MORNING BIRD TRAIL

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Tuscany is arguably one of the most beautiful states in Italy. Home to postcard-like cities like Florence, Pisa, Livorno or Siena, with tons of history and beauty to explore.

If Tuscany is your ultimate place to go on an epic road trip between vineyard and olive trees, you came to the right place. In this blog post, I’m going to inspire your next Italian road trip with this perfect itinerary around the beauty of Tuscany. The blog post will show you a two-week itinerary around the region of Tuscany, Italy, where we will enjoy all of what Tuscany has to offer.

Overview

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Considerations

When you want to choose where you want to drive, there are some considerations to be done. In Tuscany, you may want to remember that, in some parts of the less known areas, your internet connection may fail. This means that you should probably have an offline or paper map with you just in case the connection fails and you get lost on your drive.

Usually, the most scenic roads, the ones that you probably are more interested in driving, are those that are more narrow and winding and where the maximum velocity is lower. If you rather not drive on these roads, you can also take highways and larger roads, but you probably will be passing by the Tuscany landscape that you imagined without seeing it.

In Tuscany, usually, the highways are paid and are marked with green signs. These are quick roads where you can drive at 130km/h speeds. You can also find free larger roads, the superstrade ,where you can drive at 90km/h usually.

How to get there?

In Tuscany, there are two international airports, Pisa and Florence. Usually, European low-cost airlines (but not only low-cost ones) fly to Pisa while the other ones fly to Florence. Nonetheless, you can fly to any of these airports and even others in close by cities such as Rome and Bologna.

Despite the airport of your choice, you can either rent a car at the airport or in one of the cities. If you chose to rent a car in a city such as Florence, it is really easy to go from any of the airports to the city by bus and/or train.

Another thing that you may want to consider is that you don’t need a car to explore Florence or any of the major cities. The attractions are all close by, and it’s way better to walk around the city than to drive. Some of the cities, for example, Florence, don’t even allow cars in the city centre. Because of this, it may be better for you to pick the car on your last day in the city.

Day 1 – From Florence to Arezzo

This road trip starts in Florence, on your last day in the city. If you want to get inspired to travel the city, you can check my 23 top things to see in Florence, Italy blogpost. After packing all your things and getting your car, you’ll start to drive east until you get to Poppi.

Poppi is part of the Province of Arezzo and is 1h40 away from Florence. The main attraction of this town is its 12th-century castle, the Castello dei Conti Guidi, resembling Palazzo Vecchio in Florence. This is a well preserved medieval town and still has its original Medieval porticos. Other attractions in the town include the adorable baroque style Madonna del Morbo church, located in the lovely piazza Amerighi.

From here, we head to Borro, an adorable tiny village on top of a hill where the time seems to have stopped. The drive from Poppi to Borro takes around one hour through fields of Tuscan beauty. This village was bought in 1993 by the Ferragamo family that restored the houses and built an imponent villa. In the village, you can also find a luxury hotel and spa.

Very close to Anghiari, only 10 minutes away driving, you can find Sansepolcro, a town founded in the 11th century. The advantage of this city is that it is way flatter than many other medieval towns such as the previous ones.

From this city, we head to our final destination of the day, Arezzo, where we will stay the night. This city is located around 40 minutes away from Sansepolcro by car, so you’ll get there at night.

Day 2 – Full day in Arezzo

Arezzo is the biggest city in this part of Tuscany and is located on a steep hill. Because of this, the easier way to explore is starting at the top of the city. You can park in the Parking Pietri. Near this parking lot, you can explore the Cathedral and a beautiful park, the Passeggio del Prato. The Cathedral is a very imponent monument, visible for miles in the countryside. Right at the end of the park, you can also visit the Fortezza Medicea. This fortress has a shape of a five points star and was built by Cosimo I to reinforce the Florentine dominance in the city.

There are several palaces in the city such as Albergotti Palace, Palazzo Dei Priori, Palazzo Fossombroni and many others.

In the Piazza Grande, you can find a Loggia designed by Vasari, the same architect that designed the Vasari Corridor, over Ponte Vecchio in Florence and renovated the churches of Santa Maria Novella and Santa Croce in the same city. What is special about this square is its slope, designed to funnel off the water.

