Tuscany Road Trip: Our Route to the Highlights

Our Tuscany Route on a Map

We’ve mapped out our entire Tuscany road trip route so you can see exactly how to get to all the highlights in Tuscany. It makes planning your Tuscany trip so much easier.

Planning Your Tuscany Road Trip

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

Tuscany is roughly a quarter the size of Bavaria — so not huge, but the highlights are scattered in every direction.

To see the most important ones without rushing, you’ll want to set aside at least 10 days.

You could do it faster, but we planned this itinerary so you actually have time to wander and soak things in — not sprint from one sight to the next.

Best Time to Visit for a Tuscany Road Trip

The best time for a Tuscany road trip is between May and September.

That said, try to avoid the weeks between mid-July and mid-August if you can.

Temperatures can easily hit 35–40°C (95–104°F), which makes sightseeing and driving pretty exhausting.

The absolute sweet spot is late August through mid-September — it’s still pleasantly warm, the days are long, and most of the summer crowds have already headed home.

Don't Drive a Large Car

You’ll spend a lot of time on country roads, but in the most beautiful towns in Tuscany, an SUV or a large estate car is a real disadvantage.

Both in cities and in smaller villages, the streets are often very narrow — a compact car is so much easier to navigate.

The best way to find a good deal on a rental is to compare prices on Discovercars:

Compare rental car prices for Tuscany on Discovercars

roadsurfer: Explore Tuscany by Camper

An experienced camper? Then a larger vehicle is absolutely an option. Renting a campervan or motorhome gives you real freedom — you can reach more remote spots, vineyards, and stretches of coastline at your own pace.

Good to know:

• Many historic centers are car-free — park on the outskirts and explore on foot
• The narrow roads require confident driving skills
• Plan ahead for campsites and parking spots — there are plenty of options throughout Tuscany

Our go-to provider is roadsurfer. You’ll find modern campervans in various sizes, flexible rental options, and plenty of pick-up locations — including in Italy.

Use code 22PLACES for 10% off your booking.

Book a campervan with roadsurfer

Book Museum and Attraction Tickets in Advance

Tuscany is one of the most beautiful places in the world, and it’s busy year-round. Lines are everywhere.

To skip them, you should buy tickets online in advance for the most popular museums and attractions.

The table below shows all the Tuscany highlights where it’s worth booking ahead:

Book Accommodation in Advance

As we mentioned, Tuscany is always busy. So it’s best not to leave your road trip planning to the last minute.

If you’re traveling in peak season between June and August, book everything at least two months ahead.

In the shoulder season — September or May — things are usually a bit more affordable. For trips during those months, aim to book accommodation at least one month in advance.

Our Tuscany road trip starts and ends in Pisa. Let’s go!

Days 0–2: Pisa and Lucca

Day 0: Arriving in Tuscany

The most convenient flights into Tuscany typically land in Pisa, in the north of the region.

You can also fly into Bologna or Florence — you’ll just need to adjust the route slightly.

Option 1: Arriving in Pisa

If you land early in the day in Pisa, you can check into your hotel and then take a first stroll to the Piazza dei Miracoli, where the Leaning Tower stands.

Pisa is not a big city, and the historic center is very manageable.

There are also lots of lovely trattorias around the Piazza — perfect for your first dinner of the trip.

Our hotel picks in Pisa with parking:

You’ll find our full tips for Pisa right here:

Option 2: Arriving in Bologna

Bologna isn’t in Tuscany, but you’re just 1.5 hours from Florence from there.

If you land in Bologna, we’d recommend heading straight to Florence and skipping Pisa and Lucca for now.

If you have enough time, you can always tack those two cities on at the end of the trip. From Volterra — the last stop on our route — it’s about an hour to Pisa.

Or you could spend a day in Bologna first. Our tips for Bologna are here:

Option 3: Arriving in Florence

Direct flights to Florence are available from a number of European hubs — if you’re flying in from elsewhere in Europe, check connections via Munich or Frankfurt.

If you land directly in Florence, make sure to book a hotel with parking — you won’t need the car in the city itself.

The historic center is mostly car-free and completely walkable.

That said, it’s worth picking up your rental car at the airport on arrival, since you’ll be driving out of Florence at the end of Day 2.

