Iconic

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Tuscany

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Iconic ~ Tuscany ~

Chianti Countryside

The quintessential Tuscan experience: Rolling hills, hilltop villages, and postcard-perfect views as far as the eye can see. This is the Tuscany you’ve imagined.

If you’re looking for the iconic Tuscan road trip that you’ve seen in the movies, you’ll want to be based in the Chianti region for a serene countryside stay. Your day trip opportunities will range from wineries, to farms, to hilltop villages, to major cultural hubs like Florence and Siena, and beyond!

At a glance…

  • 5-7 nights

    Give yourself time! You will easily be able to fill a week up with day trips alone, but you’ll also want to allow yourself some time to enjoy your countryside stay & soak up il dolce far niente.

    1. Fly into Florence airport OR arrive at Florence train station from another leg of your trip

    2. Rent your car

    3. Drive to Chianti (approx 1 hr)

    Note: I recommend renting your car from the airport to avoid the busy streets around Florence

  • Recommended:

    • Car rental ✔

    • Scooter rental ✔

    • Taxis ✖

    • Public Transit ✖

    • late summer/early fall

    • spring/early summer

  • Premium. The Chianti region is arguably the most iconic in all of Tuscany, so you can expect a few more crowds and a bit of a higher price tag to match.

What to do?

Taste the world-famous chianti wines at one of the many local vineyards

Take a drive along the scenic Chianti wine road

Sample the wares that the many nearby farms have to offer

Explore the many nearby hilltop medieval towns & villages

Indulge in a slow day simply enjoying your agriturismo

  • Visit a medieval castle or estate; many have onsite restaurants & wine tastings

  • Discover the bustling cultural hubs like Florence & Siena

What’s on the menu?

Some local specialties:

Piano Piano Tips

  • Since this is a countryside escape, I highly recommend taking advantage of the many vineyard agriturismo options in the area, since a car is highly recommended to explore all that this area of Tuscany has to offer.

    An agriturismo is a working farm stay, typically family run. There is no better way to experience the slow, authentic Tuscan lifestyle while enjoying fresh farm-to-table meals.

    Other, more luxurious options include historic estates/castles, or luxury countryside hotels.

    If you have a larger group, you might opt to rent an entire countryside villa.

  • Look no further for the ultimate romantic destination! Whether it’s for a honeymoon, an anniversary trip, or just because, there is quite possibly no place more romantic on earth - especially for lovers of wine & history!

  • Tuscany is ideal for a child-friendly Italian experience! You will have plenty of space for your kiddos to run and play at your countryside stay, a car to travel at your own pace & pack all necessities for day trips, and the opportunity to experience a working farm! What could be better?

  • A car is highly recommended to explore everything that this area has to offer. This is a countryside escape, after all, and no public transit will be available to some of the most iconic places that should not be missed.

    I recommend renting your car at the Florence airport, where the surrounding roads are much easier to drive than roads within the city. Even if you are staying in Florence for a few days, it is worth getting a cab to the airport to pick up your car.