There are many other things to visit and streets to wander until you find yourself in the Roman Amphitheatre. This monument is not like the Coliseum in Rome, it is way more degraded, being more like a ruin. However, this amphitheatre once held around 13000 persons. If you want to learn more about the Roman Amphiteatre, the Roman history in Arezzo, and also the history of the city, you can also check the Archaeological Museum. In this museum, you can even see a reconstruction of the amphitheatre.

Day 3 – from Arezzo to Mintepulciano

From the city of Arezzo, we keep going south in the direction of Cortona. Cortona is located less than 1 hour away from Arezzo. Between the two cities, you’ll pass through towns such as Rigutino and Montecchio where you can stop for a while and appreciate the view from the Castello di Montecchio Vesponi, for example.

Cortona is enclosed by ancient stone walls and, like many towns and cities in Tuscany, also sits on top of a hill. This means that you can get an amazing view of the valley and the close by Lake Trasimeno (our next stop). This cute medieval town has narrow and steep streets where you can wander and appreciate the landscapes. You can also go on a cooking class in Cortona!

Lake Trasimeno is located half an hour away from the town. This lake is the border between Tuscany and the neighbour region of Umbria. The beautiful blue lake has three islands, one of them inhabited by a small community of fishermen. On this island, you can also identify the ruins of an old Franciscan monastery from the 14th century. Around this lake, you can also find beaches where you can enjoy a few hours by the sun, such as Zualzo Beach or the Spiaggia di Tuoro Sul Trasimeno. The majority of these activities are outside Tuscany, but they are still a good idea to do since you are so close to them.

Back to the Region of Tuscany, we head to Montepulciano. This town is located 40 minutes away from Castiglione del Lago, on the shores of Lake Trasimeno. The town of Montepulciano is full of Renaissance palaces and beautiful panoramic views of the Val d’Orcia and Val di Chiana. We will spend the rest of the day in this astonishing city and will enjoy beautiful walks around the town and all its hidden corners.

One of the best places to appreciate the incredible vastness of the valleys is on the top of the tower of the Palazzo del Comune. All around the town, you can also see sumptuous residences and buildings in the historic centre If you are visiting the town during Summer, pay attention to the events that may be occurring there. Some of these events include the International Arts Workshop, the Bruscello and the Bravio delle Botti, an original race competition with wine barrels.

Day 4 – Montepulciano to the hot springs of Bagni San Filippo

After a night well slept in Montepulciano we head to another village on the top of a hillAfter a night well slept in Montepulciano, we head to another village on the top of a hill, Pienza. Pienza is 20 minutes away from Montepulciano and to get there you’ll have to drive on little countryside roads. This village is known as the ideal city of the Renaissance and in 1996 was declared UNESCO World Heritage Site, before the entire Val d’Orcia, in 2004. The village was requalified by Piccolomini that had the money and influence to create his dream city. In only 3 years, the central square, with its Cathedral, Piccolomini Palace and the Town Hall, was built.

The next step in this Tuscany road trip is Montalcino, half an hour away. On the road between Pienza and Montalcino, you’ll also find the Cipressi di San Quirico d’Orcia, an example of the typical Tuscan landscape that we are used to seeing. This town also has narrow and steep streets with incredible views on the top. One of the most famous wines, Brunello di Montalcino comes from this region so you may also want to taste a bit of it while you are there.

After the stop in Montalcino, we will end our day at the first hot spring of this Tuscany road trip, the Bagni San Filippo hot spring. In this village, you’ll see the amazing White Whale waterfall. This is an incredibly massive white limestone rock in the forest with hot thermal waters. You can enjoy a spa bath or hike around the place for a breathtaking sunset adventure. The best part? All of these activities are completely free!

You may want to look at close-by villages and towns to spend the night, some of these towns and villages include Abbadia San Salvatore, 20 minutes away from the hot spring, Rifugio Cantore 30 minutes away and many other places where you can rent a room or an entire villa for the night.

Day 5 – Heading towards Capalbio

Our first stop today is the Le Vie Cave, around Sovana, Sorano and Pitigliano. These are roads that were carved in the limestone many years ago, during the Bronze age. These roads are on the watchlist of endangered monuments because of their fragility since the rock can easily be eroded. In the Summer, when the region is super warm, this walk is very refreshing because of the shade of the stones. You can inclusively go From Pitigliano to Sovana through the Vie Cave. If you want to hike, for example, the Via Cava di San Giuseppe or the Via Cava di Fratenuti, you should expect to spend at least 2h30 hiking the circuit (round trip).

