Tuscany itinerary: Things to do in Tuscany on a 5-7 day roadtrip (+ map)

Toskánsko itinerář: 5-7 denní roadtrip po Toskánsku (+ mapa)

Join us on a roadtrip through Tuscany and discover a region with green hills, vineyards, charming villages and Renaissance towns. We’ve designed this five to seven-day itinerary to help you discover the most beautiful places to go in Tuscany.

There are so many great things to do in Tuscany that it’s almost impossible to include everything in one itinerary. In this article, we will show you several options depending on how much time you plan to spend in Tuscany. If you’ve already been to Tuscany, this article with the most beautiful places in Tuscany will help you find more inspiration on what to visit in one of the most beautiful regions in the world.

How to plan a 5-7 day itinerary in Tuscany

In this article we will show you three sample itineraries on how you can approach a visit to Tuscany. The first itinerary focuses on the best things to see in Tuscany – from breathtaking Florence and Siena, to the beautiful countryside of Val d’Orcia, to the medieval villages and thermal springs of Saturnia.

Tuscany is vast and it takes a long time to get from north to south. The next itinerary is therefore focused only on northern Tuscany, stretching between Florence, Pisa and Siena. In the third itinerary, on the other hand, we will get acquainted with southern Tuscany.

The itineraries can be customised to your liking – each day you have a choice of how you can spend your day. The aim is to give you an idea of where things are, what you can visit in the area and choose the places that interest you accordingly.

How to protect yourself when travelling by car: Auto insurance provides you with car insurance to get your car repaired, towed to a garage, transported back home or a replacement vehicle if needed.

Itinerary of things to do in Tuscany on map

HOW TO USE THIS MAP: Above you will find a map of the roadtrip in Tuscany, Italy. Click at the top left of the map to see separate layers with highlighted locations. You can hide and show the different layers or click on the icons on the map to see the names of the places mentioned in the itinerary for Tuscany. If you want to save the map, star it. For a larger version, click on the icon in the upper right corner.

ITINERARY 1: THE BEST OF TUSCANY

7 DAY ROADTRIP IN TUSCANY

  • Day 1: Florence
  • Day 2: Lucca and Pisa
  • Day 3: San Gimignano and SentierElsa
  • Day 4: Siena and Monteriggioni
  • Day 5: Val d’Orcia – Pienza – Montepulciano
  • Day 6: Saturnia and Pitigliano
  • Day 7: Seaside Tuscany

Day 1: Florence

Florence is the capital of Tuscany and one of the most beautiful cities in Europe. Charming, elegant, full of history, art and spectacular views.

Start your visit early in the morning at the Cathedral of Santa Maria del Fiore, when it’s the best time to climb the dome for a view of the city (advance booking required – they tend to sell out weeks in advance).

santa maria del fiore florence / what to see in florence

Then wander the narrow streets that wind in all directions, visit the medieval Piazza della Signoria and cross the unusual Ponte Vecchio bridge. Head to Santo Spirito to the right of the bridge and enjoy the authentic atmosphere. For the best sunset views, head to the Bardini Gardens (pay) or Piazzale Michelangelo (free).

florence in 2 days

☞ More information in our 2-day itinerary for visiting Florence. Even though the itinerary is for 2 days, it will give you a basic overview of best things to do in Florence, where to eat or where to go for the best gelato.

Where to stay in Florence

If you are travelling by public transport, the best accommodation is near Santa Maria Novella Station or in the centre, which is just a few minutes’ walk from the station.

When travelling by car, choose accommodation outside the centre, where access is restricted (ZTL zone).

Accommodation Florence 😴

ubytování florencie
hu Firenze Camping in Town

Bungalows with private bathroom and parking

ubytování florencie
Art Hotel Museo

Modern 4* hotel with swimming pool near Florence

Day 2: Lucca and Pisa

Lucca (things to do in Tuscany)

The next day we start in Lucca. If Tuscany has a hidden gem, it is Lucca. The city has a similar atmosphere to Bologna, for example – lively, authentic and well visited by Italians.

Lucca Tuscany

Take a walk along the well-preserved walls or climb the Torre Guinigi, unique for its trees at the top. Enjoy a stroll through the winding streets that lead you to the magnificent Piazza dell’Anfiteatro or the imposing cathedral.

Lucca has a number of excellent trattorias serving Tuscan cuisine. If you’re looking for a good handheld pizza, try Dante & Gentucca.

