Tuscany By Car- Italy Road Trip Itinerary

May 23, 2020

Experience the best of Tuscany by car during this fascinating Italian road trip around Tuscany. Plan your perfect Italy road trip with Rentalmoose.

Click here for detailed directions

Summary (click the red pins for directions) :

Florence to Poppi- 60 kilometers (40 miles)đź“Ť  

Poppi to Arezzo- 40 kilometers (25 miles)đź“Ť 

Arezzo to Siena- 60 kilometers (40 miles)đź“Ť 

Siena to San Gimignano- 40 kilometers (25 miles)đź“Ť 

San Gimignano to Livorno- 80 kilometers (50 miles)đź“Ť 

Livorno to Pisa- 30 kilometers (20 miles)đź“Ť 

Pisa to Florence- 80 kilometers (50 miles)đź“Ť 

390 kilometers (240 miles) in total

Tags: Travel guide, Italy, Scenic Driving, History, Short Trip

The bucket list of every traveler. Picturesque cities full of historical landmarks, delicious cuisine, aromatic wine, scenic roads, and immaculate natural beauty. Tuscany has it all, and this travel guide takes you through the absolute best of it during an exciting Italian road trip.

This road trip itinerary takes you on a journey through the most scenic parts of Tuscany, exploring the best of what this region of Italy has to offer.

Begin with a day of sightseeing the historical landmarks in Florence, then let the scenic roads take you through hills and valleys off the main tourist tracks until you reach the peaceful towns of Poppi and Arezzo before arriving in Siena for the night.

On the second day, admire the “medieval skyscrapers” of San Gimignano and feel the Mediterranean breeze in the port town of Livorno. Later, make one last stop in Pisa before returning back to Florence.

How long does it take to complete this road trip?

The total driving distance is below 400 kilometers, with roughly an hour of driving between each stop.

That said, Rentalmoose recommends dedicating two days for this road trip, plus an extra day to explore Florence, at the very least.

To explore each spot thoroughly, add overnight stops in Siena and Pisa.

Road Trip Extensions

Northern Italy

Continue your Italian adventure even further and drive up north to Milan. Explore the fashion capital of the world, stroll down the streets of Lake Como, swim in the crystal clear Lake Garda, and more! Click here for the Northern Italy Travel Guide.

Southern Italy

You can also extend the adventure and explore the picturesque Southern part of Italy. Drive across the Amalfi Coast, go beneath the ground and hike in the eerie catacombs in Naples, or relax at one of the pristine beaches. Check out the Rentalmoose Southern Italy Travel Guide.

When is the best time to visit Tuscany?

The best time to visit Tuscany is right before and directly after the tourist season peaks in the summer.

Consider going on this trip between April and May or September and October, when you can still enjoy a bit of the summer weather without massive crowds.

The weather is the hottest between June and August, but it is also the peak of the tourist season.

Why should I book a rental car in Tuscany?

Tuscany is one of the best destinations to pick for an Italian road trip. Some of the less popular destinations, such as Poppi or Arezzo, lack a convenient public transport connection. What’s more, there are tons of spots between the suggested stops that are waiting to be discovered, including local villages and scenic vineyards.

The roads are also well-developed and offer spectacular views along the way. What more could a road trip lover ask for?

When driving in Italy, keep in mind that it is common for others to squeeze into extremely tight parking spots. An occasional scratch here and there could happen, therefore Rentalmoose recommends adding excess coverage when booking your rental car in Tuscany.

Once you’ve picked up the car, don’t forget to take photos of the car to qualify for a 50% discount from the excess coverage fee.

Can tourists drive in Italy? 

Absolutely! Tourists in Italy need an International Driving Permit to drive here unless they have an EU-issued domestic license. These can easily be obtained in your local country and are mandatory for non-EU driver licenses when driving in Italy.

Where can you get an International Driving Permit? How much does an IDP cost? Check out this blog post to learn all you need to know regarding International Driving Permits.

Driving in Italy for the first time might be quite a hectic experience. Getting around large cities is chaotic and driving around tight cobblestone streets can be a nightmare.

On top of all this, the locals don’t really seem to be following the speed limits.

Speeding is common among drivers in Italy. Tourists in Italy have to pay the fine on the spot to the police and can additionally be charged by the car rental company. 

