Highlights:

• Explore the Chianti countryside in an original Vintage Fiat 500 with your own local driver
• Travel along panoramic backroads through vineyards, olive groves and Tuscan villages
• Visit two family-run Chianti wineries and taste wines and extra-virgin olive oil where they are produced
• Enjoy a traditional Tuscan lunch with wine on the first day
• Spend the night at a countryside agriturismo with swimming pool and wake up surrounded by the Tuscan hills

Slow down and experience Chianti in a Vintage Fiat 500

If you want to experience Tuscany beyond a classic day trip, give yourself an extra day and leave Florence behind aboard one of Italy’s most iconic cars.

With your private local driver taking care of the road, this 2-day journey allows you to simply sit back and enjoy Chianti. You’ll travel along small panoramic roads through vineyards, olive groves and villages, stopping at family-run wineries to discover the wines, food and people of the region.

And when most day-trippers start heading back to Florence, you’ll stay. Spend the afternoon and night at a countryside agriturismo, relax by the pool and enjoy the slower rhythm of rural Tuscany before continuing your Fiat 500 journey the following morning.

Day 1 — From Florence to the Chianti Countryside

Your journey begins at our office in Florence’s Oltrarno district, where you’ll meet your local driver and your Vintage Fiat 500.

Leaving Florence behind, you’ll climb into the hills overlooking the city and follow quiet countryside roads towards Impruneta and San Casciano, passing olive groves, vineyards, historic villas and small Tuscan villages along the way.

Around lunchtime, you’ll stop at a family-run Chianti winery for a guided visit and tasting, followed by a traditional Tuscan lunch paired with local wines.

And since your driver is taking care of the Fiat 500, you are free to enjoy the wine without worrying about the drive afterwards.

In the afternoon, continue deeper into the countryside before arriving at your Tuscan agriturismo, usually around 3:30 pm.

The rest of the day is yours. Relax by the pool, enjoy the peaceful surroundings and experience an evening in the Tuscan countryside at your own pace.

Day 2 — More Chianti and back to Florence

After breakfast at the agriturismo, enjoy a slow morning in the countryside before your driver and Vintage Fiat 500 pick you up again at approximately 10:00 am.

Rather than simply taking the quickest road back to Florence, you’ll continue exploring along scenic country roads, passing through the area around Impruneta and enjoying another glimpse of everyday Tuscan life.

Before returning to the city, stop at a second family-run Chianti Classico winery for a visit and tasting of three wines and extra-virgin olive oil, accompanied by traditional Tuscan cold cuts.

Then it’s time for one last drive in your little Fiat 500, following panoramic backroads towards Florence.

You’ll arrive back at our office at approximately 12:30 pm, where you can collect any main luggage you left with us before departure.

What’s Included

• Vintage Fiat 500 with private local driver
• Scenic drives through Florence’s hills and the Chianti countryside
• Visit to a family-run winery on day 1
• Traditional Tuscan lunch and wine tasting
• One-night stay at a selected countryside agriturismo
• Swimming pool access, season permitting
• Breakfast on day 2
• Pickup from the agriturismo by Vintage Fiat 500
• Second family-run Chianti winery visit
• Tasting of 3 wines and extra-virgin olive oil
• Traditional Tuscan cold cuts during the second tasting
• Return to Florence

Dinner is not included and can be enjoyed directly at the agriturismo, allowing you to choose freely from the menu according to your preferences.

What to Bring

• Small backpack or overnight bag
• Comfortable clothing and shoes
• Sunglasses and sunscreen during the summer
• Personal essentials for your overnight stay
• Valid ID

Before You Go

• Guests do not drive the Fiat 500. Each car comes with a private local driver.
• Vintage Fiat 500s have limited luggage space, so please travel with only a small overnight bag.
• Your main luggage can be safely left at our Florence office and collected when you return.
• Small vintage-style overnight suitcases can be provided upon request.
• Main luggage transfer to the agriturismo can be arranged as an optional extra.
• Maximum 2 guests per Fiat 500. For larger groups, several Fiat 500s can travel together.
• The accommodation is usually Agriturismo Inalbi or a similar selected countryside property, depending on availability.
• Routes, wineries and accommodation may occasionally change according to availability and local conditions.