Lucca, Tuscany
View from the Guinigi Tower

Pisa

Enjoy most of the day in Lucca and later in the afternoon transfer to Pisa. It is only half an hour by car or train.

We think Lucca has a more beautiful historic centre, so we would recommend spending just a few hours in Pisa towards the end of the day. Plus, by this time the biggest crowds will be gone.

Pisa Italy Tuscany / Piazza dei Miracoli / Piazza dei Miracoli

Pisa is dominated by the Piazza del Duomo, a magnificent complex with an ornate leaning tower, a breathtaking cathedral, a baptistery and a cemetery. The setting sun bathes the sights in golden hues and you can enjoy the view from the tower and a visit to the cathedral with its ornate font. All sights are open until 20:00, so you have plenty of time to visit them.

☞ We wrote a separate guide to what to see in Pisa. It also includes a map, detailed information on sightseeing and restaurant tips.

Alternative: If you’re arriving in Pisa and renting a car locally, swap the first two days of this itinerary – visit Pisa and Lucca first before moving on to Florence.

Day 3: San Gimignano and SentierElsa

We have had two busy days in Tuscany. The third day will therefore be more relaxed. Preferably by the pool at the Tuscan villa, where you can enjoy delicious local cuisine.

SentierElsa

Fancy a walk in the beautiful countryside? Take the Elsa Trail, located between San Gimignano and Siena. The route is 2 km long in one direction and leads through the forest around the river with its beautiful turquoise water and the Diborrato waterfall.

sentier elsa tuscany roadtrip

Don’t forget your swimsuit (and water shoes) so you can cool off along the way. Due to the easy nature of the route, it is often crowded during the season, especially on weekends.

Tip: If you plan to rent a car, I recommend booking well in advance to ensure you get the best price and choice. In addition, Tuscany is very popular and last-minute availability can be very limited.

San Gimignano – things to do in Tuscany

Enjoy an early evening in San Gimignano, a beautiful UNESCO World Heritage Site. It is nicknamed “Tuscan Manhattan” because there are 14 towers that are visible from a distance.

Climb over 200 steps to the Torre Grossa tower and enjoy fantastic views of the city. Wander the streets around Piazza del Duomo and Piazza della Cisterna, home to Gelateria Dondoli, voted the best gelateria in the world.

View of San Gimignano from Torre Grosso
View of San Gimignano from Torre Grosso

San Gimignano is usually crowded in high season. Later in the afternoon the biggest crowds will be gone and it will be pleasantly quiet for the evening. Enjoy its peaceful atmosphere and stroll through the charming medieval streets. You can watch the sunset from Parco della Rocca, where there is a viewpoint, seating area and children’s playground.

San Gimignano Tuscany

Note: The centre of San Gimignano is not accessible by car. There are several paid car parks in the area – car park P1 is 15 minutes from the historic centre (uphill) and is therefore the cheapest. The P3 car park is more expensive, but on the other hand it is connected to the centre by a lift.

Where to stay in Tuscany

The accommodations below provide the perfect base for exploring Tuscany. Surrounded by greenery, with excellent cuisine and friendly staff. There is also a swimming pool where you can cool off on warm days.

Accommodation in Tuscany 😴

ubytování toskánsko
Villa Casa di Campagna

Wonderful accommodation with swimming pool

ubytování toskánsko
Villa Gloria

Cosy hotel in the middle of the vineyards

Day 4: Siena and Monteriggioni

If you ask a local what not to miss in Tuscany, most will tell you Siena. Siena is a beautiful city with a lot to see. You can easily spend 2 full days here, but even in a few hours you can walk through its beautiful centre.

Siena, like Pisa and Florence, is also very touristy, so I would recommend starting as early in the morning as possible. Park in this car park (payable approx. 2 €/hour) and take the covered escalator (free of charge) to the historic centre.

Siena Tuscany

Within moments, you’ll be over the hill and at the Duomo di Siena. The cathedral doesn’t open until 10:30am, so you can stop here on your way back to the car park. The Duomo is famous for its ivory marble façade and richly decorated interior, including a floor with inlaid marble that tells biblical stories.

Siena Tuscany - the most beautiful cities in Tuscany

Just a few steps from the Duomo is Piazza del Campo, the famous medieval shell-shaped square. The best view of the Wall can be had from here or from the fortress a little higher up.