After this, you may want to go to Pitigliano to have a great Italian lunch. In the town, you can see many remains of the Bronze age, Neolithic and also Copper Age that were found in the region. You can also find ruins of a necropolis and temple from the Etruscan community.

From Pitigliano, we head to another relaxing afternoon at Terme di Saturnia at the Cascate del Mulino, half an hour away from Pitigliano. This is the most famous hot spring in Tuscany and resembles the incredible Turkish hot springs of Pamukkale. Access to these pools are free and can be done throughout the year.

After leaving the hot spring, you can head to the lovely village of Capalbio where you can stay the night. This village is one of the hidden gems of Tuscany. To enter the village you pass through ancient gates to find the narrow streets and stone arches so typical of this region. The village isn’t far from the sea so you can enjoy views from both the Maremman countryside and the Mediterranean sea.

Day 6 – Beach day in Monte Argentario and Giglio Island

Today, we will spend the day enjoying what the Mediterranean sea has to offer. After you decide that it’s time to move away from the beauty of Capalbio, we keep moving in the direction of Orbetello’s lagoon area. You can even take a walk through Feniglia, a 6km long strip of sand, between the Ansedonia hill to the east and Monte Argentario to the west.

The objective of this drive is to get to Porto Santo Stefano, 45 minutes away from Capalbio. Porto Santo Stefano is the largest seaport town in Monte Argentario. Like many seaport towns, here you can find a marina with yachts but you can also find colourful houses perched on the promontory.

From this town, the departure point for the ferries to Giglio Island and Giannutri Island. Knowing this, we come to Porto Danto Stefano, not only to explore the town but also to take one of these ferries to Giglio Island.

To get to the Island from Porto Santo Stefano you can take a ferry from either Toremar or Maregiglio which will cost around 14€. In Giglio Island, you will find a pretty self-sufficient city. Much of the area of the island is unspoiled and there are many rare animals over there. The best way to navigate the island is by bus but you can also bring your car from the mainland.

After a great day exploring the seaside beauties, we keep moving in the direction of Grosseto, where we will spend the night. Grosseto is located 45 minutes away from Porto Santo Stefano and is a major Tuscany city.

Day 7 – Grosseto and Follonica

This is a city that is also closed to the sea, just 14km away from it. For the next couple of days, we will keep the road trip close to the shore. This city also is more recent than other historic villages in the region.

Many tourists don’t choose to come to Grosseto, which is something a bit rare in Tuscany, and Italy. Because of the lack of tourists, this city has the perfect ambience for a relaxed walk around its cute streets.

The historical centre of Grosseto is surrounded by medieval walls that were ordered to be built by the Medici family in the 16th-century and are still well preserved. In the city, you can also find the Archeological Museum and the beautiful Dante Alighieri square, where you will also find the Cathedral of San Lorenzo.

After this beautiful and calm walk around Grosseto, you will go back to the beach, 40 minutes away from Grosseto, to the town of Follonica. Follonica is a town by the beach, in a beautiful bay, where you can spend the rest of the afternoon relaxing. If you don’t want to just stay on the beach enjoying the sun and the warm water, you can also hike in the trails, through the Mediterranean shrub, and even reach the wonderful Cala Violina beach.

You can spend the night in Follonica or half an hour away in the town of Piombino, the first stop of tomorrow.

Day 8 – Piombino to Livorno

Today we keep moving north, near the sea, until we reach the city of Livorno. The drive from Piombino to Livorno is 1h30 and from Follonica is 2 hours. During this route you will find many beaches where you can stop for a while, that is why today will be a slower day so that you can enjoy the beautiful Italian coast and the incredible Mediterranean water.

Even if you slept yesterday in Piombino, you probably haven’t explored much of the town. Piombino is located in a promontory, and is one of the main cities of the Etruscan Coast. Here you can find several ancient artefacts at the archaeologic museum and in the Parks of the Val di Cornia of the city. You can also find several works by Leonardo da Vinci such as in Palazzo Nuovo, inside the Cittadella. Here you can also find amazing beaches such as in the Sterpaia Nature Park.

From here to Livorno you pass through some coast towns such as Cecina and San Vincenzo.  Where you can stop and spend a few more hours in the sea if you wish.

We will stay in Livorno for tomorrow and the rest of today to have all the time needed to explore the city.

