30 Photos That Will Make You Want To Take A Road Trip Through Tuscany

Whenever we visit a new destination, we often find ourselves saying “This is my new favorite place in the world!” Well, the Chianti Region of Tuscany was no different. Whether it has to do with the picturesque medieval villages, the rolling green countryside – or if it’s just the Chianti Classico wine talking – the region certainly knows how to charm.


Tuscany is widespread and not easily accessible via public transportation, so we definitely recommend renting a car and making daily road trips a part of your itinerary. Our car was from Economy Bookings and was perfect for exploring without limitation. We stumbled upon heaps of small Tuscan villages devoid of any tourists, as absolutely picture-perfect as could be. A car also makes it much easier to tote around all the wine you’re bound to pick up while doing all those Chianti tastings! But don’t take our word for it. Have a look at these photos that are bound to have you dreaming up your next road trip under the Tuscan sun in no time:

30 Photos That Will Make You Want To Take A Road Trip Through Tuscany

30 Photos That Will Make You Want To Take A Road Trip Through Tuscany


Driving Around Tuscany

Driving through the Tuscan Countryside in Chianti

Tuscany Vineyards


Plump grapes almost ripe for vinification

Tuscany Italy

Tuscany Italy

Vineyard in Chianti Region Tuscany

Vineyard in Tuscany Italy

So much wine!

Vineyard in Tuscany

Chianti Classico Winery

The classic Black Rooster symbolizes the prestigious Chianti Classico variety of wine is made here.

Roadtrip in Tuscany

Colle di Val d'Elsa Tuscany

The quiet medieval town of Colle di Val d’Elsa

Road Trip In Tuscany

O Outside Voltarre Tuscany

Scenic Drive Through Tusany

The scenic highways are just begging to be explored

Paleo Parade Siena Tuscany

The residents of Siena prepare for the Paleo, a highly competitive horse race

Siena Tuscany

Paleo Horse Race Siena Tuscany

Paleo Siena Tuscany

Fans cheer on their neighborhood riders during the Paleo

castel san gimignano Tuscany

Countryside of Tuscany

Small Model of castel san gimignano Tuscany

castel san gimignano Tuscany

San Gimignano, also known as the Manhattan of Italy


Gelataria Dondoli castel san gimignano

Multiple Gelato World Champion and owner of Gelateria Dondoli

Gelato In Tuscany

You can’t go to Tuscany and not have gelato…. every single day.

castel san gimignano

Hillside town in Tuscany

Sunset over Poggibonsi

We recommend staying in the central town of Poggibinsi. While not a particularly charming town, it is the perfect place to base your road trip. There are plenty of charming villas to choose from and we opted for a beautiful Airbnb rental with views of San Gimingando out our window! Our host Alessandra was absolutely wonderful and gave us fantastic recommendations on what to see and do in the area. She was the one who recommend L’officina della Cucina Popolare in nearby Colle di Val d’Elsa for us and we suggest you have at least one of your dinning experiences her. We ate a lot in Italy and this was hands down our favorite meal. Be sure to make your reservation early as sometimes you need to book days in advance.


Have you ever visited Tuscany? Did you find it as charming as we did?


A huge thank you to Economy Bookings for making our amazing Tuscany road trip possible!

Meet: Dan Moore

Dan is the photographer, social media strategist and second half of the A Cruising Couple team. He has been living and traveling full-time in various countries since 2011. His award winning photography has been featured on National Geographic, CNN and New York Times Travel.


  1. Great photos! I wanted to lick the cone of gelato! We so enjoyed those when we visited Italy!

  2. Wow, just wow! I am so upset that I missed Tuscany, these photos make me even more upset. (enough to drown my troubles in Italian wine)
    rebecca recently posted…The real myth of the Giants CausewayMy Profile

  3. Wow! that looks amazing you guys, I really want to go to Italy and Tuscany in particular. Love the looks of the car, what kind was it? I think having a vehicle is the only way to go 🙂
    Dariece recently posted…Sunset Sunday: September 27thMy Profile

    • Yes, I totally agree! You can experience so much more when you have the freedom to simply stop at will. I hope you get to go back to Italy, and def Tuscany! 😀 Unfortunately, I don’t remember which car that was… that’s Dan’s stuff. 😉 But, we didn’t have much of a problem scoring a nice one, so hopefully, it will be the same for you. 😀
      A Cruising Couple recently posted…5 Reasons to Visit Paris in the SpringMy Profile

  4. Nice stuff! It makes me want to book a car today and head off! I love being able to just cruse around and stop where and want. I guess you could say the freedom of exploring the country instead seeing it from a bus window!
    David recently posted…5 Adventures You Must Have in Lisbon- PortugalMy Profile

    • Couldn’t agree more, David! Freedom to stop and explore at will is what will make your vacation extra special. Road trips are one of the best ways to see a country. 🙂
      A Cruising Couple recently posted…5 Reasons to Visit Paris in the SpringMy Profile



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