A Tuscan Road Trip Itinerary From Florence: Highlights & Tips

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Tour your way through the best small towns and natural wonders along this Tuscan road trip route (beginning in Florence).

The best way to visit Tuscany and really see Tuscany is with a car. To reach the iconic medieval walled towns in Tuscany, the breathtaking countryside and to experience some of the most beautiful roads in the world, can all be accomplished by road tripping.

Drive your way through Tuscany with this ultimate Tuscan road trip itinerary which will allow you to see the region’s many beautiful highlights, all on your own schedule.

Plan your own adventure with this self guided driving tour of Tuscany which starts and ends in Florence.

From picturesque hilltop villages to natural wonders, this ultimate Tuscany road trip route suits any eager explorer looking to truly discover Toscana.

Quick List: Tuscan Road Trip Highlights

• San Gimignano
• Terme di Saturnia
• Lucca
• Cortona
• Pisa
• Val d’Orcia
• Pitigliano
• Volterra
• Monteriggioni

Wait, Where is Tuscany?

All this talk about Tuscany can make one wonder “Do I even really know where Tuscany is?” The good news is, you’re definitely not alone in this.

Whether some can admit it or not, finding Tuscany on a map isn’t straightforward for everyone. The most important thing to know about Tuscany is that Tuscany is not a city or town. Tuscany is a region in Italy.

The region is made up of multiple provinces including Firenze, Grosseto, Lucca, Pisa, Arezzo and more. Often times, this is when it gets the most confusing for tourists because they’ll hear the names of provinces all while pondering if they left Tuscany without knowing it.

The region of Tuscany is situated in central Italy, just north of the Lazio region which is where Rome is located. The landscape is most notably famous for its lovely scenery comprised of rolling hills, cypress trees, endless wine and olive groves.

In this particular guide, we’re slightly cheating and including one or two highlights just outside of the Tuscany region.

The neighbouring areas of Umbria and Lazio share regional borders with Tuscany and naturally have many places to see that are just as stunning. Umbria in particular is often grouped with Tuscany as they share many similar traits.

It’s up for debate but Umbria is perhaps even slightly more enjoyable due to the smaller number of tourists it receives compared to Tuscany.

Where to Start a Road Trip to Tuscany

For travellers interested in taking a Tuscan road trip, it makes the most sense to fly into Florence (also named Firenze in Italian). This allows for visitors to experience the very heart and capital of the Tuscany region, in addition to being the most efficient road trip starting point.

By beginning your Tuscan road trip in Florence, you’ll be able to complete a loop of the Tuscany region below Firenze.

Starting and ending in the same location is key for a successful road trip if you are flying and renting a car.

If you are not flying into Florence, this Tuscan road trip can still be accomplished without making a loop.

Instead, travelling through Tuscany from north to south or vice versa is also feasible. Particularly for those looking to make a trip from Rome to Florence, driving through Tuscany starting the bottom to the top is absolutely ideal. 