Where to stay in Siena

Siena provides full city facilities – there are plenty of restaurants and shops. On the edge of the centre outside the ZTL zone there are plenty of hotels with parking, from where you can easily reach the sights. In addition, some of the hotels offer a magnificent view of the old town.

Accommodation Tuscany 😴

ubytování siena toskánsko
Hotel Minerva – Siena

Cosy hotel with a wonderful view and parking

ubytování siena toskánsko
Hotel Moderno – Siena

Pleasant hotel in a medium price range

Monteriggioni

If you still have the time and inclination to explore other charming towns, Monteriggioni is close to Siena.

Monteriggioni, a medieval hilltop village, is famous for its imposing walls and watchtowers that form a perfect panorama. Take a walk around the walls and enjoy the medieval atmosphere of the village.

A large paid parking lot is located below the village. From here, it’s just a few minutes before you reach the gates of Monteriggioni. You will only need 1-2 hours for your visit.

Alternative: If you’re pressed for time, combine a visit to San Gimignano and Siena into one day and skip SentierElsa and Monteriggioni.

Day 5: Val d’Orcia – Pienza – Montepulciano

Do you want to experience the real Tuscany, which has been the model for many famous painters? The Val d’Orcia is located between Montalcino and Montepulciano and has been a UNESCO World Heritage Site since 2004. If you’re staying in the Siena area, it takes about an hour by car.

The rolling hills of the Val d’Orcia are covered in vibrant vineyards, golden wheat fields and iconic cypress trees, creating a postcard-perfect setting. Here you can taste some of Italy’s finest wines, including the famous Brunello di Montalcino and Vino Nobile di Montepulciano.

Monticchiello, Tuscany
Monticchiello, Tuscany

It’s places like this in Tuscany that make it better to have your own car or rent one locally. Just drive through the valley and you will come across a series of turns that lead past vineyards to viewpoints, chapels and Tuscan villas. There is usually an area to park at places of interest.

Pienza

Pienza, a beautiful town in the Val d’Orcia, completely captivated us with its UNESCO-listed historic centre. Moreover, it is the “ideal city of the Renaissance”, designed by Pope Pius II. as a model of harmonious urbanism.

During your visit, don’t miss a taste of the local pecorino cheese and a walk around the town’s fortifications, from which you can enjoy fantastic views of the Val d’Orcia.

Pienza Tuscany Italy

There are hiking trails that run along the vineyards in the shade of cypress trees. The best route is along Campi Elisi, southwest of the town, where several scenes from the film Gladiator were shot.

Pienza is a small town, even with a walk it won’t take you more than 2 hours. There are several paid parking lots around the centre.

If you want to taste the real cuisine of the Piento area, visit this osteria. Cozy atmosphere and delicious food.

Pienza Tuscany Italy

Montepulciano

In the hills among the vineyards of Val d’Orcia lies Montepulciano, a town famous for its beautiful Renaissance architecture and excellent Vino Nobile wine.

Wander the charming streets and discover sights such as the Palazzo Comunale (climb the tower for a spectacular view) and Santa Maria Assunta Cathedral. For another view, I recommend this viewpoint just outside the old town.

On your way to Montepulciano, don’t miss the Church of San Biagio, which is accessible from the centre.

There are several car parks around the town. For the easiest access to the historic centre, park in car park P8. If you are lucky, you will find free parking spaces. Please allow at least 2 hours for your trip to Montepulciano.

Montepulciano Tuscany

Val d’Orcia

You can spend a whole day in Val d’Orcia. Visit several villages, taste wine in one of the wineries or walk among the vineyards. Especially for sunrise or sunset, there’s no mistaking it.

Montefollonico, Monticchiello, Castiglione d’Orcia or San Quirico d’Orcia are also worth a short visit, with far fewer tourists – all the tips are also marked on the map at the beginning of the article. Each of the villages can be walked through in an hour and free parking is usually on the edge of the village.

Accommodation Tuscany 😴

ubytování toskánsko
Certosa di Pontignano Residenza d’Epoca

Wonderful accommodation in a former monastery

ubytování toskánsko
Bosco Della Spina

Infinity pool, Tuscan cuisine, beautiful view

Day 6: Saturnia and Pitigliano

Saturnia

We move to the very south of Tuscany, where we visit the thermal springs of Cascate del Mulino in the small village of Saturnia. These are cascading hot waterfalls formed by thermal springs.