Day 9 – Full day in Livorno

Livorno is the third-largest city in Tuscany and you will be welcomed there by the colourful houses looking at the sea. You will explore bridges, canals, beautiful streets and historical places. The city was one of the main ports in Europe in the 16th century.

In Livorno, you can appreciate the view of the sea and amazing sunsets in the Mascagni Terrace, a beautiful square with a black and white checkered floor near the sea where you can appreciate the Mediterranean views. You can also see the Old Fortress with the Mastio di Matilde near the port. This Fortress is also connected to the New Fortress, in the city centre by waterways.

This city is also home to some beautiful squares, so typical of Italian cities. Some of these squares are the Piazza delle Repubblica and the Piazza Grande where you can enjoy a refreshing gelatto (ice cream) on a warm day.

You can in Livorno you can head to the Little Venice, where you can get on a boat trip to the Renaissance places in the city centre.

In Livorno, you can also explore several very different museums and churches, but also explore the Romito, Quercianella caves and the sea in the Calafuria nature reserve. Or explore the incredible nature in Livorno Mountain Park.

Day 10 – Pisa and Lucca

From Livorno, we keep driving north to the postal-like city of Pisa, 40 minutes away from Livorno. Pisa doesn’t need any introductions. The most famous landmarks are the Leaning Tower of Pisa and the Piazza dei Miracoli that surrounds it. This square includes the Battistero di San Giovanni and the Cattedrale di Pisa. This Square is also a UNESCO World Heritage site since 1987 and is a favourite stop for many tourists in Tuscany. If you want to climb to the top of the Leaning Tower of Pisa you may want to buy the tickets in advance, especially in the high season. Besides this, Pisa also has other beautiful places to see, such as the Piazza dei Cavalieri, the Piazza Vittorio Emanuele and the bridges over the Arno river.

Less than half an hour away from Pisa we’ll get to Lucca. Lucca is nicknamed the town of a hundred churches because of the many churches that can be found in the town. Lucca is also one city that is surrounded by walls, built in the 16th and 17th centuries. You can walk on these walls and enjoy a view of the city from there. We will spend the night in the town and tomorrow we will explore everything else that the town has to offer. 

Day 11 – Full day in Lucca and the surrounding Villas

You can also explore the city in this 2-hour walking tour where all its history is explores. The Guinigi tower, a tower with more than 700 years, is one of the remaining towers of Lucca and is special because it has a cute garden at its summit that almost looks like hair on the tower. The family that built the tower, the Guinigi family, planned the garden to represent rebirth and renewal.

Close by to Lucca, you can find many beautiful gardens in the region. Some of these are those located in the Villa Reale di Marlia, 20 minutes away from Lucca, where Napoleon’s sister once lived. Next is Villa Mansi, 11 minutes away from Villa Reale di Marlia and 25 from Lucca. Here you can see the beautiful architecture and an English garden. One last wonderful villa to explore is the Villa Torrigiani, 25 minutes away from Lucca and 5 minutes away from Villa Mansi.

In Lucca, you can also experience several events, depending on the time of the year when you are doing this Tuscany Road Trip. In July, you can see several concerts while in October or November you can go to the Lucca Comics & Games, when the city becomes a sort of cartoon-land.

Day 12 – From Lucca to Siena

After the city and beautiful villas with unbelievable gardens, we leave Lucca in the direction of Siena.

From Lucca, our first stop is in Buti, 35 minutes away. In the heart of the town of Buti, you find the famous Medici Villa. However, Buti has more to see in its narrow streets. Some of its landmarks are the Castel Tonini that has a great view of the city, the Romanesque Church of San Francesco and the Church dell’Ascensione, also known as Santa Maria delle Nevi.

After the stop in this cute town, we keep driving to Lari, 35 minutes away from the previous town. The most important landmark in Lari is the Castello dei Vicari. Other things to see in the city include the Oratorio della Madonna della Neve, the Casciana Alta and the house of Eusebi Valli, the scientist that developed rabies serum.

From here we go to the Teatro del Silenzio, another 35 minutes away from Lari. This is an open-air amphitheatre in the hometown of Andrea Bocelli. This amphitheatre is cute because it is located in the middle of the fields and even though it is a recent building, it seems quite ancient and with sculptures all around it.