More tips on hotels with parking are in the Florence section below.

Day 1: Exploring Pisa

We spend Day 1 in Pisa, taking in the highlights.

The Leaning Tower of Pisa

Everyone who comes to Pisa wants to see the Leaning Tower — that’s a given.

It stands on the Piazza dei Miracoli — “Square of Miracles” — and is actually the bell tower of the cathedral.

The tower leans at four degrees, and while it looks dramatic from the outside, it’s stable and fully secured. You can also go inside and climb up to the 8th floor.

You can buy tickets on-site, but we strongly recommend booking online in advance to skip the line.

Book priority-access tickets for the Leaning Tower of Pisa

Pisa Cathedral

The Cathedral of Santa Maria Assunta stands right next to the Leaning Tower.

This white Romanesque cathedral sits on a sweeping lawn and is free to enter.

If you want to go inside, make sure you’re dressed appropriately — covered shoulders and knees are required.

The Baptistery

Pisa’s Baptistery is a freestanding baptismal church attached to the cathedral — and it’s also the largest baptistery in Christendom.

The building stands 54 meters tall with a circumference of 107 meters. Inside you’ll find a huge baptismal font, a marble pulpit, and numerous marble statues and reliefs.

One of its most special features is its remarkable echo. Every 30 minutes, a guard sings a few notes that combine into a genuinely spectacular sound experience.

The Camposanto Monumentale

The Camposanto is a vast, monumental cemetery behind Pisa’s cathedral.

The whole complex is incredibly impressive — frescoes, late-antique sarcophagi, and a long cloister.

It’s wonderfully quiet and a great escape from the bustle of the Piazza dei Miracoli.

For the Baptistery, the Camposanto Monumentale, and the equally worthwhile Museo Sinopie, there’s a combination ticket you can buy online for 15 euros in advance.

Book the combo ticket for the Baptistery and Camposanto Monumentale

Possible Stops Along the Way

Seeing all these sights will easily fill your whole morning.

Spend the afternoon enjoying a good meal and a leisurely stroll through the old town.

• Eat: Ristoro Pecorino (simple trattoria), L’Ostellino (sandwich shop), Ristorante Cantina Vasari (stylish restaurant)
• Shopping: Borgo Stretto and Via Oberdan (Pisa’s main shopping streets)

Day 2: Arriving in Lucca and Exploring the Old Town

On the morning of Day 2, you check out of your Pisa hotel and head to Lucca.

This medieval town is just 20 kilometers from Pisa, on the road toward Florence.

The City Walls

Lucca’s city walls are among the most significant in Europe — because they’re completely intact.

We’re talking about a four-kilometer structure that fully encircles the historic center.

Today, you can walk along the top, since the walls have been transformed into a beautiful green promenade.

Up there you’ll find lawns, park benches, cafés, and a wonderful view over Lucca and the nearby hills.

Cathedral of San Michele

The Cathedral of San Michele isn’t Lucca’s most historically significant church, but it’s definitely the most beautiful.

It stands on the piazza of the same name, which was once the Forum Romanum — the political and social heart of Lucca in Roman times.

Today the square is lively and welcoming, with several cafés, restaurants, and street musicians. You can pop into the church anytime — entry is free.

Torre Guinigi

This roughly 44-meter tower is one of Lucca’s most iconic landmarks, dating back to the 14th century.

230 steps take you to the top, where you’ll find a small hanging garden with seven holm oaks growing out of it.

No one knows exactly when the trees were planted, but there’s a 15th-century painting that already shows them there.

Piazza Anfiteatro

The Piazza Anfiteatro was originally a Roman amphitheater. You can still tell — the piazza forms a perfect ellipse, with medieval buildings lining its curved edges.

It has exactly four entrances, which were originally the arena’s access points. Today it’s a wonderfully peaceful and well-kept square, with a few cafés and restaurants where you can take a break.

Here are our full tips for Lucca:

Possible Stops Along the Way

By the time you’ve seen everything on Day 2, it’ll probably be around midday. Here are some good spots to take a break in Lucca.

• Eat: Ristorante L’Angolo Tondo (local restaurant on the Piazza dell’Anfiteatro), Antica Locanda dell’Angelo (slightly more upscale), Pizzeria da Felice (seriously good pizza by the slice)
• Shopping: Via Fillungo (Lucca’s main shopping street)

Driving on to Florence

Take the A11 motorway and you’ll be in Florence in about an hour.