The place is very popular and it’s also free to access, so it’s a good idea to arrive as early in the morning as possible, preferably at sunrise. The perfect calm and the beautiful blue colour of the water elevate the early morning experience even more.

saturnia tuscany

Practical tips: parking is 5 minutes from the springs – turn right on the way to the springs (payable at 2,5 €/hour between 8:00 and 20:00). There are also refreshments and lockers for storing belongings. Take change and water shoes for the pebbles.

How to protect yourself when travelling by car: Auto insurance provides you with car insurance to get your car repaired, towed to a garage, transported back home or a replacement vehicle if needed.

Montemerano

Just a few minutes’ drive from the Saturnia thermal springs is Montemerano, a typical Tuscan hilltop village with stone houses and spectacular views.

The historic centre is really small, perfect for a short stop on the way or for lunch, as there are several local trattorias. Free parking is located a short walk from the entrance gate.

Montemerano Tuscany

Pitigliano (things to do in Tuscany)

Pitigliano is only half an hour’s drive from Saturnia or Montemerano. This is a place not to be missed in the south of Tuscany. Moreover, far fewer tourists head here than to Siena or San Gimignano.

Pitigliano is a breathtaking place, a village built on a volcanic rock that resembles the Temple Mount in Jerusalem. That is why it is nicknamed “Little Jerusalem”.

Pitigliano Tuscany Italy

The road here is already panoramic and offers beautiful views. For an even better view of Pitigliano, enter the coordinates 42.63352011836821, 11.670796846291381. There are a few benches and you can park a little further on in the car park behind the cemetery (paid, but good price).

Pitigliano Tuscany Italy

From the car park you can walk around the viewpoint to the centre in about 10 minutes. Wander the cobbled streets that lead you to small squares and viewpoints with further views of the city and surrounding area.

Pitigliano is not big – it can be walked in 2 hours.

Sorano

An alternative is Sorano, just a few minutes from Pitigliano. A beautiful city from the Etruscan period (like Pitigliano), which they carved into the rock. For this reason, it is nicknamed the “Matera of Tuscany”.

The town itself is definitely worth seeing, with its old streets and houses where a good chunk of history has been written.

Sorano, Tuscany Italy

If you’re here, I recommend taking the Via Cava di San Rocco trail, which offers spectacular views of Sorano and the surrounding countryside. The trail is carved into the tuff, including rock rooms, so you walk among the high rocks.

Rock dwellings along Via Cava di San Rocco Sorano, Italy
Rock dwellings along Via Cava di San Rocco

It’s a nice change after exploring Tuscan villages and towns. The trail is short and not circular, so you have to go back the same way. There are several parking spaces.

Views of Sorano from Via Cava
Views of Sorano from Via Cava

Where to stay near Saturnia and Pitigliano

Near the Saturnia springs there are Agroturismo and hotels, from where you can reach the thermal springs just a short walk away. At the same time, you can easily reach other nearby places such as Pitigliano or Montemerano.

Accommodation South Tuscany 😴

ubytování toskánsko
Agriturismo Le Cascatelle – Saturnia

Excellent cuisine, private beach, parking

ubytování toskánsko
B&B 8380 Saturnia Terme – Saturnia

Good price, parking, quiet environment

Day 7: Seaside Tuscany

After a busy schedule, a rest by the sea will come in handy. Here are a few beaches near southern Tuscany:

Scarlino beaches: 11 km of beaches near the town of Scarlino. To the north is Puntone Beach, ideal for families with children. Further south, you can walk to the free beach of Cala Martina, behind which lies one of the most beautiful beaches in Tuscany, Cala Violina.

beach tuscany

Spiaggia della Feniglia Beach: located near Orbetello, Spiaggia della Feniglia is a long sandy beach surrounded by a lush pine forest. The beach is free, with paid parking a few minutes from the beach.

Castiglione della Pescaia: This popular seaside town is famous for its beautiful beaches, including Spiaggia delle Rocchette and Spiaggia di Cala Violina. The beaches here are characterised by golden sand, clear waters and a wide range of facilities and services.

Livorno

In the north of Tuscany is the seaside resort of Livorno. It’s not as magical as Florence or Siena, but the sunset from here is worth it. You can watch the sun setting over the horizon from the spacious and landscaped promenade of Terrazza Mascagni. There is a small aquarium, paid parking and several restaurants nearby.