After this quick stop, we head to San Gimignano, where we’ll get after a 45-minute drive. We can call the town of San Gimignano “the medieval Manhatten” because of all the towers that rise on the horizon while you keep getting close to the city. This town is also UNESCO World Heritage Site since 1990. There are today 13 towers in the town but once there was up to 65 of them. Beyond the towers, in San Gimignano, you can explore the cathedral, the Palazzo Comunale (an art gallery), the Torre Grossa, the tallest one, built in the 14th century and still standing today. You can, like in many other places in this Tuscany road trip, taste wine at the Vernaccia di San Gimignano Wine Experience – La Rocca.

The last stop for today (before getting to Siena) is Monteriggioni. Monteriggioni is 30 minutes away from San Gimignano and is a beautiful village surrounded by a beautiful and extremely well maintained 13th-century wall. A fun fact about Monteriggioni is that it is mentioned in the Devine Comedy. On the top of the towers in the wall, you can also appreciate an incredible panorama of Siena.

From Monteriggioni, we’ll drive our last 21 km of the day to get to the city of Siena, where we will spend the entire day, tomorrow.

Day 13 – Full day in Siena

Siena is a beautiful Medieval city that spreads for three hills. There is a lot to do in Siena and the most famous landmark is probably the central piazza known as  Piazza del Campo. Here, in the Summer, there is a famous horse race caller Palio di Siena. The Piazza del Campo is located between the three hills, where once the Roman Forum was. In this square, you can see the Pallazzo Pubblico with its Torre del Mangia, the Loggia della Mercanzia and also the Palazzo Piccolomini in Siena.

Another square that you can explore in Siena is the Piazza del Duomo. Here you can explore the Cathedral, the Crypt and also the Piccolomini Library. The Duomo of Siena, the Cathedral of Santa Maria Assunta its as beautiful inside as it is outside and is an example of Romanesque-Gothic churches, probably the most outstanding one in Italy. The Piccolomini Library is located inside the duomo behind a small door on the left side of the church. In Siena, you can also visit the Baptistery, entering from Piazza San Giovani.

Near the Duomo, you can also see the Santa Maria della Scala, one of the oldest hospitals in Europe. The complex is quite big so, if you want to visit it completely, it may take a while.

Day 14 – From Siena back to Florence

Today is the last day of our Tuscany Road Trip, but there are still many places to see and explore! We will drive back north to Florence today, but on the way, we will stop in places such as the Castello di Ama or Montefioralle.

After one last goodbye to Siena, we will drive to Castello di Ama. This is a 40-minute drive. In the castle, you can taste the wines produced in the region and take a guided 1h30 walk-in Ama. You can do this at the castle for 50€. The castle is also a hotel so you may consider this as one of your places to stay a night if you wish.

From Castello di Ama we drive another 40 minutes to get to Montefioralle another village on the top of a hill. This is one of the most ancient villages of the Chianti area and is considered one of the most beautiful villages in Italy. A special particularity of the town is that some of the houses are inside the old towers that were part of the original medieval town. On the top of the village, you can visit the church of Saint Stefano and admire the artwork in it. From the village, you can also appreciate the incredible view of the vineyards and the surrounding fields.

Before going back to Florence and finishing this road trip around Tuscany, we will lastly stop at Greve in Chianti. This town is located close to Montefioralle, less than 10 minutes away by car. The most famous landmark is the triangular-shaped square of Piazza Matteotti, surrounded by arched loggias with shops. In this square, you can find a large statue of Giovanni Verrazzano and the church of Santa Croce. You can also visit the wine museum in the town.

The last time that we will drive our rented car on this Tuscany road trip is to get back to Florence. Florence is located 40 minutes away from  Montefioralle and is our last stop in this Tuscan circular road trip that took us two weeks and showed us the beauty of the region.

If you want to learn more about what the city of Florence has to offer (and it is so so much), you can see 23 of these things in my blog post 23 top things to see in Florence, Italy. This article may be super useful if you decide to spend a few more days in the city after the end of this two weeks Tuscany road trip.

Full itinerary map:

In case you are wondering, all these pictures were taking with the following equipment:

• Canon EOS 90d
• Samsung SD card
• Canon EF 50mm F1.8 STM
• Canon EF-S 55-250mm F/4-5.6 is STM
• Canon  EF-S 10-18mm F/4.5-5.6 IS STM
• K&F Concept K-Serie 67mm ND Filter
• Samsung Galaxy A52 5G

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