The Ultimate Tuscany Road Trip

Picture this: 👀

You’re driving along a gravel road; 🛣

It extends as far as the eye can see before being elegantly swallowed by the horizon. ☀️

You look ahead before shifting your focus to the rearview mirror; “wow”, you think to yourself. 🤩

Not a single car in sight. 🚙

Luscious yellow-tinted green hills featuring cypress trees roll outwards in all directions. 🌳

Vineyards run along the road, protruding into your peripherals. 🍷

Small masonry villages decorate the hilltops. 🏘

🇮🇹 Welcome to Tuscany, Italy. 🇮🇹

If you’re someone who enjoys spontaneity, saving money, and following an itinerary that allows you to absorb all that a country has to offer:

Then an Italian road trip is for you!

Buuuuut, why Tuscany specifically?

Well, it’s home to two of Italy’s grand medieval cities and features the wine treasures of Chianti.

Oh -

It also presents one of the most picturesque, breathtaking, and extraordinary scenic landscapes this planet has to offer.

And the best part of all?

We’ve done the research for you!

Welcome to:

The Ultimate Tuscany Road Trip Itinerary


Image showcasing the production fields of the wine in tuscany

Start: Florence (where you’ll hire/drop off your rental car)

End: Arezzo

Length of trip: Literally as long as you want it to take (we recommend no less than five days)

Trip Destinations: 1. Florence > 2. Lucca > 3. Pisa > 4. San Gimignano > 5. Siena > 6. Val d’Orcia > 7. Montepulciano > 8. Arezzo


Image mapping out the italy road trip


This road trip has been structured to loop back to Florence eventually; it is primarily designed to incorporate the whole Tuscany experience.

Think rolling hills, golden light, delicious wine, picturesque villages, and some of the best food you’ve ever eaten in your life!

Soooo, what do you even bring while driving in Tuscany?

Here are a few of our underrated essentials:

A Photographic Device 📷
You want to make sure you have something to look back on and trust us, you will be taking a ton of photos. Also, make sure you bring backup batteries and portable chargers!

A Travel Sim Card 📱
Seriously, we’re not just saying that because we sell travel Sim Cards. You don’t want to get lost while on the road, or even worse, break down! Coming prepared with one of our travel sims ensures you can access maps at all times and allows you to call for help if needed. Click Here to view our entire collection.

Sunglasses 😎
It gets pretty sunny along the hilly ranges of Tuscany; although this is more of a quality of life improvement, we highly highly recommend it as it’ll save you squinting along the drive and potentially missing out on some beautiful landscapes!

Annnddddd, that’s a wrap. 🌯

We kept it short to fit as much as we could without overloading you with information, but don't be fooled…

This is the road trip of a lifetime! 😎

We'd love to hear if you guys have ever experienced road-trippin' overseas.

Maybe you have some underrated road trip tips? 🤔

Let us know by dropping a comment at the bottom. 🤓

Happy and safe travels, everyone! 🧡 ­ ­

🌍 Heading Overseas Soon? ✈️ ­ ­

Save yourself the time of looking for a prepaid SIM by getting a travel SIM from us before you fly! Click below to check out our entire collection.

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