Going up to 21km/h over the limit on the highway will cost you around 150 Euros, while breaking a “no-parking” rule will cost you around 80 Euros.

Traffic in Italy is on the right-hand side of the road.

Now that you’re all set, let’s dive into this exciting Italy road trip!


florence skyline city view from above during sunset colorful basilica and mountains in background. See Florence during our Italy road trip itinerary around Tuscany

Photography by Meipakk/Pixabay.com

Your Italian road trip across the incredibly picturesque region of Tuscany begins in an equally charming city of Florence. Despite its size, Florence feels like a little welcoming village. Rentalmoose recommends spending at least a day in this fascinating city before departing further.

For maximum convenience, pick up your rental car directly at the Airport of Florence. Car rentals that support airport pick-up can be found via Rentalmoose.

Once you’ve got your car, it’s time to explore Florence!

What is Florence famous for?

Galleria Dell’Accademia

Florence, like all of Italy, has an extremely rich history which is reflected in the region’s attractions.

When in town, you can’t skip the Galleria Dell’Accademia, a world-class gallery that hosts some of Europe’s most precious artwork.

While the museum is home to some admirable Florentine paintings from the 14th and 15th centuries, the undebatable highlight is the “David” statue created by Michelangelo.

The iconic statue has made the Galleria Dell’Accademia the most frequently visited museum in Florence, it’s best to book your tickets online ahead of your visit. 

Driving in Florence- ZTL Area

Driving within Florence can get very expensive if you don’t pay attention to the road signs. The historic center of the city is a UNESCO World Heritage Site. For this very reason, the heart of Florence is a part of the ZTL area.

What is the ZTL area, you ask? You can only drive inside with a proper permit (it’s very likely that your rental car won’t come with one). If your hotel is within the ZTL, you may come in for a limited time in order to unload your car. In that case, be sure to let your hotel know that you’re arriving by car.

What is the best car park in Florence?

Santa Maria Novella

The best place to park your rental car is at the Santa Maria Novella train station. Drop your car off for roughly 2-3 Euros per hour and stroll down to the city center.

Florence Cathedral

Head to the monumental Cathedral, the third biggest church in the entire world. Observe the decorative facade that dates back to the late 13th century, or step inside and explore the interior of the historical structure.

Admission to the Cathedral itself is free of charge, but you will need to purchase a ticket to access the nearby museum, baptistery, dome or bell tower.

Ponte Vecchio

Walk south from the Santa Maria del Fiore Cathedral for roughly 10 minutes until you reach Ponte Vecchio, the oldest bridge in Florence connecting two banks of the Arno river.

The bridge has been a symbol of the city for centuries. The present Ponte Vecchio was constructed in the 1300s after a flood destroyed its previous version, though the initial Ponte Vecchio dates back as early as the 900s. 

Today, the bridge is a vibrant tourist hotspot lined with cute souvenir shops and prestigious jewelers, where you can purchase some glamorous Florentine necklaces, rings and more.

Trattoria Sabatino

Visit the Trattoria Sabatino for a traditional Italian dining experience. The eatery has been serving delicious regional dishes ever since it first opened in 1956 and has become one of the favorites among locals and tourists.

The family-run trattoria is surprisingly affordable, too. You can order a meal for less than 5 euros.

Where can you stay in Florence?

Luxury travelers should consider staying at Villa La Vedetta, a prestigious 5-star villa-turned-hotel near Florence. Choose from one of the elegant rooms and suites, relax at the outdoor terrace that overlooks the city or go for a dip in the outdoor pool. The hotel’s incredible restaurant is worth mentioning, too.

Traveling on a budget? The city is scattered with unique hotels that are relatively affordable, keeping in mind that Florence is one of the most expensive cities to visit in Italy.

That said, consider booking a room at the historical Palazzo Guadagni. The 3-star hotel is situated in a palazzo that dates back to the early 1500s and is just a walk away from Ponte Vecchio. Elegant rooms and great service aside, the hotel’s Loggia roof bar offers sensational views of the city.

Next on your Italy road trip: Poppi, 1 hour 20 minutes


medieval tower and buildings in poppi town surrounded by trees and green fields in tuscany italy on a cloudy day

Photography by Joakant/Pixabay.com

Depart Florence and follow the scenic SR70 route across the endless greens. After a little over an hour, you will reach the charming village of Poppi.

