Tuscany is very well portrayed in movies, and once you arrive you’ll feel like you’re in one. If you explore Tuscany by car, which is definitely the way to go, you’ll find yourself on long winding roads encountering peculiar signs that look like this.

Tuscan Road Signs

Ok, they’re actually pretty accurate signs, but paired with the backdrop of romantic landscapes, quaint hilltop towns, and the nostalgic old world feeling you get basically everywhere in Italy, these signs have a way of making navigating Tuscany feel like a storybook adventure- some sort of Italian Alice in Wonderland. It could not be any better.

But unlike Alice, you will probably want to gather some information beforehand about responsible matters like car rentals, road laws, gas mileage, or train schedules before visiting Tuscany. I recommend this great PDF written by a guy who sounds like he might be somebody’s dad.

Travel Tips from Dick Calabro

I say this because if my dad knew all about Tuscany this is the sort of excellent practical advice he’d probably give me. The PDF even recommends working out before you come to Italy. I suggest this as well.

Prior to your trip I recommend no less than 3 days a week of vinyasa yoga followed by a chakra meditation session, and two days of semi long distance running- just to pre-burn the calories you will consume in wine.

Also before you go to Tuscany, read up on popular Tuscan Towns to visit and pick a few that sound fun. Pair the towns with a few vineyards and use the tips in my next blog post <link> where I give you far from expert advice on how to go wine tasting and where to stay in Tuscany.

Here are a few top tuscan towns to get you started- I didn’t add Florence because obviously you’re already planning to go there.

Top Tuscan Towns

Siena
Siena was the rival of Florence back in the day and is now the 2nd largest town in Tuscany. Although very historical, it’s a bit large and official for my tastes. It would probably most fun during the Palio di Siena.

San Gimignano
Loved this place! When I was researching Tuscany this was my top pick to visit. Those buildings.. that skyline!
Watch my video of Tuscany and San Gimignano

Volterra
From the photos I’ve seen, Volterra looks like it’s one of the most visually interesting towns in Tuscany. I didn’t get to visit Volterra, but of course I wanted to.

Mainly because of Twilight- I’m not gonna lie.

It just looked amazing in the movie.. aside from the part where the unsuspecting tourists were led into the chambers of the Volturi for a feeding.

Even with the existence of an ancient royal coven of vampires, if I could go back and pick a third Tuscan town to visit, it would be Volterra.

Lucca
The town of Lucca features a bike/ walking path around the outside walls and what’s said to be a more impressive duomo cathedral than the even the one in Florence!

Pisa
It’s leaning towner time! Pisa would be great to visit (and take a #selfie with the tower) but it is closer to the coast and a bit of a hike from the heart of the chianti wine region.

Montepulciano
This is supposed to be one of the prettiest medieval hilltop towns with the most impressive main square. They have their very own wine called Vino Nobile so be prepared to do a little tasting of it while in town and be sure to have a driver if you do more than taste.

Montalcino
This one is close to Montepulciano, it’s known for its great wine, and it has a castle at the edge of the town where you can do a tasting. Make it happen.

Here is a more complete list of Towns in Tuscany

Be sure not to miss the final video of my Tuscany Trilogy: Tour of Chianti Wine Region and Siena