Itinerary Overview: Self Guided Driving Tour of Tuscany

• Day 1
  • Explore and sleep in Florence
• Day 2
  • Pickup a rental car and drive from Florence (possible stop at the Mall Firenze) to Cortona (1.5 hours)
  • Explore Cortona
  • Sleep in Cortona
• Day 3
  • Drive from Cortona to Lago Trasimeno (25 minutes)
  • Explore Parco Regionale del Lago Trasimeno
  • Drive from Lago Trasimeno to Panicale (20 minutes)
  • Explore Panicale
  • Drive from Panicale to Orvieto (1 hour)
  • Explore and sleep in Orvieto
• Day 4
  • Drive from Orvieto to Civita di Bagnoregio (30 minutes)
  • Explore Civita di Bagnoregio
  • Drive from Civita di Bagnoregio to Pitigliano and Sovana (1 hour)
  • Explore and sleep near Pitigliano or Sovana
• Day 5
  • Drive from Sovana to Terme di Saturnia (30 minutes)
  • Visit Terme di Saturnia in the morning, in attempt to beat the crowds
  • Drive from Terme di Saturnia to Orbetello (1 hour)
  • Explore Orbetello
  • Drive from Orbetello to Montepulciano (2 hours)
  • Explore Montepulciano
  • Drive from Montepulciano to Val d’Orcia / Crete Senesi (30 minutes)
  • Explore and sleep in the Crete Senesi area
• Day 6
  • Drive from Val d’Orcia to Buonconvento (30 minutes)
  • Explore Buonconvento
  • Drive from Buonconvento to Abbazia di Monte Oliveto Maggiore (15 minutes)
  • Explore Abbazia di Monte Oliveto Maggiore
  • Drive from Abbazia di Monte Oliveto Maggiore to Monteriggioni (1 hour)
  • Explore Monteriggioni
  • Drive from Monteriggioni to Volterra (45 minutes)
  • Explore and sleep in Volterra
• Day 7
  • Drive from Volterra to San Gimignano (40 minutes)
  • Explore San Gimignano
  • Drive from San Gimignano to Pisa (1 hour and 15 minutes)
  • Explore Pisa
  • Drive from Pisa to Lucca (30 minutes)
  • Explore and sleep in Lucca

Map of Highlights: Tuscan Road Trip

Tuscan Road Trip: Top Places to Visit

There are many “must see” places in Tuscany which we’ve separated from the lesser known gems. Depending on how much time you have, you can choose to see just the most popular sites in Tuscany or extend your road trip to discover some remarkable wonders off the beaten path.

San Gimignano

Distance from Florence: 1 hour drive (60 km / 37 mi)

One of the most charming medieval towns near Florence is San Gimignano. The village is small and especially famous for its 13th-century fortress walls which now keeps the historic center for pedestrians only.

What sets San Gimignano apart from many other hilltop towns are the surviving and preserved tower houses that make up the village’s skyline.

This town has earned the title of being a UNESCO World Heritage Site for more than 30 years thanks to the beautifully conserved original architecture.

Cascate del Mulino di Saturnia (Terme di Saturnia)

Distance from Florence: 3 hour drive (191 km / 118 mi)

Lately, it seems like you cannot escape seeing photos of the famed Terme di Saturnia in Tuscany. Its recent growth in popularity is not surprising as the site is a spectacular wonder to see and experience. Possibly more importantly, it’s free to visit.

The site is comprised of natural sulphurous thermal springs, known for their healing benefits. Since the hot springs are no longer a secret, it gets crowded, even if you arrive very early in the morning.

Unless you are lucky or visit in the winter, you should come to terms with the fact that you won’t be the only one at the bath.

There is also a huge parking lot for visitors, convenient for making this a Tuscan road trip stop.

Lucca

Distance from Florence: 1 hour and 15 minute drive (95 km / 60 mi)

As a popular day trip from Florence, Lucca is one of the larger cities in Tuscany and is filled with many historic attractions.

The entire city is a circular shape but the most noteworthy characteristic of Lucca is its Piazza dell’Anfiteatro. Town squares are usually, squares. However, Lucca’s plaza is oval shaped as it used to be a Roman amphitheater.

Nowadays, it’s aesthetically lined with cafes and restaurants. Ancient Renaissance walls, cobblestone alleys and beautiful churches are what make Lucca one of the most frequented highlights in Tuscany. 

Cortona

Distance from Florence: 1.5 hour drive (116 km / 72 mi)

Situated in the province of Arezzo, Cortona has rightfully earned the right to being one of the most endearing towns in Tuscany. The hilltop town is classically wrapped in a medieval wall and filled with bewitching old streets, a cafe filled town centre and historic landmarks.

Cortona is an important detail in the history of the ancient Etruscan civilisation and even has a museum dedicated to this.

To catch a sunset and panoramic views, head to Basilica di Santa Margherita and walk towards the back of the church. You’ll find a terrace overlooking the towns, countryside and lake below.