Is Poppi worth visiting?

Poppi is a tiny village with less than 10000 inhabitants, hence it is often overlooked by tourists traveling around Tuscany. The reality is that the cute village is definitely worth visiting, especially to see its historic castle without hordes of tourists.

Castello dei Conti Guidi

The winding streets will take you to the Castello dei Conti Guidi, a local landmark in Poppi. The 13th-century castle remains very well-preserved and can be explored both inside and out. The top of the tower opens up to panoramic views of the town and its scenic surroundings, making a perfect photo opportunity.

Open daily until 6 PM.

Badia San Fedele

After exploring the castle, make your way to the Badia San Fedele just a stroll away. The historic abbey was home to monks from Vallombrosa and was constructed back in the 10th century.

Today, it is one of the most significant landmarks in the Casentino valley. The structure is also filled with precious artwork which is worth at least a quick peek. The peaceful church is the perfect spot to simply relax and enjoy the silence.

Gelateria Paradice

No trip to Italy would be complete without an ice cream stop in a local gelateria (Italian ice cream cafes), and Poppi happens to be home to Gelateria Paradice, one of the best in the Casentino valley.

Open between 11 AM and midnight, closed on Mondays.

Next on your Italy road trip: Arezzo, 40 minutes


empty piazza grande main square in italy well in foreground and medieval  buildings in background during sunrise in arezzo italy

Piazza Grande photographed by Elena/Pixabay.com

The 40-minute drive from Poppi, though not the most scenic in this journey, is immensely fun. Follow the winding roads of SP70 and SP71 until you reach Arezzo, another sweet Italian town worth visiting.

What can you do in Arezzo?

Piazza Grande

Observe the life of the city at Piazza Grande, the true heart of Arezzo. Admire one of Tuscany’s best-preserved medieval squares, surrounded by colorful buildings full of local eateries and shops.

The cozy streets around the square make it the perfect spot to wander around and discover local treasures.

Cinema fans will likely recognize Piazza Grande, as the opening scenes of “La Vita E Bella”, the 1997 award-winning film by Benigni, were shot right here. 

Arezzo Antique Fair

Take part in the famous Arezzo Antique Fair, one of the biggest fairs of this kind in Italy. The fair attracts hundreds of exhibitors from across the country. Stroll around the fair, as there are thousands of antiques, including priceless books, artwork, and jewelry.

The fair takes place every first Sunday of the month and the Saturday before.

Arezzo Cathedral

Don’t forget to drop by the 15th century Arezzo Cathedral. Admire the well-preserved medieval facade or step inside the monumental building, where you will find beautifully painted ceilings, the Gothic tomb of Guido Tarlati and a precious portrait of Mary Magdalene.

The Piazza del Duomo by the cathedral is the perfect spot to photograph the panoramic views of Arezzo, as it is the highest point in town.

Admission to the church is free of charge.

Next on your Italy road trip: Siena, 1 hour


torre del mangia red brick medieval tower symnetrical photo seen from nearby square in siena italy

Photography by Samuele Schiro.

The historic center of Siena is a UNESCO World Heritage Site. Similarly to Florence, this part of the town can’t be accessed by car as it is a ZTL area.

Rentalmoose recommends leaving your car at the private Il Campo Car Park, located within walking distance of the center of Siena. There are nearly 600 spaces available and the hourly rate is around 2 Euros.

Piazza del Campo

Once you’ve left your car, walk to the monumental Piazza del Campo. The unique shell-shaped square serves as the heart of the city ever since it was first constructed in the 13th century.

Feast your eyes on the well-preserved historical buildings or pop by the local cafes and eateries. The fact that the square is less busy than the heart of Florence makes the streets of Siena even more enjoyable to get lost in.

Palio di Siena

Piazza del Campo is turned into a horse racetrack and the famous Palio di Siena race takes place two times every year. The highly anticipated race is the biggest event in Siena, and one of the most significant gatherings in the entire country.

Check the official website for the schedule and more details on ticketing.

Torre del Mangia

Travelers can, and quite frankly should, climb the stairs to reach the top of Torre del Mangia. The monumental tower stands 87 meters above the ground and provides some of the best spectacular views in all of Tuscany.

Keep in mind that you have to cover 400 steps to reach the top. The journey to the top can get tiring, but the views are absolutely worth it!