Livorno Tuscany - Sunsets on Terrazza Mascagni, Livorno
Sunsets at Terrazza Mascagni, Livorno

ITINERARY 2: NORTH OF TUSCANY

5-7 DAY ROADTRIP IN TUSCANY

  • Day 1: Florence
  • Day 2: Chianti wine region
  • Day 3: Siena
  • Day 4: Monteriggioni and SentierElsa
  • Day 5: San Gimignano and Volterra
  • Day 6: Pisa and Lucca
  • Day 7: Montecatini Terme and Pistoia

Day 1: Florence

Florence is the jewel of Italy. A beautiful city full of Renaissance art, where you can walk for hours and still discover new places. From extensive art collections, medieval streets to fantastic views of the city.

baptistery florence in 2 days
Mosaic in the baptistery of the Santa Maria del Fiore Cathedral complex

You can easily spend two or more days in Florence. It is also a good base for exploring the area if you would like to stay in a larger city where everything is close at hand.

☞ We have already written several articles about Florence – here is 2 day itinerary in Florence or get inspired, what to see in Florence. For more information on transport and how to enjoy the city, see Florence guide.

Recommended accommodation near Florence

  • hu Firenze Camping in Town: Accommodation in bungalows with bathroom and free parking, great price and access to the centre and the north of Tuscany
  • Art Hotel Museo: Modern 4* hotel with swimming pool on the outskirts of Florence, most places within an hour’s drive

Day 2: Chianti wine region

From Florence, take the regional road 222 towards Siena, from which you can enjoy the Tuscan countryside. In general, in Tuscany it is better to choose local and regional roads, which offer better views than the main roads.

Chianti is a famous region known for its picturesque landscape with rounded hills and vineyards where wineries are scattered. Some of Italy’s finest wines are produced here, especially the iconic Chianti Classico.

Chianti Tuscany Italy / what to visit in Tuscany

Visit La Fattoria di Montemaggio, a peaceful winery where owner Francesco will treat you to a visit and show you the wine-making process.

You can also explore medieval villages such as Greve in Chianti and Radda in Chianti and sample local specialities.

If your base is Florence, you can go to an escorted tour of the Chianti vineyards, which also includes visits to Siena, San Gimignano and Pisa. It’s a packed trip, visiting the best of Tuscany.

chianti tuscany itinerary / things to do in tuscany
Vineyards near Radda in Chianti

Day 3: Siena

The next day we visit the jewel of Tuscany, which lies in the heart of the region – Siena is one of the most beautiful cities in Italy.

The centrepiece of Siena is the Piazza del Campo, a beautiful square famous for its shell shape, which also appeared in a Bond film chase. Don’t miss a visit to the Duomo, with its intricate facade and magnificent interior decorated with frescoes and statues. Wander the narrow, winding streets and immerse yourself in the medieval atmosphere of the city.

siena things to do in tuscany itinerary
Piazza del Campo in Siena

All car parks are located on the edge of the centre, from where you have to walk uphill. If you park in this car park, you can take the escalators to the historic centre.

I recommend staying overnight in the city and enjoying the sunrise or sunset, when the warm light hits the red-orange facades of Siena’s houses.

Recommended accommodation in Siena

Day 4: Monteriggioni and SentierElsa

We have had a few busy days, so we will spend the fourth day more quietly.

SentierElsa

Start your day with a walk in the beautiful countryside. Take the Elsa Trail, an easy trail through the woods past a river with beautiful turquoise-coloured water.

sentier elsa tuscany roadtrip

The route is 2 km long in one direction. On the way you can swim – it is better to pack water shoes. Due to the undemanding nature of the route, it is often crowded during the season, especially on weekends.

Monteriggioni

End the day in Monteriggioni, a charming village surrounded by well-preserved medieval fortifications. The tour won’t take you long, but the village has its own charm and is definitely worth seeing if you are in the area.

I recommend taking a walk around the walls (which includes a museum) for a small fee and going to an osteria with outdoor seating for a meal. A perfect end to the day.

monteriggioni things to do in tuscany

A large paid parking lot is located below the village. From here, it’s just a few minutes before you reach the gates of Monteriggioni. You will only need 1-2 hours for your visit.