Leaning Tower of Pisa

Distance from Florence: 1.5 hour drive (98 km / 60 mi)

If seeing the renowned leaning tower of Pisa is on your bucket list, you cannot complete a Tuscan road trip without a visit.

The tower has been known to survive a number of strong earthquakes which means it’s likely not tipping over any time soon. Still, best to see it in the near future and not take the chance.

The leaning tower of Pisa is part of the UNESCO Site which also includes the Cattedrale di Pisa within the same plaza.

Entering the vicinity of the cathedral and tower’s locations is completely free to do but going inside the buildings requires tickets.

Val d’Orcia

Distance from Florence: 2 hour drive (121 km / 75 mi)

To capture the ultimate photo of the Tuscan countryside, you should not miss driving through Val d’Orcia and its surroundings.

Between the villages of San Quirico d’Orcia and Pienza is where you’ll find many opportunities for the perfect shot of rolling hills, cypress hills and that quintessential Tuscan feel.

As always, it’s important to remain respectful and not cross any private property which includes farm land.

Below are some exact locations for a classic photo of Tuscany:

• Viale di Cipressi
• Crete Senesi Vista
• Gladiator Shooting Spot
• Cypress Road

🥾 Read More: Two Great Hikes in Val d’Orcia

Pitigliano

Distance from Florence: 3 hour drive (190 km / 118 mi)

Known as “The Little Jerusalem,” Pitigliano was once a refuge for Jews in the Tuscany region and even Rome. Unlike other medieval establishments, Pitigliano sits along a ridge and not on a hilltop. Thus, creating one of the most iconic and dramatic town skylines.

When viewing the town from afar, it looks like Pitigliano can come sliding straight down after a heavy rainfall but it’s managed to stay put for more than 3,000 years.

Volterra

Distance from Florence: 1.5 hour drive (81 km / 50 mi)

Another town with ancient city walls that should not be missed during your Tuscan road trip is Volterra. The town is drenched in history and has some fantastic museums and landmarks to show for it.

One notable site includes the ruins from a 3rd-century Roman bath. Within the city’s current town hall, you can even still view medieval frescoes on the walls. There is not one, but two ancient Roman theatres to be visited, countless significant towers and remarkable churches.

Parking tip: There are many access points to Volterra, some easier than others. The best place to park for free is here.

Then, walk up the set of stairs after passing through the Porta e Fonti di Docciola landmark.

Lesser Known Gems of Tuscany

Panicale

Distance from Florence: 2 hour drive (135 km / 83 mi)

The town of Panicale is so small that if you blink, you may miss it during your road trip. Panicale is comprised of a loop with only a handful of streets which go around it. Its micro size lets you appreciate and hone in on every last detail, something that can get difficult to do when you’re in a large city.

Panicale’s town square is idyllic and reminds us of stepping onto a movie set. There are also only a handful of places to eat which makes deciding on a meal that much easier. It is the perfect Tuscan road trip itinerary item because of its manageable size and convenient park lot, allowing you to quickly yet thoroughly spend some time here.

Lake Trasimeno Regional Park

Distance from Florence: 2 hour drive (121 km / 75 mi)

Trasimeno Park rarely makes the list for Tuscan itineraries but it’s unquestionably worth visiting. The regional park features a 32,000-acre lake with islets you can actually stay the night on.

Aside from being a haven for wildlife and birdwatchers, it’s an unspoiled place to visit off the beaten path in Tuscany.

Take your pick of the many delightful villages which sit on the lakefront such as Castiglione del Lago. Each small town has their own waterfront promenade, ideal for an afternoon stroll.

For lunch, do not miss Faliero Torta d’la Maria on the south side of Lake Trasimeno. They serve phenomenally uncomplicated yet exquisite Tuscan style food. No frills, just a really good meal.

Orvieto

Distance from Florence: 2 hour drive (165 km / 102 mi)

As somewhat of an archaeological marvel, the historic town of Orvieto is especially ideal for those interested in Etruscan heritage. Orvieto offers not only a 16th-century well shaft to be seen but an entire underground tunnel system, once believed to be separate city.