La Taverna di San Giuseppe

All the sightseeing will probably drain your energy, visit La Taverna di San Giuseppe for a lunch stop. The menu is made up of lots of regional dishes from Tuscany as well as other parts of Italy.

Try some of the locally-made, fresh pasta or choose from a selection of Italian wines. The delicious cuisine was appreciated by critics and has earned the restaurant a spot in the Michelin guide.

Siena is packed with historical sites waiting to be explored, that’s why Rentalmoose recommends making at least one night stop in this history-filled city.

Looking for the ultimate luxury hotel near Siena?

Consider booking a room at the Castel Monastero. The prestigious 5-star resort is situated in a renovated monastery around 20 kilometers east of Siena. Choose between elegant rooms and suites, relax in one of the three outdoor pools or enjoy a massage in the spa and wellness center.

Castel Monastero is the go-to secluded getaway in the heart of the Tuscan countryside.

An affordable alternative in Siena would be the Relais la Corte Dei Cavalieri. The 3-star hotel features classy rooms, free wi-fi and a perfect location near the heart of Siena. Keep in mind that the hotel doesn’t provide a private car park for guests.

Next on your Italy road trip: San Gimignano, 50 minutes

San Gimignano

medieval brick towers in sam gimignano skyline city view from a distance and green tuscan fields landscape in foreground

Photography by SilvanoCosta/Pixabay.com

The next stop on this Italian road trip is San Gimignano, a wonderful town known as “The City of Towers”. Over 70 towers were constructed here in the 12th century. Sadly, just 14 remain today, though the site remains spectacular nonetheless.

Is San Gimignano worth a visit?

Sam Gimignano is quite literally the embodiment of Tuscany: a historical hilltop town surrounded by green vineyards and fields. If you’re on a road trip through Tuscany, you simply can’t skip it.

Scenic old architecture in Sam Gimignano, often called the medieval manhattan, a small town in Florence Italy. See it during our Italy road trip itinerary around Tuscany
San Gimignano at night is unbeatable.

Torre Grossa

As the town is known for its 14 dramatic towers (a sort of medieval skyscrapers, if you will), the only way to begin exploring it is by climbing the highest one of them.

Head to the Torre Grossa, the 54-meter tower was built in the 1300s and is proudly representing the city to this day. The climb, similarly to Torre del Mangia in Siena, is quite lengthy. Just like in Siena, the rewarding views from the top make the effort absolutely worth it.

A 2-day admission pass costs below 10 Euros per person and includes access to all museums in town.

Gelateria Dondoli- the best Gelato in San Gimignano

Try the city’s best gelato (Italian ice cream) at the Gelateria Dondoli. The award-winning ice cream parlor remains one of the favorites among locals, the frequent lengthy queue proves it. Gelateria Dondoli is conveniently situated near the heart of town along Piazza della Cisterna.

The Gelateria also offers ice cream classes, during which you will be taught to make your own delicious gelato. Click here for more details.

Gelateria Dondoli has the best gelato in San Gimignano, perhaps the best gelato in all of tuscany. Gelato is Italian ice cream.

La Rocca

San Gimignano is famous around the world for its aromatic white wine, the Vernaccia di San Gimignano. Head to La Rocca for a one-of-a-kind wine experience. Discover the history of the region’s wine during a fascinating interactive exhibition.

Of course, guests can try the wine as well, or book a more-detailed guided tour. Find all of the details on the official website.

Next on your Italy road trip: Livorno, 1 hour 20 minutes


rocks on livorno coast calm sea and coastside building during sunset in tuscany italy

Enrico Nunziati/Pixabay.com

After exploring the hills and never-ending greens of Tuscany, it is time to head to the coast. Drive for around an hour and twenty minutes until you reach Livorno, a port town along the western coast of Italy.

What is there to do in Livorno?

Terrazza Mascagni

Feel the breeze of the Mediterranean as you wander down the Terrazza Mascagni, a wide waterfront terrace in the southern part of the city. The area acts as a promenade and is a favored hangout by locals.

On-street parking is available on the main road right by the waterfront.

Observe the sun setting over the horizon or pay a visit to the nearby Livorno Aquarium. Examine the exotic sea creatures daily from 10 AM. Admission to the aquarium costs up to 17 Euros per person. 

