Your Ultimate Tuscany Road Trip, Planned: Best Itinerary Ideas & Practical Tips

Your Ultimate Tuscany Road Trip, Planned: Best Itinerary Ideas & Practical Tips

Sun in your face, wind in your hair and the iconic Tuscan countryside all around you: what could be better than a Tuscany road trip? A trip through Italy’s most famous region is a bucket list item for many and for good reason.

I have been to Tuscany several times (I even lived there for awhile) and I keep going back. Even though it may seem overrated, it really is one of the most beautiful places in Italy and, arguably, the world.

So, if you are getting ready to head off on your own Tuscany road trip, look no further than this practical and inspirational guide with helpful travel tips and, most importantly, the top spots that belong on your itinerary.

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First things first – how long should a Tuscany road trip be?

Can we just make it forever? Of course, one of the first questions to have a clear answer on is how long you have available to road trip Tuscany.

Maybe it is just one stop on a larger Italy itinerary or it’s the prime focus of your adventure. Honestly, you could make a road trip in Tuscany your whole vacation, there is that much to see.

Ideally, I suggest a Tuscany road trip of 7 to 10 days. This way, you are able to spend at least one night in each of the most beautiful places in Tuscany.

However, you can definitely adapt the itinerary suggestion I have laid out from my experience to fit your needs.

The length of your trip may also depend on what areas you are more interested in seeing

If you are figuring out this road trip on your own and want some personalized help, I got you! If you would like me to create a custom itinerary for you, check out my trip planning services. Or if you just have a question or two, ask me in the comments.

Tuscany Road Trip Itinerary

This itinerary outline highlights the top destinations I recommend you visit and in what order for the most efficient drive.

If your timing allows it, I highly recommend staying even more than 1 night in several of these destinations where I believe there is more to discover! I will highlight what I think these destinations are based on how much there is to do and see in the area. This way you can get a better grasp on what destinations can be done in one day and which ones you may want to extend your trip on.

Day 1 & 2: Florence

A trip to Tuscany is incomplete if you don’t visit Florence. The cultural and artistic capital of Italy, Florence is a place where you could spend weeks and still not see all it has to offer.

Florence is the perfect place to kick off your Tuscany road trip as it is also the most convenient place from which to pick up a rental car/arrive in Tuscany.

Check out my guide to 2 days in Florence for specific ideas and tips on how to enjoy the city.

If you plan on staying in Florence longer and want a few day trip ideas up your sleeve, check out my favorite day trips from Florence.

Day 3: Panzano in Chianti, San Gimignano & Volterra

Medieval Italian village, Volterra
Volterra, Italy

After picking up your car in Florence, it is time to hit the road!

The first stops are just outside Florence at a maximum of an hour distance.

Pass first through the world-famous wine region of Chianti. If you are a wine connoisseur, you may already want to extend your trip a little to make time for a winery visit.

My favorite small town in the Chianti area is Panzano in Chianti. Here, you will find two amazing restaurants: the Antica Macelleria Cecchini (by famed butcher Dario Cecchini) and a place with an epic view, Ristorante Oltre il Giardino.

The other thing that makes Panzano so special is that it has a middle-of-nowhere feel, just completely surrounded by the rolling hills of vineyards.

Next, head over to the Medieval mecca of San Gimignano. San Gimignano is well-known for the “first skyscrapers”, as it is a town with many towers (insert how many towers in the past) One of my favorite areas is the castle ruins of Rocca di Montestaffoli.

Last but not least, pass through Volterra, another stunning Medieval village at the top of a panoramic hill.

Day 4: Pisa & Lucca

Italian plaza in the city of Lucca
Piazza Anfiteatro in Lucca

Continue heading west towards one of the world’s most iconic monuments. Arrive in Pisa and make your way through the lively town center to the Piazza del Duomo.

Here you can snap your iconic photo with the Leaning Tower of Pisa!

I personally didn’t find much else to do in Pisa, so I suggest you continue on the road to visit the quieter and charming Lucca.

Lucca is small but holds many treasures! The walled historic center feels like a storybook. Don’t miss walking on the walls, the unique oval-shaped Piazza Anfiteatro and the quirky Torre Guinigi, which has trees growing at the top of it!

Day 5 & 6: Orbetello & Porto Santo Stefano

The next day is a longer drive along an area that is often underrated by tourists: the Tuscan coast!

Because Tuscany is so famous for its iconic countryside landscape, I think many forget that Tuscany also has a huge coastline full of beautiful beaches.

So, if you are interested in seeing this hidden gem side of Tuscany, make your way to the peninsula of Orbetello. This is the area of the Monte Argentario, a place with some of Tuscany’s best beaches, like Feniglia Beach and Cala del Gesso.

Pro tip: If you have the time, I recommend staying at least 2 or 3 days in the area, as the main activity is going to the various beaches. So typically, you would go to a different beach each day.

Day 7: Saturnia & Pitigliano

Continue heading south to the very border of the Tuscany region.

Your first stop is going to be at the once hidden gem, now Instagram famous Saturnia hot springs. These springs are free to visit, in an extremely beautiful setting and they provide a relaxing, skin-nourishing benefit from the natural minerals.

After a bit of relax, head to what is one of my favorite towns in Tuscany. Pitigliano is right at the border of Tuscany and Lazio, so it has a really interesting Roman and Etruscan mixed history.

Moreover, it’s just simply beautiful. The town is known as the “Città del Tufo”, or city of rock, because it is literally coming out of the ground from this red clay rock above a steep valley. Read my full Pitigliano travel guide to find out the best things to do and see.

Day 8: Montepulciano & Pienza

Next, hit two of Tuscany’s classic wine country towns. These are villages you’ve likely heard of, whether you are an avid traveler or wine taster.