The massive clock tower is also hard to miss as you approach Orvieto and boasts the best panoramic view after a 250-step climb.

Sovana

Distance from Florence: 3 hour drive (184 km / 114 mi)

Sovana is a village containing one single main street. During the summer, this street is blissfully decorated with plants and flowers. There are only a handful of hotels or guesthouses, cafes and shops which sell gelato.

Near one end of the town, you’ll find Cattedrale dei Santi Pietro e Paolo, the village’s church. Sovana is by no means a hot tourist destination and that is exactly what makes it one of the most genuine places to visit in Tuscany.

For a break from the crowds and tour groups, this will undoubtedly be the most peaceful stop during your Tuscan road trip.

Civita di Bagnoregio

Distance from Florence: 2 hours and 15 minutes drive (181 km / 112 mi)

Technically speaking, Civita di Bagnoregio is not in Tuscany but in the Lazio region instead. Specifics aside, it should without a doubt be included on any itinerary for Tuscany because it is so exceptional.

What makes it so special? The village of Civita di Bagnoregio is only accessible to tourists with a pedestrian bridge which connects the hilltop settlement to the mainland town of Bagnoregio. Think of it as an island, but on a cliff!

The views are marvellous, the historic architecture is extraordinary and you only need to spend one hour exploring. For a road trip stop, you really couldn’t ask for much better.

La Balena Bianca

Distance from Florence: 2 hour drive (150 km / 93 mi)

Visiting La Balena Bianca (or the The White Whale) is by far the best alternative to Terme di Saturnia. Since it does require a short hike, it’s a little less accessible and therefore attracts a crowd that’s willing to walk to it.

It is also not completely free if you need to park in the designated lot but the parking fee is under €2 per hour. Surrounded by a lush green forest, the atmosphere of this warm sulphur bath is also much different than that of Saturnia but equally as stunning.

Orbetello

Distance from Florence: 2.5 hour drive (191 km / 118 mi)

It’s easy to forget that Tuscany actually has a coastline. Although it’s not made up of the most beautiful beaches in Italy, it’s still worthwhile to visit.

Monte Argentario is one of the most mysterious pieces of Italian soil and it’s located on the coast of Tuscany. The quasi-island is connected by two narrow strips of land plus a bridge leading from Orbetello.

Most of the island is not developed which makes it a unique road trip stop for those seeking an adventure. 

Orbetello itself is an interesting town to visit as it sits among a large marshland and lagoon. The most prominent landmark of Orbetello is the Ancient Spanish Mill, unassumingly emerging from the water.

The main motorway along the seacoast also makes it quick to shoot back up north after visiting Orbetello during a Tuscan road trip.

Montepulciano

Distance from Florence: 1.5 hour drive (109 km / 68 mi)

Located in the province of Siena, this hilltop village is surrounded by vineyards and more vineyards. Wine enthusiasts, do I have your attention now?

You may have heard of Montelpulciano by simply perusing the beverage section at any Italian supermarket. For wine tasting in particular, a stop in this town to enjoy the renowned Vino Nobile di Montepulciano is highly recommended as part of a Tuscany itinerary.

Buonconvento

Distance from Florence: 1.5 hour drive (101 km / 62 mi)

Although it’s not a town which is perched on a hill or cliffside, Buonconvento deserves attention. It is a small, yet pleasant village in the province of Siena and furthermore, in the scenic area of Crete Senesi. Yet, it often gets passed up by visitors who end up missing out on Buonconvento’s small town magic.

There are only a handful of streets which make up the old town centre but each corner is carefully curated. Boutique shops, antique stores and cute cafes fill the main pedestrian street of Via Soccini. 