New Venice

Did you know that Livorno has its own Venice? In the 1620s, the city desperately needed an expansion plan. The area between the existing districts was separated by moats, the architect’s workaround was copying Venice’s design and using waterways instead of roads. The newly designed district was then named “New Venice”.

Today, it is one of the most picturesque parts of the city. Take a boat tour or stroll around the neighborhood on foot.

Don’t miss the Fortezza Nuova, a historic fortress in the heart of the district.

La Perla dell’Ostricaio

As you are in a port town afterall, it only makes sense to try some fresh local seafood for lunch. Head to La Perla dell’Ostricaio, one of the best seafood restaurants in Livorno just a walk away from Terrazza Mascagni.

Rentalmoose order tip: Try the locally-caught fish, shrimps or octopus.

Open all week between noon and 3 PM for lunch, then between 7 PM to midnight for dinner. 

Grand Hotel Palazzo Mgallery Livorno illuminated by the sunset. the best 5 star luxury hotel in Livorno italy
La Perla Dell’Ostricaio is located at the beautiful Grand Hotel Palazzo MGallery. Looking for the best hotel in Livorno? Spend the night here.

Next on your Italy road trip: Pisa, 30 minutes


The famous leaning tower of Pisa in Pisa, Italy. The tower can be seen during our Italy road trip itinerary around Tuscany

Is Pisa worth visiting?

A short 30-minute drive will take you to Pisa, the city that’s home to the famous Leaning Tower of Pisa, along with other historical treasures. As overcrowded as the city gets during peak tourist season, its landmarks are certainly worth visiting.

Where to park in Pisa?

Via Camneo

Rentalmoose recommends dropping off your car at the Via Camneo private car park, just a short stroll away from the Leaning Tower of Pisa. The car park, as of 2020, costs 2 Euros per hour.

Another major historical town in Italy means more inaccesible ZTL areas. Be cautious not to enter the limited-access center of Pisa, or you might end up paying a hefty ticket.

The Leaning Tower of Pisa

Once you’ve left the car, walk towards the Leaning Tower of Pisa, one of the most significant landmarks in the entire world. Admire the monumental tower from Piazza del Duomo, a photo of you holding up the leaning tower is a must, too!

For around 20 Euros, travelers can climb the stairs atop the tower for the best views of Pisa. Lots of people want to do it, so expect long queues. 

The Cathedral

Walk across the Piazza del Duomo to the massive Cathedral. In fact, it was the biggest church in Europe at the time of its opening in the 14th century. You can admire the well-preserved, decorative interior completely free of charge, too.

The cathedral is surrounded by beautiful green lawns, where you can sit down and relax after all the driving all while admiring the heart of Pisa.

Baptistery of San Giovanni

Another major landmark along the Piazza del Duomo is the Baptistery of San Giovanni. The round structure dates back to the 1100s and stands at over 50 meters above the ground.

The monumental building blends in together with the equally beautiful Cathedral and, of course, the Leaning Tower of Pisa.

Ristorante Le Bandierine

Once you get hungry, be sure to visit the Ristorante Le Bandierine. One of the best regional restaurants in Pisa, Le Bandierine is especially famous for its incredible spaghetti dishes.

The restaurant is just a walk away from the Arno river, which is another spot worth visiting when in Pisa.

Le Bandierine is open daily for dinner between 7:30 PM and midnight.

Next on your Italy road trip: Florence, 1 hour 10 minutes


Drop off your car at the Florence Airport right where you picked it up. Browse through car rental companies that support airport drop-off via Rentalmoose. Don’t want your Italian adventure to end? Extend the trip to the North of Italy, or the stunning Southern Coast.

Don’t forget to book your rental car via Rentalmoose for your next road trip in Italy. On our platform, you can find the top rental companies at the best price, along with tens of curated travel guides around the globe. Get your car from Rentalmoose!

We plant a tree for every booking made with our platform.

Post your pictures from your next road trip in Italy online using #Rentalmoose! Our favorite ones will be featured in the upcoming blog posts.

Rentalmoose OĂś 2020

You Moose See This Deal!

Sign up for our newsletter to save 30% on your next rental car booked via Rentalmoose. Be the first to hear about exclusive deals, the latest travel guides, and more.

P.S. We keep your data private and promise not to spam.