Alternative: If you’re pressed for time and only have 5 days to visit Tuscany, combine a tour of Chianti with a visit to Siena and skip Monteriggioni and SentierElsa. They are beautiful places, but they are not necessarily among the must-see places in Tuscany.

Accommodation Tuscany 😴

ubytování toskánsko
Relais Santa Chiara Hotel

4* hotel near San Gimignano, swimming pool, excellent food

ubytování toskánsko
Agrihotel Il Palagetto

Excellent cuisine, view of the Volterra, swimming pool with seating

Day 5: San Gimignano and Volterra

San Gimignano

Between Volterra and Siena you will find on a hill the jewel of Tuscany – San Gimignano, a town that is a UNESCO World Heritage Site thanks to its unique historical character.

It is nicknamed the “Tuscan Manhattan” because there are 14 towers that are visible from a distance. In the past there were many more of these towers, because the tower here symbolized power and wealth.

san gimignano tuscany itinerary

At the foot of San Gimignano you will find several paid car parks – P1 is the cheapest (15 minutes walk uphill), P2 is the closest but the most expensive. Equally expensive is P3, from which you can get to the old town by elevator.

Volterra – things to do in Tuscany

In the afternoon we transfer to Volterra, which offers a quieter atmosphere than San Gimignano. A beautiful hilltop town, famous for its ancient Etruscan origins. Here, you can literally breathe in ancient history, which you will absorb in the archaeological park, including the Roman theatre, Etruscan tombs and the Etruscan gate of Porta all’Arco.

Volterra the most beautiful town in Tuscany

Volterra’s medieval character is enhanced by its well-preserved walls, narrow streets and the Cathedral of Santa Maria Assunta with the Baptistery of San Giovanni.

The parking garage is located near the historic center.

Book your car in advance to ensure the best price and choice. Plus, Tuscany is very popular and last minute offers can be very limited.

Volterra the most beautiful town in Tuscany

Day 6: Pisa and Lucca

Pisa

Start your day in Pisa at Piazza del Duomo. Here you’ll find a complex of buildings with ornate facades and white-glowing facades – from the imposing cathedral to the leaning tower you can climb.

☞ We wrote a separate guide to what to see in Pisa. It also includes a map, detailed information on sightseeing and restaurant tips.

Campo Santo Pisa / Pisa Italy Tuscany

Lucca

For lunch, transfer to the nearby town of Lucca. It has a more beautiful historic centre than Pisa and well-preserved city walls. What’s more, Lucca isn’t so touristy – you’ll often see mostly Italians and soak up the authentic atmosphere.

You can easily spend a few hours or even a whole day in Lucca.

lucca Basilica di San Frediano
Basilica di San Frediano, Lucca

Day 7: Montecatini Terme and Pistoia

Montecatini Terme

As the name suggests, Montecatini Terme is a spa town just half an hour’s drive from Lucca. Explore the Parco delle Terme, with its magnificent buildings and stunning views of the surrounding area.

Don’t miss the cable car that leads directly from the town to Montecatini Alto at the top of the hill with its beautiful historic core.

montecatini alto tuscany roadtrip
Montecatini Alto

Pistoia

End your day and your entire stay in Tuscany in the town of Pistoia, an underrated jewel of Tuscany.

At the heart of the historic centre is Piazza del Duomo, where the magnificent San Zeno Cathedral is located, with its splendid interior. On its left side is the bell tower, where you can climb for the best view of the city. The historic Ospedale del Ceppo Hospital is a short walk away.

Pistoia is not a big place, it will take you only a few hours to visit. Paid parking is available near the centre, and Parcheggio Pertini is a good choice.

pistoia

ITINERARY 3: SOUTH OF TUSCANY

5-6 DAY ROADTRIP IN TUSCANY

  • Day 1: Siena
  • Day 2: Crete Senesi – Montepulciano
  • Day 3: Val d’Orcia – Pienza – Montalcino
  • Day 4: Terme San Filippo – Sorano
  • Day 5: Saturnia – Pitigliano
  • Day 6: Maremma Regional Park – Monte Argentario

Day 1: Siena

We have written a lot about Siena in this article. It lies in the heart of the region, so you can easily include it in your itinerary for both northern and southern Tuscany.

There’s a lot to see in Siena, so we’ll dedicate a full day to it in this itinerary. If you want to enjoy the best view of the city, stay for sunset.

