The Oldest Cities in Europe: How To Visit Them By Road

For most, the typical European vacation involves sightseeing at crowded tourist attractions, multiple flights, perhaps an expedition or two on the Eurail, and a general confinement to the heavily trafficed holiday destinations. But for those seeking a more adventurous trip across the continent––one that includes quaint villages, unexpected breath-taking views, and out of the way locations––traveling by road is a much better option. This Mediterranean route will take you through some of Europe’s oldest and most culturally significant cities, giving you the opportunity to experience the region with an intimacy that few can ever attain.

Lisbon, Portugal

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You’ll start your journey in Lisbon––Portugal’s hub of culture, economics, and art––at the farthest Western edge of Southern Europe. The oldest city in Western Europe, Lisbon was originally founded by Pre-Celtic tribes who built monuments and megaliths still standing today. Archeologists have even unearthed artifacts from Phoenician cultures dating back to 1200 BC. Subsequently ruled by Germanic tribes in the 5th Century BC, Moors in the 8th century BC, and even Julius Caesar during the height of the Roman Empire, Lisbon has a rich historical background.

Be sure to check out Belem Tower and Jeronimos Monastery (UNESCO World Heritage Sites) before embarking on your inaugural drive through Portugal’s Alentejo region, Beja, Serpa (a gorgeous town for a stopover), and Seville (thanks to recent European Union regulations, border crossings are a cinch) on your way to…

Cadiz, Spain

Image source: Sixt (Driving in Europe)

A member of the Most Ancient European Towns Network, Cadiz is the oldest city in the Iberian Penninsula. Founded by Phoenicians in 1104 BC, it was later controlled by the Greeks (whose legend avers that Hercules founded the city), Hannibal, the Roman Empire, and eventually the Visigoths.

Explore the tortuous alleys of Old Town, tour the famous Plazas, and check out the ancient city walls of Andalusia before hitting the road again. The beautiful coastal route will take you past the Strait of Gibraltar, from the bank of which you can spot Morocco on a clear day; and after about 3 hours you’ll arrive in…

Malaga, Spain

Founded by Phoenicians in 770 BC, Malaga was later controlled by Carthage, Rome, the Visigoths, and the Byzantine Empire––all of whom left their unique imprints on the city. The birthplace of Pablo Picasso and Antonio Banderas, this Spanish city is rich in museums, theatres, cathedrals, and stunning architecture (old and new). Like Cadiz, it is also host many ancient ruins, including remnants of centuries-old defensive walls.

After soaking up the serenity of Malaga, it is time to head north along the Spanish coastline. Break up the trip with stops in Granada, Cartagena, and Valencia along the way, until (after about 10 hrs on the road) you roll into the bustling streets of…

Barcelona, Spain

Spain’s 2nd largest city, and home to the world-renowned F.C. Barcelona, Barcelona is a booming cultural center. The famous city was founded in the 3rd century BC by the Carthaginian General who would later become Hannibal’s father.

Take in Gaudi’s cathedrals, world-class museums, dozens of UNESCO World Heritage Sites, the infamous nightlife, and all the tapas you can eat. Then, after passing through Perpignan and the quaint villages of Coullioure and Ceret, it is onward to…

Marseilles, France

Image source: Sixt (Driving in Europe)

This important port city and cultural hub is France’s 2nd largest city. Paleolithic cave paintings dating back to 25,000 BC indicate that this picturesque coastal region (bordered by the Garlaban and Etoile mountain ranges) is likely the oldest human settlement in France. It was officially founded as a city by the Greeks in 600 BC, and would later come under the rule of Julius Caesar.

After being awed by the catacombs, cathedrals, museums, and impressive diversity of architectural masterpieces, it is time to head north, turning your back on the Mediterranean for an excursion through Avignon, Montelimar, Geneva, and Berne on the way to…

Zurich, Switzerland

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Early settlements here date back more than 6400 years to the Neolithic and Bronze Ages. In 15 BC Romans took control of the important trade city, and in more recent history Zurich became the origin of the Protestant Reformation in Switzerland. In addition to housing UNESCO pre-historic pile dwellings, Zurich has also been the home of numerous intellectual luminaries including Richard Wagner, Albert Einstein, and James Joyce.

Upon leaving the city recognized by Monocle 2012 for providing residents with the Best Quality of Life in Europe, you’ll traverse a gorgeous route south through the Swiss Alps, Como, Milan, Parma, Bologna, and Florence, before finally arriving (after about 10 hrs drive time) in…

Rome, Italy

Image source: Sixt (Driving in Europe)

Though commonly celebrated as “The Eternal City,” Roman civilizations can be traced back to 753 BC. This storied and internationally celebrated former capital of the Roman Empire needs little introduction.

Be sure to see the Sistine Chapel, the Coliseum, Vatican City, and to eat your fill of gelato before getting back into the car for the next 2-hour leg of the journey to…

Naples, Italy

Settled by Bronze Age Greeks in the 2nd millennium BC, Naples is one of the oldest cities in Europe. A UNESCO World Heritage City, it is close to Pompeii, and home to countless awe-inspiring cobblestone piazzas, medieval castles, ancient palaces, and important art museums.

You’ll be tempted, as most who come here are, to stay quite a while. But when you finally bring yourself to resume the journey, you’ll embark on a 6-hour drive along E-45, through Salerno, and onward to the tip of the Italian boot, where you’ll board a ferry for…

Messina, Sicily

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Messina was founded by Greeks in the 8th century, then sacked by Carthage in 397 BC, and eventually controlled by Goths, Byzantines, Arabs, Normans, and even Richard “The Lionheart” I of England. Having long been an important port city in the heart of the Mediterranean, it is believed that Messina also played a significant role in the fate of modern Europe––as the port where the Black Plague first entered the continent.

Admire the ancient churches, storied ruins, rich museums, and gorgeous coastal seascape before departing for your final leg of the trip, which will take you just two more hours south to…

Syracuse, Sicily

Another UNESCO World Heritage City, Syracuse has been a key city throughout ancient history. It was first established by Greeks in 734 BC, and later occupied by Roman and Byzantine forces. Today, it is home to a diversity of ancient masterpieces, including the Necropolis of Pantalica, the Fountain of Diana, numerous Roman amphitheatres, and many other architectural wonders. Syracuse is also famously the birthplace of Archimedes.

But most importantly, Syracuse is a stunning seaside island city: the perfect place to relax and reflect on your long journey.

By now, you’ve traveled more than 5000 km through five countries and many of the most historic cities in Europe, and been on the road for a total of about 50 hours. Having spent roughly €800 on petrol, and a significant amount on tolls––not to mention the many other travel expenses––it is probably time to get back home and back to work. But for now, you won’t think about that. You’ll be far too busy basking in the sunshine on the Sicilian coast, sipping wine, and soaking up the last few days of your unforgettable adventure.

Featured images:

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  •  License: Creative Commons image source 
  •  License: Image author owned 
  •  License: Creative Commons image source 

This article was written by Alfie Davenport, a Europe road trip enthusiast who prefers the slow route across this beautiful and fascinating continent.