Once there, check into your hotel for two nights. For useful hotel tips in Florence, see our dedicated article:

Our hotel recommendations for Florence

Our tip: It’s really worth choosing a hotel with its own parking. Many hotels charge 25 to 30 euros per day for parking, but some offer cheaper or even free spots.
Our hotel picks in Florence with parking:

Days 3–4: Florence

Day 3: Florence's Historic Center

You’ll need at least two full days for Florence.

This Renaissance city is packed with must-sees you really don’t want to rush.

For even more helpful tips on Florence, also read:

The Cathedral of Santa Maria del Fiore

The Florence Cathedral is one of the city’s most iconic landmarks and absolutely impossible to miss.

Its dome was once the largest in the world — today the cathedral is the fourth-largest church in Europe.

Right next to it stands the Giotto Tower, the freestanding bell tower at around 85 meters tall. Entry to the cathedral itself is free and absolutely worth it.

Climbing up to the dome is a must — the view from the top is seriously impressive. But you really need to book tickets in advance; they sell out weeks ahead on the official site:

Book tickets to climb the dome

Possible Stops Along the Way

Before moving on, it’s worth taking a break. On the way to the Piazza della Signoria and the Uffizi, you’ll pass through the lively shopping street Via dei Calzaiuoli.

The area has plenty of restaurants and shops. A good meal before the Uffizi is a smart move — you’ll want at least two to three hours there.

• Eat: O’Vesuvio (one of the best pizzerias in Florence), Osteria del Porcellino (small restaurant with local cooking), I Fratellini (sandwiches to go)
• Shopping: Mercato del Porcellino (daily leather goods market), Mercato di San Lorenzo (daily market for souvenirs, clothes, and leather goods), Via Tornabuoni (luxury fashion boutiques — Gucci, Versace & more)

Piazza della Signoria

From the cathedral, the busy shopping street Via dei Calzaiuoli leads you straight to the Piazza della Signoria — Florence’s main civic square.

It sits right in front of the fortress-like city hall, the Palazzo Vecchio, which was once the residence of the powerful Medici family.

Also on the piazza is the Loggia dei Lanzi, a Gothic arcade filled with important sculptures. These are copies, though — the originals are all in the various museums of Florence.

The Uffizi Gallery

Right next to the Piazza della Signoria and the Palazzo Vecchio, you’ll find the Uffizi Gallery.

This is one of the world’s greatest art museums, housing works from antiquity through the late Baroque. Among the highlights: paintings by Leonardo da Vinci, Michelangelo, and Sandro Botticelli’s “Birth of Venus”.

Set aside at least two hours for the Uffizi. Book your tickets in advance — the line at the door is always long.

Timed entry to the Uffizi costs 29 euros per person.

Book priority-access tickets for the Uffizi Gallery

You can also visit the Uffizi with a guided tour, which is a great option if you’re short on time — the guide takes you straight to the most important works.

Book a guided Uffizi tour with priority access

Ponte Vecchio

The Ponte Vecchio is just a few minutes’ walk from the Uffizi — its name simply means “Old Bridge.”

It’s a fully built-up bridge, with dozens of jewelry shops lining its little houses. And it’s been that way for around 500 years.

In the middle there’s a small open section where street musicians play daily and you can look out over the river.

Piazza Santa Croce

From the Ponte Vecchio, you can walk upstream along the river, past the Uffizi toward the Ponte alle Grazie bridge.

From there, turn left onto Via de’ Benci — a street that really comes alive in the evenings — which leads you straight to Piazza Santa Croce and its famous church.

The church is worth visiting not just for its Romanesque architecture, but because inside you’ll find the tombs of some of history’s greatest minds: Galileo Galilei, Michelangelo, and Machiavelli are all buried here.

It’s never too crowded, so tickets can easily be bought on the spot. Admission is 8 euros per person.

Day 4: The Gardens and Viewpoints of Florence

On your second day in Florence, you’ll explore the highlights on the other side of the Arno.

It’s worth taking the car for this, so you can drive straight on to the Chianti region at the end of the day without heading back to the hotel.

