside the Chianti Classico zone. Lunch comes with two Chianti tastings and olive oil.
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A vintage Fiat 500 through the Tuscan hills to a farm lunch and two Chianti tastings.
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