Montepulciano is a hilltop town that not only produces some of the world’s most famous reds but is beautiful to explore.

Make your way up to the cathedral at the top of the hill. If you get tired climbing the narrow streets, stop at the café for an iconic view at Caffè Poliziano.

And if you are going to do a wine tasting, Montepulciano is one of the best places.

Pienza, instead, is the gem of the Val d’Orcia, which is that iconic valley that you picture when someone says Tuscan countryside. It is also the home of Pope Pius II, so much of the town’s architecture and planning was influenced by him. In fact, it’s one of the first towns in which Renaissance architecture was implemented.

You can’t miss a stroll along the Via dell’Amore in Pienza, taking in the surrounding valley. Check out my full guide to Pienza.

Good to know: We had a great stay at Poggio Olivo, a stunning farmhouse in the Tuscan countryside. Not too expensive, amazing view and amenities and a very gracious host!

Day 9: Siena

Before you arrive in Siena, head to some of the best places to see cypress trees in Tuscany, like the Crete Senesi and the Cipressi di San Quirico.

Then head to Siena, one of the most beautiful small cities in Italy. From the terra cotta buildings to the unique Piazza del Campo to the breathtaking facade of the Duomo, Siena is just a seriously amazing place to discover with so much to see.

If you can, I would recommend staying 2 days in Siena. It is so beautiful and, while you can see most of the city in half a day, it would be best to give it at least a full day or two.

Day 10: Monteriggioni & Return to Florence

Medieval walled city in the middle of a field. Monteriggioni, Italy.

All good things must come to an end!

As you make your way back to Florence, stop by Monteriggioni, a 25-minute drive from Siena and a very unique, very small destination to close out your Tuscany road trip itinerary.

It is a Medieval walled town, one of the best preserved in the world. Entering the town is literally like entering a fortress of a different era.

The center is so small but still bustling. I had lunch here, a great Florentine steak at Ristorante da Remo.

Tuscany Road Trip Planning Tools & Tips

Renting a car & driving in Italy

One of the essential road trip tips I can help you with is on renting a car and driving in Italy.

Renting a car in Italy is straightforward and similar to other countries. The minimum age for rental is 26 years old. I prefer to use aggregator sites like AutoEurope that pull together all the different prices and options from various rental companies to find the best deal.

One thing you will definitely need is an International Driver’s Permit.

Pro tip: Keep in mind that the majority of vehicles in Italy are manual. If you cannot drive manual and prefer to drive a car with an automatic gearshift, you must specify this in your rental car reservation. Renting an automatic car typically comes at a higher cost.

Before you hit the open road, check out my guide to driving in Italy. There are quite a few differences and particular tips you should be aware of in order to avoid fines or any trouble!  

Calculating road trip cost

The resources I am about to share are some of my overall favorite road trip planning tips.

Budget is a huge part of planning a road trip and it can get out of hand if you don’t set up a plan beforehand.

One first step is to calculate the estimated cost of gas of your whole trip. Luckily, ViaMichelin makes this easy. It is one of my favorite tools to calculate the cost of different routes.

Input your destinations and the order in which you are visiting them to get an estimate gas price.

You should also use the site Autostrade, which is the website of Italy’s national highway system, as a resource for fuel prices, calculating your route and updated road information.

Also, use my free downloadable road trip budget planner to have an overview of all the main expenses that could come your way, beyond just gas and tolls! Just sign up below to my newsletter to get access to this free resource and many more in The Travel Library.

Locating gas stations is also a great resource for locating your nearest gas station or, if you are looking beforehand, the gas stations that are along your route.

You can just input where you are starting and where you are ending up, as well as add other specific parameters (like if you need regular gas, methane, diesel, etc) to get a list of the gas stations along the way.

Organizing your itinerary

Keeping your itinerary organized and handy isn’t as easy as it seems. That’s why I love Google Maps Trip Planner.

This tool allows you to create your own personal maps and separate the pinned locations by layer. You could separate them by category or, how I prefer, by day of trip, to see what’s the plan for each day of your itinerary.

It is also a great way to save extra ideas and stops in case you find yourself with extra time.

Learn how to make the most of using Google Maps Trip Planner for any of your travel itineraries!

The SGTD Take

I think it is obvious how I feel about a Tuscany road trip – it is one of the best road trips in Italy, a total dream and something I wish every traveler has the opportunity to do!

I was a “travel snob” who had been to Tuscany once and said, well what more could there possibly be? And now I have been several times after, always discovering something new and, of course, beautiful and charming.

There’s a reason it is one of the most popular destinations in the world and I must say, it deserves all the credit.

Italy Trip Planning Resources

  • Accommodation: For Italy, I mainly use to search and book places to stay.
  • Booking flights: I like to search for flights through Skyscanner, but I also book direct depending on the airline.
  • Activities & experiences: For things to do that require a ticket, and for more unique trip activities, I use Musement.
  • Road trip: For renting a car, I get the best prices by comparing companies with AutoEurope. I then use ViaMichelin to estimate road trip costs and to find gas stations/have live updates on traffic.
  • Transportation: Traveling by public transportation is a great way to see Italy. I use Trenitalia or Trainline to book tickets for trains and Flixbus for long-haul bus trips.
  • Accessories: I always travel with this portable charger to stay connected and with a universal adapter to accommodate Italy’s plug types.
  • Need help planning an itinerary? Fill out my form for a custom itinerary request!

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Plan your Tuscany road trip with me in the comments!




Michela is a travel writer and photographer living in northern Italy. She is passionate about helping people make the most of their travels by sharing advice gained from her personal experiences, off-the-beaten-path destinations and time-saving quick itineraries. Browse her top articles or have her help you plan your itinerary to your dream destination!

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