road trip in Tuscany tips

Are road trips one of the most complete and immersive travel experiences possible or not? I think yes and I’m here writing this article so that you can discover one of the most exciting road trips in Italy: a road trip in Tuscany, along Chianti’s Road (and not only!).

A road trip in Tuscany is a once in a lifetime experience.

Although Italy offers a wide range of road trip itineraries, the route I will talk about is one of the most beautiful pathways you can explore in this amazing country.

This itinerary could end up easily amongst the “5 best road trips of the world” but let’s keep it real and set off to explore this incredible region and its beauties.

How do you plan a road trip in Tuscany?

It’s time to plan your holiday in Tuscany.

How many days do you need in Tuscany?

In my opinion this itinerary requires 14 days or more.

If you want to enjoy the incredible landscapes, the delicious regional tastes and, of course, the wines, two weeks are the perfect amount of days.

Let’s leave the rush to our working days and start to enjoy Italian way of life!

What is the best month to visit Tuscany?

Visiting Tuscany is always a good idea!

This motto applies independently of the weather.

This region gives its best of itself in each season.

Colors, tastes and traditions are the main actors here for the whole 12 months.

In autumn Tuscany is glorified by the foliage.

In winter you could soak up the vibrants cultural atmosphere in the major cities of the region, such as Florence, Siena or Lucca.

During spring discovering regional traditions and tastes is much easier thanks to dozens of food festivals and fairs, organized all over the region. 

My advice is traveling between late September and October or between April and May, when temperatures are comfortable and there are fewer crowds at the major sights.

As expected, summer ushers in high temperatures and heavy crowds.

Where do you begin your Tuscany Road Trip?

Florence is the biggest city in the region and its airport is well connected with the most important European airports.

This city is a must-see but it is so filled with wonders that will require more than a weekend.

This city is amazing and it deserves to be discovered quietly, slowly and gently.

Now that we have set up the key points of your road trip in Tuscany it’s time to start the itinerary.

#1 The Chiantigiana towards Siena

From Florence you take the Regional Road 222, known as Chiantigiana, which connects the Tuscan capital with Siena.

This road is one of the most scenographic and beautiful routes in Italy.

It winds through gentle hills, picturesque villages and is lined by lush vineyards.

Besides the natural wonders, the Chiantigiana is a renowned food and wine route: here Chianti is the king!

If you are traveling along the Chiantigiana you should definitely make the time (and room in your stomach) for a stop in a typical osteria or trattoria, where you could taste an excellent glass of Chianti, produced by the restaurant’s owner himself.

Take your time to discover this amazing corner of Tuscany. 

The best way to do that in my opinion, is taking part in a wine degustation “in the field”, choosing one of the most ancien wineries in the Chianti’s area.

This is by far one of the most complete experiences you could do here.

But there is more!

If you are a true wine-lover, you cannot miss the Wine Museum in Greve, a small village nestled in the vineyards.

I think this is the best way to fall in love with this region.

#2 Monteriggioni

Once you are close to Siena you might consider making a detour toward Monteriggioni, one of the most stunning medieval walled cities in Europe.

This village is worth a visit!

You can explore the ancient city center in a few hours.

Walking along the top of the castle walls is an experience I recommend you do.

From the battlements, on the top of the wall, you could catch a glimpse of the surrounding countryside and feel on your skin the fresh summer breeze.

#3 San Gimignano

Another medieval village you cannot miss in Tuscany: San Gimignano.

This is the perfect town where you can rest and recharge your batteries.

The historical centre is made up of dozens of cobbled alleys and narrow streets where you can find any kind of restaurant, from the modern bistrò to the old taverns, including wineries. 

This little medieval village offers a wide range of places to eat and picking one it’s an hard choice.

The best decision, in my opinion, is taking part in a wine tasting with lunch included. 

In this way you could try regional culinary specialties such as cheeses, cold cuts and crostini accompanied by excellent Vernaccia di San Gimignano, one of the best wines in Tuscany.

After lunch you can start exploring the town and its charming squares among others Piazza delle Erbe, Piazza del Duomo and Piazza della Cisterna where you will find the most important historical building of the village.

And where you can get a good ice cream as well.

If you decide to spend two or more days here I advise you to get this useful museums-pass that will allow you to visit without problems the Civic Museums of San Gimigliano.


#4 Lucca

Next stop on your road trip in Tuscany is Lucca and the perfect way to explore this town, in my opinion, is by bike.

This splendid Renaissance City offers you a precious opportunity to park your car and burn a few calories.

You spent almost a week driving, after all!

Renting a bike for one day (or less) costs nothing: price range from 10€ (3 hours) to 15€ (one day).

So you don’t have any excuses!

Once you rented your bike you could ride along the Renaissance city wall, a 5 km tour around the old town, and enjoy the relaxing vibes that came from the alleys and the piazze.

Otherwise you could explore the surrounding countryside and try to spot the Apuan Alps in the distance.

You have so many options to make this stop unforgettable.

#5 Elba Island – the perfect ending for your road trip in Tuscany

Lucca was your last mainland stop of this itinerary in Tuscany.

Now head towards Piombino, a coastal town where you can catch a ferry for Elba Island, the gem of the Tuscan archipelago. 

Elba is a goldmine of experiences. 

Enjoy the amazing beaches that you can find all over the island, explore the inland little town such as Capolveri or the fascinating Villa San Martino, once Napoleon’s summer residence.

You have so many options here!

And guess what, a car is the best way to get around the island!

As I said at the beginning of the article, summer is the worst season to visit the island which is stormed by tourists.

In my opinion spring is the best time to visit it, when the temperatures are fresher and the weather is steady.

Spring is definitely the best time to organize excursions here.

Not to mention the several wine tasting experiences proposed by the local wineries

Undoubtedly one of the most romantic and beautiful locations where to taste wine is Tenuta delle Ripalte, a resort framed by a breathtaking landscape, where you can catch the real essence of this calm and quiet piece of Tuscany.

Here is the highlight of your road trip in Tuscany:

I advise you to drive on Provincial Road 25, between Marciana Marina and Marina di Campo, at sunset and when the air is clear and there are no clouds.

You could spot an overseas Corsican’s silhouette. 

The icing on the cake that will make your road trip memorable.