Day 2: Crete Senesi – Montepulciano

In the morning we leave Siena and head for the Tuscan countryside. Our first destination is Crete Senesi, a beautiful area with cypress trees and rounded hills with local wineries scattered around. There are several stops along the way where you can stop, walk around and admire the surroundings.

crete senesi tuscany roadtrip

We then head to Montepulciano, a medieval town high up on a hill with a perfect view of the surrounding countryside. Enjoy the atmosphere, have lunch and explore the historic centre.

On the way, you can make a short stop in the charming village of Montefollonico. It will take you no more than an hour to visit.

Accommodation Tuscany 😴

ubytování toskánsko
Certosa di Pontignano Residenza d’Epoca

Wonderful accommodation in a former monastery

ubytování toskánsko
Bosco Della Spina

Infinity pool, Tuscan cuisine, beautiful view

Day 3: Val d’Orcia – Pienza – Montalcino

We are on our third day here and our destination is Val d’Orcia, a beautiful UNESCO listed area. Val d’Orcia is easy to get around by car or bike, and you can stop here and there to enjoy the views of the Tuscan countryside.

Then head to Pienza, a Renaissance town that will take your breath away with its beauty. Take a stroll along the ramparts with a view into the distance.

Pienza Tuscany Italy

The last place on our busy itinerary for the third day is Montalcino.

Montalcino has preserved its medieval character with narrow streets and historic buildings. You can visit the Fortezza di Montalcino, which offers stunning views of the surrounding countryside.

montalcino tuscany roadtrop / itinerary for tuscany

The town is world famous for its exceptional Brunello di Montalcino wine, considered one of the best and most expensive Italian wines. The town and surrounding area offers many wineries where you can enjoy tours and tastings.

Not far from here is the Abbey of Sant’Antimo – a lovely place for a short visit on the way.

☞ If you drive your own car, auto insurance provides you with car repairs, towing to a garage, transport back home or a replacement vehicle if needed.

Sant'Antimo Abbey
Sant’Antimo Abbey

Day 4: Terme San Filippo a Sorano

Amid forests and greenery is Terme San Filippo, a spa resort famous for its calcium-rich thermal springs that form natural limestone pools and cascades. The place is accessible free of charge.

Terme San Filippo tuscany

Then we head to Sorano, a medieval town carved into the tuff, which gives it the nickname “Matera of Tuscany”. With its narrow streets, steep cliffs and ancient houses, Sorano is a wonderful place to visit in southern Tuscany.

Sorano, Tuscany Italy

Day 5: Saturnia and Pitigliano thermal springs

You can find more information about both places in the first itinerary, which includes the best of Tuscany.

Saturnia Thermal Springs

In the village of Saturnia there are thermal springs, with clear blue and crystal clear water, where you can take a free bath in water at a temperature of around 37 degrees Celsius.

saturnia tuscany

The venue is completely free to access, with paid parking and refreshments 5 minutes away.

Just a few minutes’ drive from the thermal springs is Montemerano, a picturesque village with a well-preserved medieval centre. It will take you less than an hour to visit.

Pitigliano

In the afternoon, head to the town of Pitigliano, surrounded by deep gorges and dramatic volcanic tuff cliffs. Pitigliano is known as “La piccola Gerusalemme” or Little Jerusalem, thanks to its rich history of the Jewish community and its well-preserved synagogue.

pitigliano tuscany

Alternative: If you have less time, choose to visit just one of the thermal spots – Terme San Filippo or the springs in Saturnia, and add a visit to Pitigliano or Sorano.

Accommodation South Tuscany 😴

ubytování toskánsko
Agriturismo Le Cascatelle – Saturnia

Excellent cuisine, private beach, parking

ubytování toskánsko
B&B 8380 Saturnia Terme – Saturnia

Good price, parking, quiet environment

Day 6: Maremma Regional Park and Monte Argentario

Maremma Regional Park

On the last day of our itinerary we head to the sea. Marina di Alberese is located in the Maremma Regional Park and offers an unspoilt and unspoilt beach with dunes, pine forests and a sense of tranquillity. It is a protected area, known for its natural beauty and wildlife.

Tip: If you’re planning to rent a car, I recommend booking well in advance to ensure you get the best price and choice. In addition, Tuscany is very popular and last-minute availability can be very limited.