Abbazia di Monte Oliveto Maggiore

Distance from Florence: 2 hour drive (112 km / 69 mi)

Abbazia di Monte Oliveto Maggiore is a monastery, buried in the heart of a green forest and hidden from plain sight. Whether you’re interested in religious sites or not, the astounding position of this monastery is for anyone to appreciate. Originally founded in 1313, original works of art and religious artefacts are available to see at this working complex.

Monteriggioni

Distance from Florence: 1 hour drive (62 km / 38 mi)

Monteriggioni is whimsically bite-sized! It’s a fortress walled village with remaining medieval landmarks and a sprawling town square, but really not much else. Is the lack of things to do a reason to not visit Monteriggioni? In fact, it’s the exact opposite!

With a couple of restaurants, some of the best gelato in Tuscany and a convenient parking lot, it’s a fantastic road trip itinerary item despite its modesty.

Monteriggioni somehow manages to capture the complete energy of Tuscany and delivers it to visitors in a small yet sensational package.

The Mall Firenze and Prada Outlet

Distance from Florence to The Mall Firenze: 40 minute drive (34 km / 21 mi)

Distance from Florence to Prada Outlet: 45 minute drive (51 km / 31 mi)

A bit of an unconventional road trip itinerary item but since you’re in Italy, you might as well stop at a luxury shopping outlet. The Mall Firenze is especially close to Florence and somewhat of a major destination with tour buses regularly filtering in and out of Florence to get there.

For discount deals on brands like Gucci, Fendi, Givenchy and more, The Mall Firenze is a must. The Prada Levanella Outlet is a bit further south and is the absolute best place in Italy to shop some Prada.

Who says a Tuscan road trip can’t include some retail therapy?

Where to Stay During Your Road Trip in Tuscany

Florence – Night 1

Hotel Nella or B&B Stupido Hotel

Cortona – Night 2

Monastero San Silvestro or La Renaia

Orvieto – Night 3

Casa Vèra Affittacamere or Agriturismo Podere Pescara

Pitigliano or Sovana – Night 4

La Casa all’Oliveto or PoggioBa

Crete Senesi – Night 5

Agriturismo Podere San Gregorio or Casa Vacanze San Pierino

Volterra – Night 6

Appartamenti Villa Mascagni or Il Portone Apartments

Lucca – Night 7

Agriturismo Ai Linchi or Ospitalità Rurale l’Uccelliera

How Many Days Do You Need for a Road Trip in Tuscany?

Considered one of the best road trips in Italy, you can easily spend an entire month touring Tuscany by car. Since we know this isn’t a realistic option for most, we’ve compiled a suggested road trip itinerary for Tuscany which will take one week.

With a week long road trip through Tuscany, you’ll be able to see a number of popular sites in addition to lesser known gems.

If you are short on time, there are a handful of Tuscan sights in this guide which you can choose to omit. By doing so, you can focus on visiting the most admired places in Tuscany with a 3-4 day road trip instead.

The time you need to visit Tuscany will ultimately depend on what you prefer to see the most of. Whether it’s the Tuscan countryside, medieval hilltop towns or wine tasting, it’s best to prioritise what you enjoy most before putting together a Tuscan road trip itinerary.

This will easily determine how many days you need in Tuscany in order to fit everything in.

Getting Around During Your Tuscany Road Trip

The first essential key to a beautiful road trip in Tuscany is unsurprisingly, the car. For a self guided driving tour of Tuscany, you’ll need to get around with your own car or a rental car.

Fortunately, the roads in Tuscany are very well maintained and paved all around, even in the Tuscan countryside. This means getting around Tuscany by car is hugely uncomplicated and doable by anyone who knows how to confidently drive.

Since Florence is the recommended starting point, it’s also the most appropriate location for picking up a rental car. It’s unquestionably the largest city in the area and will have the most options in terms of vehicle choices and availability.

Navigating the well-kept roads of Tuscany can be done with the cheapest rental car you can find (by all means, splurge if you can and want to!).

As long as you know how to drive a manual transmission, it’s sufficient enough to reserve a compact vehicle without AWD/4WD capability and GPS.