A convenient parking garage on the south bank is the Parcheggio Oltrarno, where you can park for 2 euros per hour.

Palazzo Pitti

The Palazzo Pitti is about a ten-minute walk from the Parcheggio Oltrarno.

It’s a massive Renaissance palace from the 15th century that now houses several museums.

These include the Medici family’s painting collection, the Royal Apartments, the Gallery of Modern Art, the Costume Museum, and the Carriage Museum.

Tickets for the Palazzo Pitti cost 16 euros on the door, giving you access to all the exhibitions.

The line at the entrance is always long, though, so it’s worth buying tickets online in advance.

Book skip-the-line tickets for Palazzo Pitti

Possible Stops Along the Way

After the Palazzo Pitti, you’ll probably be ready for lunch. Luckily, this part of Florence has some really lovely small trattorias.

• Eat: Trattoria La Casalinga (classic Florentine cooking), Osteria dell’Enoteca (excellent wine selection), GustaPizza (seriously good pizza in a lively atmosphere)

Boboli Garden

The Boboli Garden is a vast park belonging to the Palazzo Pitti — though it has a separate entrance and a separate ticket.

Laid out in classic 16th-century Italian style, the garden is full of statues, grottos, and fountains, with shaded gravel paths and wonderful views over Florence.

There are no bars or cafés inside, so it’s worth bringing a water bottle and a snack.

A ticket for the Boboli Garden costs 10 euros per person and includes the Museum of Silverware inside the grounds.

Piazzale Michelangelo

From the Oltrarno parking garage, you’re just five minutes’ drive from one of the best vantage points in Florence: the Piazzale Michelangelo.

The drive takes you uphill through a beautiful villa district, past parks and grand gateways, all the way to the piazzale.

Parking at Piazzale Michelangelo is free. And the panorama over Florence from up here is simply the best in the city.

Especially in the late afternoon and at sunset, the view is just stunning.

San Miniato Al Monte

From Piazzale Michelangelo, it’s just a short walk to Florence’s highest church: San Miniato Al Monte.

Thanks to its dramatic position high above the city, it’s considered one of the most beautiful churches in Italy.

A steep, wide staircase leads up to the church terrace. From the top, the view over Florence is almost even more impressive than from Piazzale Michelangelo.

Note that you can only go up until 7 PM — after that, the gate at the bottom closes.

With that, you’ve seen all the major highlights of Florence and can head straight on.

Driving to Your Chianti Accommodation

As a base for the next few days, we recommend booking a stay at an agriturismo — a working farm or vineyard — in the Chianti region.

Chianti is perfectly positioned for day trips to all the destinations coming up.

Beautiful vineyard stays in Chianti:

Days 5–6: San Gimignano and Siena

Day 5: The Old Town of San Gimignano

In the heart of Tuscany, San Gimignano is one of the most remarkable small towns on any itinerary. Half a day is plenty — it’s very compact.

We deliberately kept Day 5 to a half-day, because by this point you’ll probably also want some time to relax by the pool at your agriturismo.

Piazza del Duomo

Walk through one of San Gimignano’s stone town gates, follow the lanes inward, and you’ll soon arrive at the Piazza del Duomo.

The square is paved with red bricks and completely surrounded by medieval towers and buildings.

Along with cafés and boutiques, you’ll find San Gimignano’s cathedral, the town hall, and the Torre Grossa here.

The tower stands 54 meters tall — the highest of all San Gimignano’s towers.

Torre Grossa

The Torre Grossa is the only tower in San Gimignano you can actually climb.

The ascent involves 280 steps, which isn’t exactly easy, but the stairs are wide and made of metal.

Only right at the very top does it get a bit tight — you climb through a kind of hatch onto the viewing platform.

On the way up, there are multimedia screens explaining the history of the tower and the town.

The climb is totally worth it — from the top you get a sweeping panorama over San Gimignano and the entire Tuscan landscape.

Piazza della Cisterna

Right next to the Piazza del Duomo is the Piazza della Cisterna.

This is probably San Gimignano’s most beautiful square, centered around an octagonal well.

Like the other piazza, it’s completely surrounded by medieval towers and buildings, and lined with small trattorias and shops.

It’s also home to one of the best gelaterias in the world: Gelateria Dondoli, which has won multiple World Gelato Championships.