Monte Argentario Peninsula

Or head to the Monte Argentario peninsula for some of the most beautiful sunsets in Tuscany. With views of dramatic cliffs surrounded by greenery, it’s second to none.

monte argentario / tuscany itinerary

Head north towards the port of Porto Santo Stefano, where you can grab some delicious seafood. From here, head along the panoramic path along the coast. There are several options where you can stop, just to admire or follow the trail to the viewpoints and coves with pebble beaches (it’s marked). The perfect end to a busy itinerary in Tuscany.

The whole island can be circumnavigated – without stops, it will take you about 1.5 hours. Parking outside the harbour is usually free.

Alternative: If you have 5 days in Tuscany, skip the visit to the peninsula. It’s a beautiful place, but it’s not typical Tuscany.

monte argentario porto santo stefano / tuscany itinerary
Porto Santo Stefano / Itinerary for Tuscany

How to enjoy Tuscany

  • Take the regional roads, which are often narrow and winding, but on the other hand take you through the beautiful Tuscan countryside.
  • Visit the most popular places early in the morning or late in the afternoon, when the biggest crowds leave. San Gimignano, Pienza or Montepulciano have a completely different atmosphere.
  • If you don’t have your own car, I recommend renting one locally so you can drive around places like Val d’Orcia, medieval villages or the Saturnia thermal baths. It is a good idea to book as early as possible to ensure the best price and availability.
  • Enjoy accommodation in a Tuscan villa or Agriturismo in the countryside. Here, you’ll be best treated to local cuisine, excellent wine, and views of the rolling Tuscan countryside. They often have a pool where you can refresh yourself. We also have some tips for the best agriturismo or Tuscan villas in the article.
tuscany itinerary

These were our itinerary suggestions for things to do in Tuscany on a 5-7 day roadtrip. Do you have a question? We’ll be happy to answer it in the comments below. Have a safe journey!

More information about Italy

ITALY: Get inspired by the most beautiful places in Italy. In this article you will find more information on how to travel by train in Italy. Here are 5 sample itineraries of where to go in Italy by train (including a map and useful information).

ROME: Rome is one of the most popular cities in Europe. Here’s a list of the best things to see in Rome. Build your 3-day Rome itinerary and see how to save in Rome. Find out all about the Vatican Museums or the Colosseum.

VENICE: In the article What to visit in Venice we bring you tips on the most beautiful places and other useful tips.

NAPLES: Naples has one of the oldest historic centres in the world and many other beautiful places to see.

Read even more tips on travelling in Italy.

tuscany

FAQ: Tuscany itinerary: things to do in Tuscany on a 5-7 day roadtrip

What type of car is best to rent for a roadtrip in Tuscany?

For comfortable driving on Tuscan roads, I recommend a smaller to medium-sized car, which is better suited for narrow country roads and city parking lots.

What are things to do in Tuscany and what not to miss in an itinerary for Tuscany?

You should definitely visit Florence, the heart of Renaissance art and architecture. Don’t miss Siena with its fascinating historic centre, Pisa for its famous leaning tower and picturesque towns such as San Gimignano, Volterra and Montepulciano. For nature lovers, a drive through the Chianti countryside, famous for its vineyards and olive groves, the Val d’Orcia or the thermal springs of Saturnia is also an unforgettable experience.

When is the best time to go on a roadtrip in Tuscany?

The best time for a roadtrip in Tuscany is from May to June and then from September to October. During these months the weather is ideal, with temperatures that are not too high, and there are fewer tourists than during the main summer season. In addition, the landscape is decorated with blooming flowers in spring and golden vines in autumn, adding another dimension to the Tuscan experience.

If you’re going to Tuscany in summer, look for accommodation with a pool to cool off on hot days. Choose from rustic Agriturismo or modern resorts with full facilities.

What is the weather in Tuscany?

The weather in Tuscany during the spring and autumn months is usually mild with warm days and cooler evenings. It can rain occasionally, especially in spring, but the rains tend to be short and not very frequent. Temperatures can rise more significantly in summer, so if you’re planning a roadtrip during this period, be prepared for hot and dry days. On the other hand, you have an excuse to taste the best gelaterias in Tuscany.

What to watch out for when driving in Tuscany?

Driving in Tuscany is generally safe, but be careful on narrow country roads.
In some urban and rural areas there are restricted traffic zones (ZTLs) that are open only to local residents or licensed traffic.
In many historic city centres, parking is restricted or charged. I recommend using secure parking lots on the outskirts of towns and walking or taking public transport to the centre.

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