You can easily find a rental car for your one week Tuscan road trip for €200 – €300. That’s a small expense for all the amazing places you’ll be able to see by travelling with a car.

Tips for Driving in Tuscany

Heading off on an Italy road trip also means you have to actually drive in Italy. For some, the entire reason one puts off a road trip abroad is the fear of driving in a foreign country, let alone Italy.

We will admit, there is some slight truth to how beautifully chaotic driving in Italy can be. However, we’re here to assure you that you will not find it difficult to drive in Tuscany.

The style of driving in Tuscany is much more slow paced and orderly when compared to Naples or Sicily. Still, there is one or two things you can be mindful of in order to feel fully prepared.

Take it Slow on Country Roads

The Tuscan countryside is first and foremost, land of farming and cultivating. Expect to share the road with tractors and possible herds of animals. Furthermore, you’ll likely remain on the country roads opposed to major motorways which are naturally less scenic.

Although back roads are much more delightful for road trips, they’re also less straightforward. Do not be surprised by the amount of twists and turns you’ll encounter during your Tuscan road trip.

When in doubt, drive slowly and do not mind the cars passing you.

Honking is Normal

The one thing that can easily come as a shock to people driving in Italy for the first time is the amount of honking. Unlike in the U.S., honking usually does not have a negative implication in Italy.

Many times, honking in Italy is a way people merely greet each other or simply let another car or person know “Hey, I’m here!” Do not let the amount of honking deter you from staying focused while driving, it’s just normal business in Italy!

Parking Gets Creative

Luckily, many of the attractions you’ll visit during your Tuscan road trip have designated parking areas. Worried about driving through medieval hilltop towns? Don’t be! Most don’t even allow driving within the town centre unless you live there.

Old and petite villages will have at least one large visitor parking lot at the bottom of the hill instead. This minimises your need to steer through tight streets and nearly impossible parking spots.

Some useful things to know about parking in Italy include:

• To find parking, look for parcheggio in Google Maps or on road signs.
• As a general rule of thumb, blue lines = paid parking and white lines = free parking.
• Fermata describes a brief period of double parking or pulling over for a quick task. It’s widely accepted in Italy and OK to do if you need to park for a few minutes but not permanently.
• No stopping and no parking signs should always be adhered to. They have a blue background with a red “x” or dash through them.

What to Pack for a Tuscan Road Trip

Sun Hat – To keep you protected from the Tuscan sun while effortlessly accessorising.

Travel Adapter – Not just a standard EU adapter but one specifically for Italy’s 20+ outlet types.

Italian Phrase Book – Many people in lesser known destinations in Tuscany do not speak English so learning a few Italian phrases goes a long way!

Road Trip Friendly Laundry Detergent – You may not always have access to a washing machine so have a backup plan.

Packing Cubes – Don’t waste space in your rental car with a ton of luggage. Pack smart with cubes and minimise baggage.

Collapsible Water Bottle – Eliminate waste and save some cash as water in restaurants is not free in Italy. Fill up your reusable water bottle when you can.

Versatile Crossbody Bag – To keep you organized (yet classically stylish) while driving your way through Tuscany.

Related Travel Posts:

• Cutest Small Towns in Tuscany
• Key Tips for Driving in Europe
• How to Master Driving in Puglia
• A Guide on Driving From Italy to Turkey
• Taking a Ferry From Rome to Barcelona
• Puglia Road Trip Guide

Tuscan Road Trip Travel Resources

☔️ TRAVEL INSURANCE: EKTA or VisitorsCoverage

✈️ FLIGHTS: Skyscanner, CheapOair or Kiwi.com

🚙 CAR RENTALS: Discover Cars or Rentalcars.com

🚊 TRAINS & BUSES: Busbud, Trainline or Omio

🛳 FERRIES: Direct Ferries

🛌 ACCOMMODATION: Booking.com, Agoda or Trivago

☎️ ESIM / CELL PHONE DATA: Airalo

📸 TOURS & ACTIVITIES: GetYourGuide or Viator