It’s well-known — so yes, there will be a line. But it’s absolutely worth joining. So, so good!

Rocca di Montestaffoli

To the left of the cathedral, a small street leads uphill to the castle ruins of Montestaffoli.

Not much remains of the original fortress — just a tower and the outer walls.

But the walk up is still worth it, because inside the walls there’s a small park where you can sit in the shade of cypress trees.

You also get a wonderful panoramic view over the surrounding countryside from up here.

Possible Stops Along the Way

• Eat: La Mandragola (great terrace with views), Le Vecchie Mura (good value, also with a terrace)
• Views: Walk along Via Piandornella for sweeping views over the landscape

Our full tips for San Gimignano are here:

Day 6: Exploring Siena

You’ll want a full day for Siena.

The historic center is mostly traffic-free, but there are several parking garages nearby — for example the Parcheggio Il Campo and the Parcheggio Il Duomo.

Both charge a day rate of 35 euros, or 2 euros per hour.

Piazza del Campo

The vast Piazza del Campo is surrounded by several significant palaces, including the Palazzo Pubblico (the city hall) and the Cappella di Piazza.

On the upper side of the piazza stands a monumental fountain, the Fonte Gaia — which translates roughly as “Fountain of Joy.”

The name comes from 1342, when the architect first managed to bring water into the city through a 25-kilometer-long aqueduct — a cause for celebration at the time.

The Piazza del Campo is the heart of Siena. It hosts events like the centuries-old Palio di Siena horse race, and is lined with restaurants and cafés.

Torre del Mangia

The Torre del Mangia is Siena’s most iconic landmark — the bell tower of the Palazzo Pubblico.

It stands right on the Piazza del Campo and at 88 meters is the tallest tower in the city.

The bell isn’t perfectly cast, giving it a slightly off-key sound.

You can climb the tower — it’s over 400 steps to the top. But it’s really worth it; the view is superb!

Siena Cathedral

Siena Cathedral sits on a hill above the historic center and is one of Italy’s most celebrated churches.

It’s genuinely impressive both inside and out. Inside, you’ll also find the Piccolomini Library, with frescoes by Raphael and Michelangelo.

The cathedral complex also includes an unfinished section with a viewing platform.

Book your tickets in advance — it’s absolutely worth it:

Book tickets for Siena Cathedral

Possible Stops Along the Way

• Eat: La Taverna di San Giuseppe (excellent home-style cooking), Prètto Prosciutteria (great value, really tasty)

Days 7–8: Cortona and Val d'Orcia

Day 7: Exploring the Hill Town of Cortona

Cortona is a must on any Tuscany road trip. The town sits in the far east of the region and is reachable from Siena in about an hour.

Built into a hillside, Cortona is worth visiting not only for its medieval architecture but also for the incredible views you get from up there.

Plan for at least half a day.

Piazza della Repubblica

This is Cortona’s most famous square and has served as a backdrop for various films (including “Under the Tuscan Sun”).

The square is home to several important buildings, including the Palazzo Comunale with its wide staircase and the Palazzo Passerini.

You’ll also find several small restaurants, boutiques, and cafés on the square.

Museo dell'Accademia Etrusca

Just a few steps from the Piazza della Repubblica is the Piazza Signorelli, home to the important Museum of Etruscan Art.

The Etruscans were the original people of Tuscany and founded many of its cities long before the Romans.

Cortona was one of those cities, which is why it holds such a significant collection of Etruscan artifacts.

Piazza del Duomo

Cortona also has a cathedral, just 500 meters from the Museo dell’Accademia Etrusca.

It stands on the foundations of an Etruscan temple.

Entry is free — just make sure you’re dressed appropriately.

One wall of the cathedral sits right at the edge of the hillside, so from the cathedral square you get a wonderful view over the Val di Chiana valley below.

Possible Stops Along the Way

• Eat: Ristorante Il Cacciatore (affordable Tuscan cooking), Umami (sushi with an outdoor terrace)
• Shopping: Via Nazionale (lots of artisan boutiques)
• Views: Piazza Garibaldi

Day 8: Val d'Orcia

Set aside a full day for a drive through the Val d’Orcia.

We’d suggest visiting the towns in the morning and early afternoon, then saving the late afternoon for landscape photography.

The colors of the Val d’Orcia at that time of day are just spectacular.

Montalcino

If you’re approaching the Val d’Orcia from the north, Montalcino is the first stop.

With just under 6,000 residents, Montalcino punches well above its weight in terms of things to see. It’s also the home of the world-famous red wine Brunello di Montalcino.

The town is encircled by a city wall with six gates and is perfect for exploring on foot.

The main draws include the cathedral, the walls themselves, the Piazza del Popolo, and the medieval fortress that dominates the hilltop.

The fortress can be explored fully — and it’s absolutely worth it. From the watchtowers you get a breathtaking view over the entire Val d’Orcia.

Pienza

Like Montalcino, Pienza is a popular village in the Val d’Orcia. It also sits on a hilltop and offers lovely views over the valley.

The entire village is a UNESCO World Heritage Site.

There’s a cathedral, the old town hall (Palazzo Comunale), well-kept medieval lanes, and wide terraces with great views over the surrounding hills.

Cappella della Madonna di Vitaleta

This tiny chapel is one of Tuscany’s most iconic postcard images.

It’s a small chapel standing between two rows of cypress trees in the middle of a field.

On the SR146 road between Pienza and San Quirico d’Orcia, there’s a spot where tour buses and cars park daily so travelers and photographers can capture the chapel.

Even if it’s often crowded, the stop is worth it to get your own shot.

Days 9–10: Saturnia, Pitigliano, and the Journey Home

Day 9: The Hot Springs of Saturnia and the Etruscan Town of Pitigliano

Day 9 — the second-to-last day of your road trip — is dedicated to the deep south of Tuscany.

Down here there are no cities, just villages and natural highlights.

One of the most beautiful spots in southern Tuscany is Pitigliano.

Among the best-known natural attractions are the hot springs of Saturnia.

Pitigliano

Plan for a morning or afternoon in Pitigliano.

It’s one of the few places in Tuscany that isn’t completely overrun — but it’s well worth the visit, if only for its extraordinary appearance.

The town perches on a pedestal of tufa rock, high above the surrounding forests.

Pitigliano was founded by the Etruscans, though accounts suggest people settled here as far back as the Bronze Age — around 10,000 years ago.

The highlights include a 17th-century aqueduct, the Palazzo Orsini (once the seat of the powerful Orsini family), the cathedral, and the Jewish quarter.

In the Jewish quarter you’ll find a synagogue, a kosher slaughterhouse, and a kosher wine cellar.

The Palazzo Orsini also houses an archaeological museum dedicated to Etruscan art.

The Hot Springs of Saturnia

In the late afternoon, make your way to the hot springs of Saturnia — just half an hour’s drive from Pitigliano.

Here, water at 37°C (99°F) bubbles up from the rock and flows into several naturally formed pools where you can soak and unwind.

A dip is absolutely worth it and makes for a wonderful end to your Tuscany road trip! The pools are free to access and great fun if you’re traveling with kids too.

Day 10: The Journey Home via Volterra

If your flight home isn’t until the afternoon or evening, you might have time on Day 10 for a short detour through Volterra.

From the Siena area, take the SR68 country road toward the coast. On the way, you’ll pass through the Etruscan city of Volterra — another really worthwhile stop in Tuscany.

Volterra has a 3,000-year history and is considered Italy’s capital of alabaster craftsmanship. The entire historic center is full of small artisan boutiques where you can pick up alabaster souvenirs.

From Volterra, continue toward Cecina on the coast, then take the coastal road SS1 north toward Pisa — a lovely drive with great sea views along the way.

Extra Tip: Beach Time on Elba

If you have a few extra days, why not add a beach break to your Tuscany road trip? We’d recommend the island of Elba, which has some of the most beautiful beaches in Tuscany.

Elba is also part of Tuscany and sits about 10 kilometers off the Tuscan coast.

To get there, head to the port town of Piombino — about two hours by car from Siena.

From Piombino, car ferries run several times per hour to Elba, with the crossing taking one hour.

The journey is well worth it: Elba is one of the most beautiful islands in the Mediterranean and the beaches are simply stunning.

Crystal-clear water, a colorful underwater world, and a great range of places to stay across the whole island. Check out our articles on Elba: